MiMeDB: Showing metabocard for UDP-N-Acetylmuramyl-L-Ala (MMDBc0030160)

Microbial

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:56:18 UTC

Update Date

2022-08-31 17:40:16 UTC

Metabolite ID

MMDBc0030160

Metabolite Identification

Common Name

UDP-N-Acetylmuramyl-L-Ala

Description

UDP-n-acetylmuramyl-L-Ala is a precursor to peptidoglycan synthesis. UDP-N-acetylmuramoyl-L-alanine (UDP-MurNAc-L-Ala), which is the nucleotide substrate of the D-glutamic-acid-adding enzyme (the murD gene product) catalyzes key steps in the pathway for peptidoglycan synthesis. (PMID 8098327 ) MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). (PMID 19007109 ) The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05301214492D          

 60 62  0  0  0  0            999 V2000
    5.3184   14.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170   11.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   11.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024    9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315   14.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8039   12.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6654   11.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893    9.8372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7615    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2962    3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631   10.9413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4608   10.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0964    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8477   11.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9754   13.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7162   14.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   13.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   11.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    4.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    5.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308    8.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   10.4314    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   10.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   13.6171    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.8877   15.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3293   13.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    7.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    8.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    9.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    7.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   12.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069    9.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    8.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    8.0105    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    9.0724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1031   14.9340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   12.5131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   10.3451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    7.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9483   11.7583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    7.7819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2257   10.3351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   11.9247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    6.0381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   10.6864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  1  0  0  0
 10  3  1  4  0  0  0
 11  6  1  1  0  0  0
 12  7  1  1  0  0  0
 13  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 22 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 19  2  0  0  0  0
 25 10  2  0  0  0  0
 14 25  1  6  0  0  0
 26 13  2  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 20 27  1  1  0  0  0
 27 23  1  0  0  0  0
 28  6  1  0  0  0  0
 29 10  1  0  0  0  0
 30 13  1  0  0  0  0
 15 31  1  6  0  0  0
 16 32  1  6  0  0  0
 17 33  1  6  0  0  0
 19 34  1  4  0  0  0
 35 21  2  0  0  0  0
 36 21  1  0  0  0  0
 37 23  2  0  0  0  0
 42  7  1  0  0  0  0
 43  9  1  0  0  0  0
 18 43  1  1  0  0  0
 44 12  1  0  0  0  0
 44 20  1  0  0  0  0
 45 11  1  0  0  0  0
 45 22  1  0  0  0  0
 46 22  1  0  0  0  0
 48 38  1  0  0  0  0
 48 39  2  0  0  0  0
 48 42  1  0  0  0  0
 48 47  1  0  0  0  0
 49 40  1  0  0  0  0
 49 41  2  0  0  0  0
 49 46  1  0  0  0  0
 49 47  1  0  0  0  0
  8 50  1  1  0  0  0
  9 51  1  6  0  0  0
 11 52  1  6  0  0  0
 12 53  1  6  0  0  0
 14 54  1  1  0  0  0
 15 55  1  1  0  0  0
 16 56  1  1  0  0  0
 17 57  1  1  0  0  0
 18 58  1  6  0  0  0
 20 59  1  6  0  0  0
 60 22  1  0  0  0  0
M  CHG  3  29  -1  30  -1  34  -1
M  END


  Mrv0541 05301214492D          

 60 62  0  0  0  0            999 V2000
    5.3184   14.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170   11.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   11.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024    9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315   14.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8039   12.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6654   11.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893    9.8372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7615    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2962    3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631   10.9413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4608   10.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0964    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8477   11.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9754   13.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7162   14.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   13.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   11.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    4.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    5.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308    8.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   10.4314    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   10.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   13.6171    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.8877   15.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3293   13.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    7.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    8.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    9.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    7.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   12.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069    9.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    8.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    8.0105    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    9.0724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1031   14.9340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   12.5131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   10.3451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    7.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9483   11.7583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    7.7819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2257   10.3351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   11.9247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    6.0381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   10.6864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  1  0  0  0
 10  3  1  4  0  0  0
 11  6  1  1  0  0  0
 12  7  1  1  0  0  0
 13  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 22 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 19  2  0  0  0  0
 25 10  2  0  0  0  0
 14 25  1  6  0  0  0
 26 13  2  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 20 27  1  1  0  0  0
 27 23  1  0  0  0  0
 28  6  1  0  0  0  0
 29 10  1  0  0  0  0
 30 13  1  0  0  0  0
 15 31  1  6  0  0  0
 16 32  1  6  0  0  0
 17 33  1  6  0  0  0
 19 34  1  4  0  0  0
 35 21  2  0  0  0  0
 36 21  1  0  0  0  0
 37 23  2  0  0  0  0
 42  7  1  0  0  0  0
 43  9  1  0  0  0  0
 18 43  1  1  0  0  0
 44 12  1  0  0  0  0
 44 20  1  0  0  0  0
 45 11  1  0  0  0  0
 45 22  1  0  0  0  0
 46 22  1  0  0  0  0
 48 38  1  0  0  0  0
 48 39  2  0  0  0  0
 48 42  1  0  0  0  0
 48 47  1  0  0  0  0
 49 40  1  0  0  0  0
 49 41  2  0  0  0  0
 49 46  1  0  0  0  0
 49 47  1  0  0  0  0
  8 50  1  1  0  0  0
  9 51  1  6  0  0  0
 11 52  1  6  0  0  0
 12 53  1  6  0  0  0
 14 54  1  1  0  0  0
 15 55  1  1  0  0  0
 16 56  1  1  0  0  0
 17 57  1  1  0  0  0
 18 58  1  6  0  0  0
 20 59  1  6  0  0  0
 60 22  1  0  0  0  0
M  CHG  3  29  -1  30  -1  34  -1
M  END
> <DATABASE_ID>
MMDBc0030160

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C([O-])=N[C@]([H])(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/p-3/t8-,9-,11-,12-,14-,15-,16-,17-,18-,20-,22?/m1/s1

> <INCHI_KEY>
NTMMCWJNQNKACG-JKXSCJIPSA-K

> <FORMULA>
C23H33N4O20P2

> <MOLECULAR_WEIGHT>
747.4704

> <EXACT_MASS>
747.11633754

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
63.69122935071273

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(1R)-1-carboxyethyl]-2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}propanecarboximidate

> <ALOGPS_LOGP>
-1.14

> <JCHEM_LOGP>
-3.1245791570000003

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.986712278153094

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7263620426244408

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6645543264939358

> <JCHEM_POLAR_SURFACE_AREA>
374.7700000000001

> <JCHEM_REFRACTIVITY>
183.2002000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(1R)-1-carboxyethyl]-2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}propanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   49  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   50  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   13                                                       
CONECT    5    4   27                                                       
CONECT    6   11   28                                                       
CONECT    7   12   42                                                       
CONECT    8    1   21   24   50                                             
CONECT    9    2   19   43   51                                             
CONECT   10    3   25   29                                                  
CONECT   11    6   16   45   52                                             
CONECT   12    7   15   44   53                                             
CONECT   13    4   26   30                                                  
CONECT   14   18   22   25   54                                             
CONECT   15   12   17   31   55                                             
CONECT   16   11   18   32   56                                             
CONECT   17   15   20   33   57                                             
CONECT   18   14   16   43   58                                             
CONECT   19    9   24   34                                                  
CONECT   20   17   27   44   59                                             
CONECT   21    8   35   36                                                  
CONECT   22   14   45   46   60                                             
CONECT   23   26   27   37                                                  
CONECT   24    8   19                                                       
CONECT   25   10   14                                                       
CONECT   26   13   23                                                       
CONECT   27    5   20   23                                                  
CONECT   28    6                                                            
CONECT   29   10                                                            
CONECT   30   13                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   19                                                            
CONECT   35   21                                                            
CONECT   36   21                                                            
CONECT   37   23                                                            
CONECT   38   48                                                            
CONECT   39   48                                                            
CONECT   40   49                                                            
CONECT   41   49                                                            
CONECT   42    7   48                                                       
CONECT   43    9   18                                                       
CONECT   44   12   20                                                       
CONECT   45   11   22                                                       
CONECT   46   22   49                                                       
CONECT   47   48   49                                                       
CONECT   48   38   39   42   47                                             
CONECT   49   40   41   46   47                                             
CONECT   50    8                                                            
CONECT   51    9                                                            
CONECT   52   11                                                            
CONECT   53   12                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   18                                                            
CONECT   59   20                                                            
CONECT   60   22                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

Synonyms

Not Available

Molecular Formula

C₂₃H₃₃N₄O₂₀P₂

Average Mass

747.4704

Monoisotopic Mass

747.11633754

IUPAC Name

(2R)-N-[(1R)-1-carboxyethyl]-2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}propanecarboximidate

Traditional Name

(2R)-N-[(1R)-1-carboxyethyl]-2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}propanecarboximidate

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C([O-])=N[C@]([H])(C)C(O)=O

InChI Identifier

InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/p-3/t8-,9-,11-,12-,14-,15-,16-,17-,18-,20-,22?/m1/s1

InChI Key

NTMMCWJNQNKACG-JKXSCJIPSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose-5-phosphate
Pentose phosphate
N-acyl-alpha-hexosamine
N-acyl-alpha amino acid or derivatives
Alanine or derivatives
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Alpha-amino acid or derivatives
Monoalkyl phosphate
Pyrimidone
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Monosaccharide
Hydropyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	24.6 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-3.1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	374.77 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	183.2 m³·mol⁻¹	ChemAxon
Polarizability	63.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1000000900-cc136c40bfe040214696	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-1000000900-0dc72977176850c9b9ac	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9100000000-a416ded5b4e50cf91dfc	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0005-9000001700-a0bdb0b84c8d81da8c53	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006t-9000000600-d2346b1b2283668d5577	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003u-9300000000-ad0e45c2a367bc850008	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	626.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	457.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	259.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	359.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	328.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	200.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	853.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	589.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	383.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	159.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	266.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	176.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	67.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	559.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	478.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	74.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	336.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	835.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	696.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_1	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	1261.48
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_2	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2998.96
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_3	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	704.513
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_4	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2617.23
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_5	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	958.858
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_6	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2380.88
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_7	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	3227.4
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_8	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	3063.7
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_9	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	1903.75
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_10	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	1527.56
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_11	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2173.89
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_12	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2197.68
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_13	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2782.2
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_14	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	972.675
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_15	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2785.14
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_16	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1411.71
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_17	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	4154.27
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_18	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	865.122
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_19	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	1662.25
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_20	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	3467.3
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_21	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2854.27
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_22	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2236.94
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_23	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	666.085
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_24	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2268.59
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_25	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	2605.61
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_26	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	82.9827
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_27	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	3037.27
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_28	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard non polar	2025-10-24	1168.06
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_1	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2385.58
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_2	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2291.29
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_3	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2953.88
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_4	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1843.65
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_5	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1337.9
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_6	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1603.31
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_7	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2841.28
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_8	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1660.08
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_9	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2516.73
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_10	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1560.01
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_11	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2372.98
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_12	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1550.33
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_13	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	766.982
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_14	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	-128.074
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_15	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	884.622
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_16	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2556.91
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_17	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2259.5
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_18	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2877.54
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_19	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1865.61
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_20	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1349.95
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_21	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	2470.39
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_22	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	3151.81
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_23	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1681.51
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_24	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	3557.51
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_25	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O[Si](C)(C)C)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	1569.45
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_26	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1604.63
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_27	CC([O-])=N[C@H]1C(OP(=O)(O)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2663.57
Gas Chromatography	UDP-N-Acetylmuramyl-L-Ala_TMS_28	CC([O-])=N[C@H]1C(OP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]2O[C@@H](N3C=CC([O-])=NC3=O)[C@H](O)[C@@H]2O)O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C([O-])=N[C@H](C)C(=O)O	standard polar	2025-10-24	383.604

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
Peptidoglycan Biosynthesis		Escherichia coli Pseudomonas aeruginosa Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Pseudomonas aeruginosa PA7 Acinetobacter sp. ADP1 Actinobacillus succinogenes 130Z Escherichia coli CFT073 Myxococcus xanthus DK 1622 Ochrobactrum anthropi Bacillus subtilis Pseudomonas stutzeri Klebsiella pneumoniae Bacillus cereus Pseudomonas fluorescens Pf-5 Salmonella enterica Haemophilus influenzae Haemophilus influenzae Rd KW20 Rhodospirillum rubrum ATCC 11170 Shewanella denitrificans OS217 Acinetobacter baumannii Bacillus cereus AH187 (F4810/72) Bacillus timonensis 10403023 Geobacter metallireducens Haemophilus parainfluenzae T3T1 Methylobacterium nodulans Ochrobactrum anthropi ATCC 49188 Ochrobactrum intermedium LMG 3301 Pelobacter carbinolicus Comamonas testosteroni Burkholderia cepacia Pseudomonas fluorescens Pseudomonas mendocina Pseudomonas putida Pseudomonas syringae Xanthomonas campestris Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Methylococcus capsulatus Citrobacter koseri Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Aeromonas hydrophila Cytophaga hutchinsonii Rhodopseudomonas palustris Bacillus licheniformis Priestia megaterium Bacillus thuringiensis Desulfobacterium autotrophicum Xylella fastidiosa Roseobacter denitrificans Pelobacter propionicus Stenotrophomonas maltophilia Brachyspira pilosicoli Burkholderia vietnamiensis Sodalis glossinidius Enterobacter cancerogenus Achromobacter xylosoxidans Burkholderia multivorans Burkholderia cenocepacia Syntrophobacter fumaroxidans Citrobacter youngae Burkholderia ambifaria Alicycliphilus denitrificans Shewanella denitrificans Methylocella silvestris Escherichia albertii Geobacter bemidjiensis Geobacter lovleyi Syntrophus aciditrophicus Agrobacterium tumefaciens Haemophilus parainfluenzae Klebsiella variicola Achromobacter xylosoxidans A8 Acinetobacter baumannii SDF Acinetobacter baumannii ACICU Acinetobacter baumannii AB0057 Acinetobacter baumannii AB307-0294 Actinobacillus pleuropneumoniae serovar 5b str. L20 Actinobacillus pleuropneumoniae serovar 3 str. JL03 Actinobacillus pleuropneumoniae serovar 7 str. AP76 Aeromonas hydrophila subsp. hydrophila ATCC 7966 Agrobacterium tumefaciens str. C58 Bacillus cereus ATCC 10987 Bacillus thuringiensis serovar konkukian str. 97-27 Bacillus amyloliquefaciens FZB42 Bacillus cereus B4264 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Priestia megaterium DSM 319 Bacillus subtilis subsp. spizizenii str. W23 Bacillus amyloliquefaciens DSM 7 Bradyrhizobium japonicum USDA 110 Citrobacter koseri ATCC BAA-895 Cronobacter sakazakii ATCC BAA-894 Delftia acidovorans SPH-1 Dyadobacter fermentans DSM 18053 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli APEC O1 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Haemophilus influenzae 86-028NP Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Escherichia coli 042 Acinetobacter calcoaceticus PHEA-2 Edwardsiella tarda FL6-60 Proteus mirabilis HI4320 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas stutzeri A1501 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Rhizobium leguminosarum bv. viciae 3841 Rhizobium leguminosarum bv. trifolii WSM2304 Rhodococcus erythropolis PR4 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella dysenteriae Sd197 Shigella flexneri 5 str. 8401 Spirosoma linguale DSM 74 Stenotrophomonas maltophilia K279a Stenotrophomonas maltophilia R551-3 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Bacteroides graminisolvens Bacteroides graminisolvens DSM 19988 = JCM 15093 Odoribacter laneus YIT 12061 Prevotella buccae ATCC 33574 Prevotella oralis ATCC 33269 Spirosoma linguale Thermodesulfovibrio yellowstonii Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Rhizobium etli Xanthobacter autotrophicus Alcaligenes faecalis Burkholderia cepacia GG4 Methyloversatilis universalis Methyloversatilis universalis FAM5 Desulfococcus oleovorans Bilophila wadsworthia 3_1_6 Aeromonas caviae Aeromonas media Aeromonas veronii Succinivibrio dextrinosolvens Allochromatium vinosum Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Enterobacter hormaechei Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Tatumella ptyseos Tatumella ptyseos ATCC 33301 Edwardsiella tarda Edwardsiella tarda ATCC 23685 Hafnia alvei Hafnia alvei ATCC 51873 Morganella morganii Morganella morganii subsp. morganii KT Providencia rustigianii DSM 4541 Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Plesiomonas shigelloides 302-73 Actinobacillus pleuropneumoniae Aggregatibacter aphrophilus Haemophilus haemolyticus Haemophilus sputorum Acinetobacter pittii Acinetobacter haemolyticus Acinetobacter johnsonii Acinetobacter johnsonii SH046 Acinetobacter junii SH205 Brachyspira pilosicoli B2904 Leptospira interrogans Brevibacterium casei Brevibacterium casei S18 Ralstonia eutropha H16 Xanthomonas campestris pv. campestris str. ATCC 33913 Xanthomonas campestris pv. campestris str. B100 Xanthomonas campestris pv. campestris str. 8004 Shewanella frigidimarina NCIMB 400 Bacillus cytotoxicus NVH 391-98 Lachnoclostridium phytofermentans ISDg Amycolatopsis mediterranei U32 Arthrobacter chlorophenolicus A6 Conexibacter woesei DSM 14684 Mycobacterium vanbaalenii PYR-1 Mycobacterium sp. Spyr1 Bacillus tusciae DSM 2912 Pseudonocardia dioxanivorans CB1190 Streptomyces violaceusniger Tu 4113 Streptosporangium roseum DSM 43021 Paraburkholderia graminis C4D1M Klebsiella aerogenes KCTC 2190 Acidobacterium capsulatum ATCC 51196 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Acidovorax ebreus TPSY Aeromonas salmonicida subsp. salmonicida A449 Agrobacterium vitis S4 Agrobacterium radiobacter K84 Rhodoferax ferrireducens T118 Alcanivorax borkumensis SK2 Alicycliphilus denitrificans K601 Anabaena variabilis ATCC 29413 Anaeromyxobacter dehalogenans 2CP-C Anaeromyxobacter sp. K Anaeromyxobacter dehalogenans 2CP-1 Azotobacter vinelandii DJ Mannheimia succiniciproducens MBEL55E Beijerinckia indica subsp. indica ATCC 9039 Bordetella avium 197N Brachyspira hyodysenteriae WA1 Brachyspira murdochii DSM 12563 Brachyspira pilosicoli 95/1000 Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Brucella melitensis bv. 1 str. 16M Brucella abortus bv. 1 str. 9-941 Brucella ovis ATCC 25840 Brucella canis ATCC 23365 Brucella suis ATCC 23445 Brucella abortus S19 Brucella melitensis ATCC 23457 Brucella microti CCM 4915 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia ambifaria AMMD Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Burkholderia vietnamiensis G4 Burkholderia cenocepacia MC0-3 Burkholderia ambifaria MC40-6 Burkholderia phymatum STM815 Burkholderia phytofirmans PsJN Burkholderia cenocepacia J2315 Candidatus Koribacter versatilis Ellin345 Caulobacter crescentus CB15 Caulobacter crescentus NA1000 Caulobacter segnis ATCC 21756 Cellvibrio japonicus Ueda107 Chitinophaga pinensis DSM 2588 Citrobacter rodentium ICC168 Colwellia psychrerythraea 34H Cronobacter turicensis z3032 Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Cytophaga hutchinsonii ATCC 33406 Desulfobacterium autotrophicum HRM2 Desulfococcus oleovorans Hxd3 Desulfomicrobium baculatum DSM 4028 Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Dinoroseobacter shibae DFL 12 Edwardsiella ictaluri 93-146 Enterobacter sp. 638 Enterobacter cloacae SCF1 Erwinia tasmaniensis Et1/99 Erwinia amylovora CFBP1430 Erwinia billingiae Eb661 Erythrobacter litoralis HTCC2594 Flavobacterium psychrophilum JIP02/86 Geobacter metallireducens GS-15 Geobacter uraniireducens Rf4 Geobacter lovleyi SZ Geobacter bemidjiensis Bem Geobacter sp. FRC-32 Geobacter sp. M18 Gramella forsetii KT0803 Granulibacter bethesdensis CGDNIH1 Haemophilus parasuis SH0165 Haemophilus influenzae F3047 Hahella chejuensis KCTC 2396 Haliangium ochraceum DSM 14365 Halothiobacillus neapolitanus c2 Herminiimonas arsenicoxydans Hyphomonas neptunium ATCC 15444 Jannaschia sp. CCS1 Janthinobacterium sp. Marseille Klebsiella pneumoniae 342 Leptospira borgpetersenii serovar Hardjo-bovis JB197 Leptothrix cholodnii SP-6 Magnetospirillum magneticum AMB-1 Marinobacter aquaeolei VT8 Marinomonas posidonica IVIA-Po-181 Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Methylobacterium extorquens AM1 Methylobacterium extorquens DM4 Methylocella silvestris BL2 Methylovorus glucosetrophus SIP3-4 Nitrobacter winogradskyi Nb-255 Nitrobacter hamburgensis X14 Nostoc sp. PCC 7120 Nostoc punctiforme PCC 73102 Novosphingobium aromaticivorans DSM 12444 Geobacter sulfurreducens PCA Xanthomonas axonopodis pv. citri str. 306 Leptospira interrogans serovar Lai str. 56601 Chromobacterium violaceum ATCC 12472 Bdellovibrio bacteriovorus HD100 Leptospira interrogans serovar Copenhageni str. Fiocruz L1-130 Sodalis glossinidius str. 'morsitans' Sorangium cellulosum 'So ce 56' Leptospira biflexa serovar Patoc strain 'Patoc 1 (Paris)' Thermodesulfovibrio yellowstonii DSM 11347 Rhodobacter capsulatus SB1003 Pantoea ananatis LMG 20103 Paracoccus denitrificans PD1222 Parvibaculum lavamentivorans DS-1 Pasteurella multocida subsp. multocida str. Pm70 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Pedobacter heparinus DSM 2366 Pelobacter carbinolicus DSM 2380 Pelobacter propionicus DSM 2379 Phenylobacterium zucineum HLK1 Photobacterium profundum SS9 Photorhabdus luminescens subsp. laumondii TTO1 Photorhabdus asymbiotica subsp. asymbiotica ATCC 43949 Polaromonas sp. JS666 Polaromonas naphthalenivorans CJ2 Pseudomonas syringae pv. tomato str. DC3000 Pseudomonas syringae pv. phaseolicola 1448A Pseudomonas syringae pv. syringae B728a Pseudomonas entomophila L48 Pseudomonas fulva 12-X Psychrobacter arcticus 273-4 Psychrobacter cryohalolentis K5 Rhizobium etli CFN 42 Rhizobium etli CIAT 652 Rhizobium leguminosarum bv. trifolii WSM1325 Rhodopseudomonas palustris CGA009 Rhodopseudomonas palustris HaA2 Rhodopseudomonas palustris BisB5 Rhodospirillum centenum SW Roseobacter denitrificans OCh 114 Roseobacter litoralis Och 149 Ruegeria pomeroyi DSS-3 Ruegeria sp. TM1040 Saccharophagus degradans 2-40 Salmonella enterica subsp. enterica serovar Paratyphi A str. Shewanella oneidensis MR-1 Shewanella sp. ANA-3 Shewanella amazonensis SB2B Shewanella sp. W3-18-1 Shewanella baltica OS155 Shewanella baltica OS195 Shigella flexneri 2a str. 301 Shigella boydii Sb227 Shigella boydii CDC 3083-94 Sinorhizobium meliloti 1021 Sinorhizobium medicae WSM419 Sphingobium japonicum UT26S Sphingomonas wittichii RW1 Sphingopyxis alaskensis RB2256 Syntrophobacter fumaroxidans MPOB Syntrophus aciditrophicus SB Tolumonas auensis DSM 9187 Variovorax paradoxus EPS Xanthobacter autotrophicus Py2 Xanthomonas campestris pv. vesicatoria str. 85-10 Xenorhabdus bovienii SS-2004 Xenorhabdus nematophila ATCC 19061 Xylella fastidiosa 9a5c Xylella fastidiosa Temecula1 Xylella fastidiosa M23 Zymomonas mobilis subsp. pomaceae ATCC 29192 Atlantibacter hermannii NBRC 105704 Klebsiella michiganensis KCTC 1686 Chania multitudinisentens RB-25

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019287	D-Glutamic acid	UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate	UDP-N-acetylmuramoylalanine--D-glutamate ligase	Ligation	PathBank	31602464
MMDBr0019288	L-Alanine	UDP-N-Acetylmuramyl-L-Ala	UDP-N-acetylmuramate--L-alanine ligase	Ligation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25246252

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for UDP-N-Acetylmuramyl-L-Ala (MMDBc0030160)

MOL for #<Metabolite:0x00007f2e3b975930>

3D MOL for #<Metabolite:0x00007f2e3b975930>

3D SDF for #<Metabolite:0x00007f2e3b975930>

3D-SDF for #<Metabolite:0x00007f2e3b975930>

PDB for #<Metabolite:0x00007f2e3b975930>

3D PDB for #<Metabolite:0x00007f2e3b975930>

SMILES for #<Metabolite:0x00007f2e3b975930>

INCHI for #<Metabolite:0x00007f2e3b975930>

Structure for #<Metabolite:0x00007f2e3b975930>

3D Structure for #<Metabolite:0x00007f2e3b975930>