Showing metabocard for 3-Carboxy-1-hydroxypropylthiamine diphosphate (MMDBc0047954)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:18:41 UTC
Update Date2024-04-30 20:33:41 UTC
Metabolite IDMMDBc0047954
Metabolite Identification
Common Name3-Carboxy-1-hydroxypropylthiamine diphosphate
Description3-Carboxy-1-hydroxypropyl-ThPP is an intermediate in Citrate cycle (TCA cycle). 3-Carboxy-1-hydroxypropyl-ThPP is the second to last step in the synthesis of Succinyl-CoA and is converted from 2-Oxoglutarate via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2). It is then converted to S-Succinyldihydrolipoamide-E via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f925806ff08>

 
  Mrv0541 02231220502D          
 
 33 34  0  0  0  0            999 V2000
   22.8196   -6.5262    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   23.1983   -5.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4013   -7.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -6.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0107   -5.9272    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8264   -5.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1347   -6.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3083   -7.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0072   -5.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2809   -4.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8679   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -6.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5599   -6.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -7.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -7.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -6.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2931   -7.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -6.6020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.2462   -7.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7183   -6.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1950   -7.4695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -6.5331    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1401   -6.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6203   -7.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -5.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -5.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6354   -4.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8049   -4.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3511   -4.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4365   -3.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5  7  1  0  0  0  0
 18 20  1  0  0  0  0
 21 28  2  0  0  0  0
 25 29  2  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  CHG  1   1   1
M  END
Download

3D MOL for #<Metabolite:0x00007f925806ff08>

HMDB0006744
     RDKit          3D
3-Carboxy-1-hydroxypropylthiamine diphosphate
 58 59  0  0  0  0  0  0  0  0999 V2000
   -5.3754    4.8155   -2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6009    3.5319   -2.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    3.1781   -2.8146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.0337   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.1418   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396   -0.0639   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0125   -0.4826 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4421   -0.4002    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -1.0411    1.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695   -0.1488    2.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -2.2394    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -3.2414    1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863   -3.8932    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -3.6514    0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127   -4.8160   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -0.1335    1.4974 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807    0.4734    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9197   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362    0.2455    1.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6546    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -0.0089    2.0775 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0590    0.5826    3.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333   -1.6756    2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.5044    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8158   -0.4398    0.6134 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9184   -0.7168   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2083    0.3382    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016   -1.9366    1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    0.4408   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.8797   -2.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2646    1.5303   -0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.7808    0.2914 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    2.7091   -1.0217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0386    4.6130   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653    5.6073   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327    5.0731   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    1.8165   -3.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -0.4124   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -0.9178   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -1.4362    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    0.3114    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.8755    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -2.7527    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -4.0567    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -2.8675    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462   -5.7027   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5837   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9955    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -0.8502    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    0.5166    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7854   -2.0068    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518    0.6589   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5473    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    0.2682   -3.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    1.9685   -2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.6942   -2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981   -0.1904    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    1.1682    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 17 29  2  0
 29 30  1  0
  5 31  1  0
 31 32  1  0
 31 33  2  0
 33  2  1  0
 29  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 23 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
M  CHG  1   7   1
M  END
Download

3D SDF for #<Metabolite:0x00007f925806ff08>

 
  Mrv0541 02231220502D          
 
 33 34  0  0  0  0            999 V2000
   22.8196   -6.5262    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   23.1983   -5.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4013   -7.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -6.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0107   -5.9272    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8264   -5.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1347   -6.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3083   -7.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0072   -5.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2809   -4.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8679   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -6.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5599   -6.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -7.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -7.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -6.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2931   -7.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -6.6020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.2462   -7.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7183   -6.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1950   -7.4695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -6.5331    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1401   -6.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6203   -7.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -5.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -5.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6354   -4.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8049   -4.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3511   -4.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4365   -3.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5  7  1  0  0  0  0
 18 20  1  0  0  0  0
 21 28  2  0  0  0  0
 25 29  2  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
MMDBc0047954

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC(C(O)CCC(O)=O)=[N+]1CC1=C(N)N=C(C)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N4O10P2S/c1-9-13(5-6-29-32(27,28)30-31(24,25)26)33-16(12(21)3-4-14(22)23)20(9)8-11-7-18-10(2)19-15(11)17/h7,12,21H,3-6,8H2,1-2H3,(H5-,17,18,19,22,23,24,25,26,27,28)/p+1

> <INCHI_KEY>
ZWUKRGPVMMTMAF-UHFFFAOYSA-O

> <FORMULA>
C16H25N4O10P2S

> <MOLECULAR_WEIGHT>
527.403

> <EXACT_MASS>
527.076661754

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
47.108163008895595

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-7.2914789016294765

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.099590167678406

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.773930796829486

> <JCHEM_PKA_STRONGEST_BASIC>
5.538537381625124

> <JCHEM_POLAR_SURFACE_AREA>
226.49999999999997

> <JCHEM_REFRACTIVITY>
127.36989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carboxy-1-hydroxypropyl-thpp

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f925806ff08>

HMDB0006744
     RDKit          3D
3-Carboxy-1-hydroxypropylthiamine diphosphate
 58 59  0  0  0  0  0  0  0  0999 V2000
   -5.3754    4.8155   -2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6009    3.5319   -2.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    3.1781   -2.8146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.0337   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.1418   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396   -0.0639   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0125   -0.4826 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4421   -0.4002    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -1.0411    1.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695   -0.1488    2.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -2.2394    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -3.2414    1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863   -3.8932    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -3.6514    0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127   -4.8160   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -0.1335    1.4974 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807    0.4734    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9197   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362    0.2455    1.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6546    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -0.0089    2.0775 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0590    0.5826    3.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333   -1.6756    2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.5044    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8158   -0.4398    0.6134 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9184   -0.7168   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2083    0.3382    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016   -1.9366    1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    0.4408   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.8797   -2.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2646    1.5303   -0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.7808    0.2914 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    2.7091   -1.0217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0386    4.6130   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653    5.6073   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327    5.0731   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    1.8165   -3.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -0.4124   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -0.9178   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -1.4362    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    0.3114    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.8755    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -2.7527    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -4.0567    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -2.8675    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462   -5.7027   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5837   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9955    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -0.8502    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    0.5166    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7854   -2.0068    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518    0.6589   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5473    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    0.2682   -3.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    1.9685   -2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.6942   -2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981   -0.1904    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    1.1682    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 17 29  2  0
 29 30  1  0
  5 31  1  0
 31 32  1  0
 31 33  2  0
 33  2  1  0
 29  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 23 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
M  CHG  1   7   1
M  END
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PDB for #<Metabolite:0x00007f925806ff08>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      42.597 -12.182   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      43.303 -10.814   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      43.682 -13.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      41.260 -11.418   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      44.820 -11.064   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      42.609  -9.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      45.051 -12.581   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.509 -14.798   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.930 -12.189   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.080  -9.349   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      43.458  -8.153   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      46.420 -13.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.930 -13.737   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.580 -11.424   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.712 -12.452   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      38.580 -14.528   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      41.260 -14.508   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      37.256 -12.189   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      49.080 -13.159   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      37.256 -13.737   0.000  0.00  0.00           C+0
HETATM   21  P   UNK     0      50.372 -12.324   0.000  0.00  0.00           P+0
HETATM   22  C   UNK     0      35.926 -14.508   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      51.741 -13.031   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      50.764 -13.943   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      53.033 -12.195   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      54.395 -12.896   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      53.425 -13.814   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      50.372 -10.784   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      53.033 -10.655   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      40.386  -7.965   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.836  -7.874   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      37.989  -9.160   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      38.148  -6.502   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2    7                                                       
CONECT    6    2   10   11                                                  
CONECT    7    3   12    5                                                  
CONECT    8    3                                                            
CONECT    9    4   13   14                                                  
CONECT   10    6   30                                                       
CONECT   11    6                                                            
CONECT   12    7   15                                                       
CONECT   13    9   16   17                                                  
CONECT   14    9   18                                                       
CONECT   15   12   19                                                       
CONECT   16   13   20                                                       
CONECT   17   13                                                            
CONECT   18   14   20                                                       
CONECT   19   15   21                                                       
CONECT   20   16   22   18                                                  
CONECT   21   19   23   24   28                                             
CONECT   22   20                                                            
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21                                                            
CONECT   29   25                                                            
CONECT   30   10   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END
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3D PDB for #<Metabolite:0x00007f925806ff08>

COMPND    HMDB0006744
HETATM    1  C1  UNL     1      -5.375   4.815  -2.209  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.601   3.532  -2.016  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.594   3.178  -2.815  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.919   2.034  -2.632  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.231   1.142  -1.588  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.440  -0.064  -1.443  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.302  -0.012  -0.483  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -1.442  -0.400   0.773  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.564  -1.041   1.543  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.869  -0.149   2.571  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.944  -2.239   2.298  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.314  -3.241   1.408  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.186  -3.893   0.435  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.402  -3.651   0.355  1.00  0.00           O  
HETATM   15  O3  UNL     1      -1.613  -4.816  -0.426  1.00  0.00           O  
HETATM   16  S1  UNL     1       0.113  -0.133   1.497  1.00  0.00           S  
HETATM   17  C11 UNL     1       0.881   0.473   0.103  1.00  0.00           C  
HETATM   18  C12 UNL     1       2.327   0.920  -0.038  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.136   0.246   1.061  1.00  0.00           C  
HETATM   20  O4  UNL     1       4.452   0.655   0.913  1.00  0.00           O  
HETATM   21  P1  UNL     1       5.463  -0.009   2.077  1.00  0.00           P  
HETATM   22  O5  UNL     1       5.059   0.583   3.428  1.00  0.00           O  
HETATM   23  O6  UNL     1       5.433  -1.676   2.122  1.00  0.00           O  
HETATM   24  O7  UNL     1       7.050   0.504   1.788  1.00  0.00           O  
HETATM   25  P2  UNL     1       7.816  -0.440   0.613  1.00  0.00           P  
HETATM   26  O8  UNL     1       6.918  -0.717  -0.571  1.00  0.00           O  
HETATM   27  O9  UNL     1       9.208   0.338   0.070  1.00  0.00           O  
HETATM   28  O10 UNL     1       8.302  -1.937   1.244  1.00  0.00           O  
HETATM   29  C14 UNL     1      -0.103   0.441  -0.850  1.00  0.00           C  
HETATM   30  C15 UNL     1       0.238   0.880  -2.262  1.00  0.00           C  
HETATM   31  C16 UNL     1      -4.265   1.530  -0.791  1.00  0.00           C  
HETATM   32  N3  UNL     1      -4.807   0.781   0.291  1.00  0.00           N  
HETATM   33  N4  UNL     1      -4.921   2.709  -1.022  1.00  0.00           N  
HETATM   34  H1  UNL     1      -6.039   4.613  -3.087  1.00  0.00           H  
HETATM   35  H2  UNL     1      -4.665   5.607  -2.537  1.00  0.00           H  
HETATM   36  H3  UNL     1      -5.933   5.073  -1.296  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.119   1.816  -3.351  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.084  -0.412  -2.451  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.118  -0.918  -1.134  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.360  -1.436   0.965  1.00  0.00           H  
HETATM   41  H8  UNL     1      -2.047   0.311   2.831  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.197  -1.875   3.028  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.736  -2.753   2.888  1.00  0.00           H  
HETATM   44  H11 UNL     1      -0.918  -4.057   2.086  1.00  0.00           H  
HETATM   45  H12 UNL     1      -0.375  -2.867   0.913  1.00  0.00           H  
HETATM   46  H13 UNL     1      -2.046  -5.703  -0.595  1.00  0.00           H  
HETATM   47  H14 UNL     1       2.645   0.584  -1.037  1.00  0.00           H  
HETATM   48  H15 UNL     1       2.324   1.996   0.012  1.00  0.00           H  
HETATM   49  H16 UNL     1       3.087  -0.850   0.867  1.00  0.00           H  
HETATM   50  H17 UNL     1       2.678   0.517   2.021  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.785  -2.007   1.242  1.00  0.00           H  
HETATM   52  H19 UNL     1       9.052   0.659  -0.836  1.00  0.00           H  
HETATM   53  H20 UNL     1       8.543  -2.547   0.511  1.00  0.00           H  
HETATM   54  H21 UNL     1      -0.312   0.268  -3.013  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.070   1.968  -2.375  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.301   0.694  -2.503  1.00  0.00           H  
HETATM   57  H24 UNL     1      -5.198  -0.190   0.152  1.00  0.00           H  
HETATM   58  H25 UNL     1      -4.845   1.168   1.255  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   33
CONECT    3    4
CONECT    4    5    5   37
CONECT    5    6   31
CONECT    6    7   38   39
CONECT    7    8    8   29
CONECT    8    9   16
CONECT    9   10   11   40
CONECT   10   41
CONECT   11   12   42   43
CONECT   12   13   44   45
CONECT   13   14   14   15
CONECT   15   46
CONECT   16   17
CONECT   17   18   29   29
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21
CONECT   21   22   22   23   24
CONECT   23   51
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   52
CONECT   28   53
CONECT   29   30
CONECT   30   54   55   56
CONECT   31   32   33   33
CONECT   32   57   58
END
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SMILES for #<Metabolite:0x00007f925806ff08>

CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC(C(O)CCC(O)=O)=[N+]1CC1=C(N)N=C(C)N=C1
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INCHI for #<Metabolite:0x00007f925806ff08>

InChI=1S/C16H24N4O10P2S/c1-9-13(5-6-29-32(27,28)30-31(24,25)26)33-16(12(21)3-4-14(22)23)20(9)8-11-7-18-10(2)19-15(11)17/h7,12,21H,3-6,8H2,1-2H3,(H5-,17,18,19,22,23,24,25,26,27,28)/p+1
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Synonyms
ValueSource
2-(3-Carboxy-1-hydroxypropyl)thiamine diphosphateChEBI
3-Carboxy-1-hydroxypropyl-THPPChEBI
Succinate semialdehyde-thiamin diphosphateKegg
2-(3-Carboxy-1-hydroxypropyl)thiamine diphosphoric acidGenerator
Succinic acid semialdehyde-thiamin diphosphoric acidGenerator
3-Carboxy-1-hydroxypropylthiamine diphosphoric acidGenerator
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-diphosphoethyl)-4-methyl-1,3-thiazol-3-iumHMDB
Molecular FormulaC16H25N4O10P2S
Average Mass527.403
Monoisotopic Mass527.076661754
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
Traditional Name3-carboxy-1-hydroxypropyl-thpp
CAS Registry NumberNot Available
SMILES
CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC(C(O)CCC(O)=O)=[N+]1CC1=C(N)N=C(C)N=C1
InChI Identifier
InChI=1S/C16H24N4O10P2S/c1-9-13(5-6-29-32(27,28)30-31(24,25)26)33-16(12(21)3-4-14(22)23)20(9)8-11-7-18-10(2)19-15(11)17/h7,12,21H,3-6,8H2,1-2H3,(H5-,17,18,19,22,23,24,25,26,27,28)/p+1
InChI KeyZWUKRGPVMMTMAF-UHFFFAOYSA-O