MiMeDB: Showing metabocard for SAICAR (MMDBc0029510)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:15 UTC

Update Date

2024-04-30 19:36:36 UTC

Metabolite ID

MMDBc0029510

Metabolite Identification

Common Name

SAICAR

Description

SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. (Wikipedia )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000132D          

 30 31  0  0  0  0            999 V2000
10000.2775 9999.2142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.678610000.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.392610000.5447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.108710000.1320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.822710000.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.538710000.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.252710000.5447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.5387 9999.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1087 9999.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8227 9998.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.3926 9998.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.6786 9999.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1147 9998.6834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3238 9998.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.856610000.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.141610000.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.426410000.5447    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9995.838210001.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.707210000.1300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.012610001.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.237310000.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.569910000.1410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8248 9999.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.6498 9999.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.904710000.1410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.295910000.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.628510000.5355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.883410001.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.708410001.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.963310000.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 26 30  2  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30  2  1  0  0  0  0
  1 26  1  0  0  0  0
 24 13  1  6  0  0  0
 23 14  1  6  0  0  0
 22 15  1  1  0  0  0
 25 27  1  1  0  0  0
M  END

HMDB0000797
     RDKit          3D
SAICAR
 49 50  0  0  0  0  0  0  0  0999 V2000
   -0.0430    1.3881    0.5192 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    0.1791   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -0.1213   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    0.6980    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    1.8242    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486    0.2422    0.0139 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.0610    0.3959 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1502    0.3863    1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6147   -0.9150    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420   -1.9055    0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9283   -1.0787    0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2231    1.2959   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9310    0.8144   -1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3726    2.0595   -0.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038   -1.3499   -0.7315 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.7731   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -0.8245   -0.4996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245   -0.9010   -0.5425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3786    0.2821   -0.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -0.1353   -0.3370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6807    0.7926    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620    0.2830    0.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1092    1.2641    0.8920 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.3799    1.2901    0.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5177    2.8544    1.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5415    0.6922    2.4217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7995   -1.4896    0.2976 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2963   -2.4001   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -1.8454    0.4850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0757   -3.1764    0.1587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022    1.5361    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    2.1330   -0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046   -0.6902   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699    2.0097    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9729    1.0600    1.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    0.2109    2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1971   -0.9347   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3175    2.9823   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038   -2.7234   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319   -1.2222   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.1369   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4985    0.7474    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6026    1.8405    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3266    3.1860    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3270    0.0902    2.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507   -1.5233    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -2.7880   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -1.5517    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -3.7172    0.8490 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 20 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 17  2  1  0
 29 18  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
 11 37  1  0
 14 38  1  0
 16 39  1  0
 18 40  1  6
 20 41  1  6
 21 42  1  0
 21 43  1  0
 25 44  1  0
 26 45  1  0
 27 46  1  1
 28 47  1  0
 29 48  1  1
 30 49  1  0
M  END


  Mrv1652309042000132D          

 30 31  0  0  0  0            999 V2000
10000.2775 9999.2142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.678610000.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.392610000.5447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.108710000.1320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.822710000.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.538710000.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.252710000.5447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.5387 9999.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1087 9999.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8227 9998.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.3926 9998.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.6786 9999.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1147 9998.6834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3238 9998.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.856610000.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.141610000.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.426410000.5447    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9995.838210001.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.707210000.1300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.012610001.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.237310000.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.569910000.1410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8248 9999.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.6498 9999.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.904710000.1410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.295910000.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.628510000.5355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.883410001.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.708410001.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.963310000.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 26 30  2  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30  2  1  0  0  0  0
  1 26  1  0  0  0  0
 24 13  1  6  0  0  0
 23 14  1  6  0  0  0
 22 15  1  1  0  0  0
 25 27  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029510

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1

> <INCHI_KEY>
NAQGHJTUZRHGAC-ZZZDFHIKSA-N

> <FORMULA>
C13H19N4O12P

> <MOLECULAR_WEIGHT>
454.2833

> <EXACT_MASS>
454.073708604

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.50191613972262

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-4.825361675843606

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.997173380015799

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2173138245476895

> <JCHEM_PKA_STRONGEST_BASIC>
4.543300932982183

> <JCHEM_POLAR_SURFACE_AREA>
263.98999999999995

> <JCHEM_REFRACTIVITY>
90.65269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saicar

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000797
     RDKit          3D
SAICAR
 49 50  0  0  0  0  0  0  0  0999 V2000
   -0.0430    1.3881    0.5192 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    0.1791   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -0.1213   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    0.6980    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    1.8242    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486    0.2422    0.0139 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.0610    0.3959 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1502    0.3863    1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6147   -0.9150    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420   -1.9055    0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9283   -1.0787    0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2231    1.2959   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9310    0.8144   -1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3726    2.0595   -0.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038   -1.3499   -0.7315 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.7731   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -0.8245   -0.4996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245   -0.9010   -0.5425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3786    0.2821   -0.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -0.1353   -0.3370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6807    0.7926    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620    0.2830    0.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1092    1.2641    0.8920 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.3799    1.2901    0.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5177    2.8544    1.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5415    0.6922    2.4217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7995   -1.4896    0.2976 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2963   -2.4001   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -1.8454    0.4850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0757   -3.1764    0.1587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022    1.5361    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    2.1330   -0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046   -0.6902   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699    2.0097    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9729    1.0600    1.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    0.2109    2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1971   -0.9347   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3175    2.9823   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038   -2.7234   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319   -1.2222   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.1369   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4985    0.7474    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6026    1.8405    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3266    3.1860    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3270    0.0902    2.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507   -1.5233    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -2.7880   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -1.5517    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -3.7172    0.8490 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 20 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 17  2  1  0
 29 18  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
 11 37  1  0
 14 38  1  0
 16 39  1  0
 18 40  1  6
 20 41  1  6
 21 42  1  0
 21 43  1  0
 25 44  1  0
 26 45  1  0
 27 46  1  1
 28 47  1  0
 29 48  1  1
 30 49  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0    8667.1858665.200   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8669.8008666.913   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8671.1338667.683   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8672.4708666.913   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8673.8028667.683   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8675.1398666.913   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8676.4728667.683   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8675.1398665.372   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8672.4708665.372   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8673.8028664.599   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8671.1338664.599   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8669.8008665.372   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8665.0148664.209   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8661.6718664.225   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8660.7998667.683   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8659.4648666.913   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0    8658.1298667.683   0.000  0.00  0.00           P+0
HETATM   18  O   UNK     0    8658.8988669.020   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8656.7878666.909   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8657.3578669.020   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8663.3768667.835   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8662.1308666.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8662.6068665.465   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8664.1468665.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8664.6228666.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.2198666.761   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0    8665.9738667.666   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0    8666.4498669.131   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0    8667.9898669.131   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0    8668.4658667.666   0.000  0.00  0.00           C+0
CONECT    1   26                                                            
CONECT    2    3   12   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2                                                            
CONECT   13   24                                                            
CONECT   14   23                                                            
CONECT   15   16   22                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   22   25                                                       
CONECT   22   23   21   15                                                  
CONECT   23   22   24   14                                                  
CONECT   24   23   25   13                                                  
CONECT   25   24   21   27                                                  
CONECT   26   30   27    1                                                  
CONECT   27   26   28   25                                                  
CONECT   28   29   27                                                       
CONECT   29   28   30                                                       
CONECT   30   26   29    2                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0000797
HETATM    1  N1  UNL     1      -0.043   1.388   0.519  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.445   0.179  -0.034  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.791  -0.121  -0.166  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.936   0.698   0.217  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.723   1.824   0.734  1.00  0.00           O  
HETATM    6  N2  UNL     1       4.249   0.242   0.014  1.00  0.00           N  
HETATM    7  C4  UNL     1       5.371   1.061   0.396  1.00  0.00           C  
HETATM    8  C5  UNL     1       6.150   0.386   1.530  1.00  0.00           C  
HETATM    9  C6  UNL     1       6.615  -0.915   1.022  1.00  0.00           C  
HETATM   10  O2  UNL     1       5.842  -1.906   0.990  1.00  0.00           O  
HETATM   11  O3  UNL     1       7.928  -1.079   0.563  1.00  0.00           O  
HETATM   12  C7  UNL     1       6.223   1.296  -0.772  1.00  0.00           C  
HETATM   13  O4  UNL     1       5.931   0.814  -1.891  1.00  0.00           O  
HETATM   14  O5  UNL     1       7.373   2.059  -0.655  1.00  0.00           O  
HETATM   15  N3  UNL     1       1.804  -1.350  -0.731  1.00  0.00           N  
HETATM   16  C8  UNL     1       0.539  -1.773  -0.932  1.00  0.00           C  
HETATM   17  N4  UNL     1      -0.308  -0.825  -0.500  1.00  0.00           N  
HETATM   18  C9  UNL     1      -1.724  -0.901  -0.542  1.00  0.00           C  
HETATM   19  O6  UNL     1      -2.379   0.282  -0.218  1.00  0.00           O  
HETATM   20  C10 UNL     1      -3.716  -0.135  -0.337  1.00  0.00           C  
HETATM   21  C11 UNL     1      -4.681   0.793   0.345  1.00  0.00           C  
HETATM   22  O7  UNL     1      -5.962   0.283   0.160  1.00  0.00           O  
HETATM   23  P1  UNL     1      -7.109   1.264   0.892  1.00  0.00           P  
HETATM   24  O8  UNL     1      -8.380   1.290   0.049  1.00  0.00           O  
HETATM   25  O9  UNL     1      -6.518   2.854   1.017  1.00  0.00           O  
HETATM   26  O10 UNL     1      -7.541   0.692   2.422  1.00  0.00           O  
HETATM   27  C12 UNL     1      -3.800  -1.490   0.298  1.00  0.00           C  
HETATM   28  O11 UNL     1      -4.296  -2.400  -0.649  1.00  0.00           O  
HETATM   29  C13 UNL     1      -2.323  -1.845   0.485  1.00  0.00           C  
HETATM   30  O12 UNL     1      -2.076  -3.176   0.159  1.00  0.00           O  
HETATM   31  H1  UNL     1       0.102   1.536   1.545  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.531   2.133  -0.013  1.00  0.00           H  
HETATM   33  H3  UNL     1       4.405  -0.690  -0.414  1.00  0.00           H  
HETATM   34  H4  UNL     1       4.970   2.010   0.824  1.00  0.00           H  
HETATM   35  H5  UNL     1       6.973   1.060   1.821  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.445   0.211   2.371  1.00  0.00           H  
HETATM   37  H7  UNL     1       8.197  -0.935  -0.399  1.00  0.00           H  
HETATM   38  H8  UNL     1       7.317   2.982  -0.255  1.00  0.00           H  
HETATM   39  H9  UNL     1       0.304  -2.723  -1.370  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.132  -1.222  -1.528  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.969  -0.137  -1.424  1.00  0.00           H  
HETATM   42  H12 UNL     1      -4.499   0.747   1.458  1.00  0.00           H  
HETATM   43  H13 UNL     1      -4.603   1.841   0.009  1.00  0.00           H  
HETATM   44  H14 UNL     1      -6.327   3.186   0.105  1.00  0.00           H  
HETATM   45  H15 UNL     1      -8.327   0.090   2.321  1.00  0.00           H  
HETATM   46  H16 UNL     1      -4.351  -1.523   1.244  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.570  -2.788  -1.187  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.938  -1.552   1.463  1.00  0.00           H  
HETATM   49  H19 UNL     1      -2.532  -3.717   0.849  1.00  0.00           H  
CONECT    1    2   31   32
CONECT    2    3    3   17
CONECT    3    4   15
CONECT    4    5    5    6
CONECT    6    7   33
CONECT    7    8   12   34
CONECT    8    9   35   36
CONECT    9   10   10   11
CONECT   11   37
CONECT   12   13   13   14
CONECT   14   38
CONECT   15   16   16
CONECT   16   17   39
CONECT   17   18
CONECT   18   19   29   40
CONECT   19   20
CONECT   20   21   27   41
CONECT   21   22   42   43
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   25   44
CONECT   26   45
CONECT   27   28   29   46
CONECT   28   47
CONECT   29   30   48
CONECT   30   49
END

HMDB0000797
     RDKit          3D
SAICAR
 49 50  0  0  0  0  0  0  0  0999 V2000
   -0.0430    1.3881    0.5192 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    0.1791   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -0.1213   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    0.6980    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    1.8242    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486    0.2422    0.0139 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.0610    0.3959 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1502    0.3863    1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6147   -0.9150    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420   -1.9055    0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9283   -1.0787    0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2231    1.2959   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9310    0.8144   -1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3726    2.0595   -0.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038   -1.3499   -0.7315 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.7731   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -0.8245   -0.4996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245   -0.9010   -0.5425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3786    0.2821   -0.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -0.1353   -0.3370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6807    0.7926    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620    0.2830    0.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1092    1.2641    0.8920 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.3799    1.2901    0.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5177    2.8544    1.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5415    0.6922    2.4217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7995   -1.4896    0.2976 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2963   -2.4001   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -1.8454    0.4850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0757   -3.1764    0.1587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022    1.5361    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    2.1330   -0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046   -0.6902   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699    2.0097    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9729    1.0600    1.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    0.2109    2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1971   -0.9347   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3175    2.9823   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038   -2.7234   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319   -1.2222   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.1369   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4985    0.7474    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6026    1.8405    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3266    3.1860    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3270    0.0902    2.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507   -1.5233    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -2.7880   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -1.5517    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -3.7172    0.8490 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 20 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 17  2  1  0
 29 18  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
 11 37  1  0
 14 38  1  0
 16 39  1  0
 18 40  1  6
 20 41  1  6
 21 42  1  0
 21 43  1  0
 25 44  1  0
 26 45  1  0
 27 46  1  1
 28 47  1  0
 29 48  1  1
 30 49  1  0
M  END

Synonyms

Value	Source
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid	ChEBI
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate	ChEBI
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole	ChEBI
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole	ChEBI
Succino-aicar	ChEBI
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate	ChEBI
Succinylaminoimidazolecarboxamide ribose-5'-phosphate	ChEBI
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid	Generator
Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acid	Generator
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate	HMDB
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid	HMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate	HMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid	HMDB
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate	HMDB
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	HMDB
5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole	HMDB
5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide	HMDB
L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)	HMDB
L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)	HMDB
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate	HMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate	HMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid	HMDB
Phosphoribosylaminoimidazolesuccinocarboxamide	HMDB
N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate	HMDB
5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole	HMDB
SAICAR, (D)-isomer	HMDB
SAICAribotide	HMDB
Succinylaminoimidazole carboxamide ribotide	HMDB
SAICA ribotide	HMDB
Succinylaminoimidazolecarboxamide ribose-5’-phosphate	HMDB

Molecular Formula

C₁₃H₁₉N₄O₁₂P

Average Mass

454.2833

Monoisotopic Mass

454.073708604

IUPAC Name

(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid

Traditional Name

saicar

CAS Registry Number

3031-95-6

SMILES

NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1

InChI Key

NAQGHJTUZRHGAC-ZZZDFHIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

1-ribosyl-imidazolecarboxamides

Direct Parent

1-ribosyl-imidazolecarboxamides

Alternative Parents

Substituents

1-ribosyl-imidazolecarboxamide
Pentose-5-phosphate
Pentose phosphate
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Alpha-amino acid or derivatives
Pentose monosaccharide
2-heteroaryl carboxamide
Imidazolyl carboxylic acid derivative
Imidazole-4-carbonyl group
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Dicarboxylic acid or derivatives
Phosphoric acid ester
Aminoimidazole
Monosaccharide
Imidazole
Heteroaromatic compound
Azole
Vinylogous amide
Tetrahydrofuran
Amino acid or derivatives
Carboxamide group
Amino acid
1,2-diol
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazolecarboxamide (CHEBI:18319 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.73 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-4.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	263.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.65 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Fibroblasts
Intestine
Urine

Tissue Locations

Fibroblasts
Intestine

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192229	Adenylosuccinate lyase	Enzyme	P30566	Homo sapiens
MMDBp0192512	Multifunctional protein ADE2	Enzyme	P22234	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018512	L-Aspartic acid	SAICAR	Phosphoribosylaminoimidazole-succinocarboxamide synthase	Synthesis	PathBank	31602464
MMDBr0018513	SAICAR	Fumaric acid	Adenylosuccinate lyase	Non-hydrolytic bond cleavage (or its reversal)	PathBank	31602464
MMDBr0019842	L-Aspartic acid	SAICAR	Unknown Protein		PathBank	31602464
MMDBr0019843	SAICAR	Fumaric acid	Unknown Protein		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Adenylosuccinate lyase deficiency		Association	Human Cerebrospinal Fluid (CSF)	HMDB	15571235
Fumarase deficiency		Association	Human Urine	HMDB	24182348

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	8	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	362	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	174	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	113	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	28	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	921.0	0.0	1842.0	uM	Adult (>18 years old)	Not Specified	Adenylosuccinate lyase deficiency	HMDB	15571235
Human Urine	Detected and Quantified	<0.300			umol/mmol creatinine	Infant (0-1 year old)	Male	Fumarase deficiency	HMDB	24182348
Human Cerebrospinal fluid (csf)	Detected and Quantified	0			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15114530
Human Urine	Detected and Quantified	<1			umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	24182348
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified								HMDB

External Links

HMDB ID

HMDB0000797

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022251

KNApSAcK ID

Not Available

Chemspider ID

141175

KEGG Compound ID

C04823

BioCyc ID

P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

BiGG ID

44624

Wikipedia Link

Phosphoribosylaminoimidazolesuccinocarboxamide

METLIN ID

5762

PubChem Compound

160666

PDB ID

Not Available

ChEBI ID

18319

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Laikind PK, Seegmiller JE, Gruber HE: Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity. Anal Biochem. 1986 Jul;156(1):81-90. doi: 10.1016/0003-2697(86)90158-2. [PubMed:3740420 ]
Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
Kmoch S, Hartmannova H, Stiburkova B, Krijt J, Zikanova M, Sebesta I: Human adenylosuccinate lyase (ADSL), cloning and characterization of full-length cDNA and its isoform, gene structure and molecular basis for ADSL deficiency in six patients. Hum Mol Genet. 2000 Jun 12;9(10):1501-13. doi: 10.1093/hmg/9.10.1501. [PubMed:10888601 ]
Race V, Marie S, Vincent MF, Van den Berghe G: Clinical, biochemical and molecular genetic correlations in adenylosuccinate lyase deficiency. Hum Mol Genet. 2000 Sep 1;9(14):2159-65. doi: 10.1093/hmg/9.14.2159. [PubMed:10958654 ]
Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3. doi: 10.1081/NCN-200027494. [PubMed:15571235 ]
Zikanova M, Krijt J, Hartmannova H, Kmoch S: Preparation of 5-amino-4-imidazole-N-succinocarboxamide ribotide, 5-amino-4-imidazole-N-succinocarboxamide riboside and succinyladenosine, compounds usable in diagnosis and research of adenylosuccinate lyase deficiency. J Inherit Metab Dis. 2005;28(4):493-9. doi: 10.1007/s10545-005-0493-z. [PubMed:15902552 ]
Keller KE, Tan IS, Lee YS: SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. Science. 2012 Nov 23;338(6110):1069-72. doi: 10.1126/science.1224409. Epub 2012 Oct 18. [PubMed:23086999 ]

Showing metabocard for SAICAR (MMDBc0029510)

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