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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 20:52:31 UTC

Update Date

2021-09-14 15:47:19 UTC

HMDB ID

HMDB0006273

Secondary Accession Numbers

HMDB06273

Metabolite Identification

Common Name

5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid

Description

5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid, also known as 1-(5'-phosphoribosyl)-4-carboxy-5-aminoimidazole or 1-(5-phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is a very strong basic compound (based on its pKa). 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid exists in all living species, ranging from bacteria to humans. Within humans, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid participates in a number of enzymatic reactions. In particular, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid can be converted into 5-aminoimidazole ribonucleotide; which is mediated by the enzyme multifunctional protein ADE2. In addition, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid and L-aspartic acid can be converted into SAICAR; which is mediated by the enzyme multifunctional protein ADE2. In humans, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is involved in the metabolic disorder called Lesch-Nyhan syndrome (LNS). Outside of the human body, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid has been detected, but not quantified in, several different foods, such as ohelo berries, Chinese mustards, peach (var.), jackfruits, and saskatoon berries. This could make 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid a potential biomarker for the consumption of these foods. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is an intermediate in purine metabolism. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase (EC: 4.1.1.21).

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303062019532D          

 22 23  0  0  0  0            999 V2000
10001.7525 9999.2289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.152210000.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.868710000.5597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1522 9999.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5881 9998.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.330910000.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7981 9998.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.615710000.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.900310000.5597    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.312410001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.181210000.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.486610001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.711410000.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.044010000.1558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2989 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.1239 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.378810000.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.770610000.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.438010000.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.183110001.3351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.358110001.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.103210000.5505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 21 22  1  0  0  0  0
 16  5  1  6  0  0  0
 14  6  1  1  0  0  0
 15  7  1  6  0  0  0
  1 18  1  0  0  0  0
 17 22  1  1  0  0  0
 19  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006273

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1

> <INCHI_KEY>
XFVULMDJZXYMSG-ZIYNGMLESA-N

> <FORMULA>
C9H14N3O9P

> <MOLECULAR_WEIGHT>
339.1959

> <EXACT_MASS>
339.046765573

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.489435960826928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-3.7317525536992675

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.25890510038018

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1825891616118538

> <JCHEM_PKA_STRONGEST_BASIC>
7.112770228283477

> <JCHEM_POLAR_SURFACE_AREA>
197.59

> <JCHEM_REFRACTIVITY>
67.3199

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/NC1=C(N=CN1%5BC@@H%5D1O%5BC@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:35})
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.7813    1.0469    1.2308 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.0490    0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -1.0176   -0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0241   -1.7546   -0.8225 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8524   -1.2054   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443   -0.0893    0.0686 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420    0.8049    0.4314 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9746    1.1767    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    0.1191    0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130    1.1645    0.1938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6271    1.5932    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945    0.6178   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987   -0.3254    0.4484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -1.1009    0.1042 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9817   -2.1739    1.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757   -0.0413    0.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247   -1.8013   -1.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    2.2226   -0.7266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0698    2.0666   -1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    3.5404   -0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543    1.9822   -0.5649 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2011    1.7064   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3915    3.1453   -0.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631   -1.2973    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8959   -2.3765   -0.6092 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0721   -0.5566    0.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    1.0469    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093    1.7509    1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -1.5775   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.4387   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533    0.1269   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7939   -2.6792    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0266    0.4556    0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    4.2443   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    3.9285   -0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8472   -2.4782   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 29  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 32  1  0  0  0  0
 16 33  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 20 34  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 35  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 36  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  N   UNK     0    8669.9388665.227   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8672.5518666.941   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8673.8888667.711   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.5518665.399   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.7648664.236   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8663.5518667.711   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8664.4238664.252   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8662.2168666.941   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0    8660.8818667.711   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0    8661.6508669.049   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8659.5388666.937   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8660.1088669.049   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8666.1288667.863   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8664.8828666.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3588665.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.8988665.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3748666.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.9728666.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8671.2188667.694   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8670.7428669.159   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8669.2028669.159   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8668.7268667.694   0.000  0.00  0.00           N+0
CONECT    1   18                                                            
CONECT    2    3    4   19                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   16                                                            
CONECT    6    8   14                                                       
CONECT    7   15                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   14   17                                                       
CONECT   14   15   13    6                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   13   22                                                  
CONECT   18   19   22    1                                                  
CONECT   19   18   20    2                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   18   21   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/NC1=C(N=CN1%5BC@@H%5D1O%5BC@H%5... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1       3.781   1.047   1.231  1.00  0.00           N  
HETATM    2  C   UNL     1       3.249   0.049   0.442  1.00  0.00           C  
HETATM    3  CA  UNL     1       3.933  -1.018  -0.126  1.00  0.00           C  
HETATM    4  N   UNL     1       3.024  -1.755  -0.823  1.00  0.00           N  
HETATM    5  C   UNL     1       1.852  -1.205  -0.711  1.00  0.00           C  
HETATM    6  N   UNL     1       1.944  -0.089   0.069  1.00  0.00           N  
HETATM    7  C   UNL     1       0.842   0.805   0.431  1.00  0.00           C  
HETATM    8  H   UNL     1       0.975   1.177   1.447  1.00  0.00           H  
HETATM    9  O   UNL     1      -0.423   0.119   0.308  1.00  0.00           O  
HETATM   10  C   UNL     1      -1.413   1.165   0.194  1.00  0.00           C  
HETATM   11  H   UNL     1      -1.627   1.593   1.173  1.00  0.00           H  
HETATM   12  C   UNL     1      -2.695   0.618  -0.439  1.00  0.00           C  
HETATM   13  O   UNL     1      -3.299  -0.325   0.448  1.00  0.00           O  
HETATM   14  P   UNL     1      -4.667  -1.101   0.104  1.00  0.00           P  
HETATM   15  O   UNL     1      -4.982  -2.174   1.262  1.00  0.00           O  
HETATM   16  O   UNL     1      -5.876  -0.041   0.012  1.00  0.00           O  
HETATM   17  O   UNL     1      -4.525  -1.801  -1.192  1.00  0.00           O  
HETATM   18  C   UNL     1      -0.765   2.223  -0.727  1.00  0.00           C  
HETATM   19  H   UNL     1      -1.070   2.067  -1.761  1.00  0.00           H  
HETATM   20  O   UNL     1      -1.113   3.540  -0.297  1.00  0.00           O  
HETATM   21  C   UNL     1       0.754   1.982  -0.565  1.00  0.00           C  
HETATM   22  H   UNL     1       1.201   1.706  -1.520  1.00  0.00           H  
HETATM   23  O   UNL     1       1.391   3.145  -0.033  1.00  0.00           O  
HETATM   24  C   UNL     1       5.363  -1.297   0.000  1.00  0.00           C  
HETATM   25  O   UNL     1       5.896  -2.377  -0.609  1.00  0.00           O  
HETATM   26  OXT UNL     1       6.072  -0.557   0.655  1.00  0.00           O  
HETATM   27  H   UNL     1       4.729   1.047   1.439  1.00  0.00           H  
HETATM   28  H   UNL     1       3.209   1.751   1.575  1.00  0.00           H  
HETATM   29  H   UNL     1       0.944  -1.577  -1.161  1.00  0.00           H  
HETATM   30  H   UNL     1      -3.387   1.439  -0.623  1.00  0.00           H  
HETATM   31  H   UNL     1      -2.453   0.127  -1.382  1.00  0.00           H  
HETATM   32  H   UNL     1      -5.794  -2.679   1.121  1.00  0.00           H  
HETATM   33  H   UNL     1      -6.027   0.456   0.828  1.00  0.00           H  
HETATM   34  H   UNL     1      -0.733   4.244  -0.840  1.00  0.00           H  
HETATM   35  H   UNL     1       1.313   3.929  -0.594  1.00  0.00           H  
HETATM   36  H   UNL     1       6.847  -2.478  -0.468  1.00  0.00           H  
CONECT    1    2   27   28                                            
CONECT    2    1    3    3    6                                       
CONECT    3    2    2    4   24                                       
CONECT    4    3    5    5                                            
CONECT    5    4    4    6   29                                       
CONECT    6    5    2    7                                            
CONECT    7    6    8    9   21                                       
CONECT    8    7                                                      
CONECT    9    7   10                                                 
CONECT   10    9   11   12   18                                       
CONECT   11   10                                                      
CONECT   12   10   13   30   31                                       
CONECT   13   12   14                                                 
CONECT   14   13   15   16   17                                       
CONECT   14   17                                                      
CONECT   15   14   32                                                 
CONECT   16   14   33                                                 
CONECT   17   14   14                                                 
CONECT   18   10   19   20   21                                       
CONECT   19   18                                                      
CONECT   20   18   34                                                 
CONECT   21   18   22    7   23                                       
CONECT   22   21                                                      
CONECT   23   21   35                                                 
CONECT   24    3   25   26   26                                       
CONECT   25   24   36                                                 
CONECT   26   24   24                                                 
CONECT   27    1                                                      
CONECT   28    1                                                      
CONECT   29    5                                                      
CONECT   30   12                                                      
CONECT   31   12                                                      
CONECT   32   15                                                      
CONECT   33   16                                                      
CONECT   34   20                                                      
CONECT   35   23                                                      
CONECT   36   25                                                      
MASTER        0    0    0    0    0    0    0    0   36    0   36    0
END

https://cactus.nci.nih.gov/chemical/structure/NC1=C(N=CN1%5BC@@H%5D1O%5BC@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:35})
 36 37  0  0  0  0  0  0  0  0999 V2000
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    3.0241   -1.7546   -0.8225 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8524   -1.2054   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443   -0.0893    0.0686 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420    0.8049    0.4314 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9746    1.1767    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    0.1191    0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130    1.1645    0.1938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6271    1.5932    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945    0.6178   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987   -0.3254    0.4484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -1.1009    0.1042 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9817   -2.1739    1.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757   -0.0413    0.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247   -1.8013   -1.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    2.2226   -0.7266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0698    2.0666   -1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    3.5404   -0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543    1.9822   -0.5649 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2011    1.7064   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3915    3.1453   -0.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631   -1.2973    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8959   -2.3765   -0.6092 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0721   -0.5566    0.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9442   -1.5775   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.4387   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533    0.1269   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7939   -2.6792    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0266    0.4556    0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    4.2443   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8472   -2.4782   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
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 18 20  1  0  0  0  0
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 21 23  1  0  0  0  0
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(5'-Phosphoribosyl)-4-carboxy-5-aminoimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-carboxyimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylate	ChEBI
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylate	ChEBI
5'-Phosphoribosyl-4-carboxy-5-aminoimidazole	ChEBI
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylate	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylic acid	Generator
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid	Generator
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylic acid	Generator
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid	Generator
4-Carboxy-5-aminoimidazole ribonucleotide	HMDB
5'Phosphoribosyl-4-carboxy-5-aminoimidazole	HMDB
5-Amino-4-carboxyimidazole ribonucleotide	HMDB
5-Amino-4-imidazolecarboxylic acid ribonucleotide	HMDB
5-Aminoimidazole carboxilic acid ribonucleotice	HMDB
5-Aminoimidazole-4-carboxilic acid ribonucleotide	HMDB
Carboxyaminoimidazole ribonucleotide	HMDB
Carboxy-air	HMDB
AICOR	HMDB
Carboxyaminoimidazole ribotide	MeSH
CAIR	MeSH
5-Amino-1-(5-O-phosphonopentofuranosyl)-1H-imidazole-4-carboxylic acid	MeSH
1-(5’-Phosphoribosyl)-4-carboxy-5-aminoimidazole	HMDB
1-(5’-Phosphoribosyl)-5-amino-4-carboxyimidazole	HMDB
1-(5’-Phosphoribosyl)-5-amino-4-imidazolecarboxylate	HMDB
5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid	HMDB
5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid	HMDB
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate	HMDB
5-Aminoimidazole 4-carboxylic acid ribonucleotide	HMDB
5-Aminoimidazolecarboxylic acid ribonucleotide	HMDB
5’-Phosphoribosyl-4-carboxy-5-aminoimidazole	HMDB
5’-Phosphoribosyl-5-amino-4-imidazolecarboxylate	HMDB

Chemical Formula

C₉H₁₄N₃O₉P

Average Molecular Weight

339.1959

Monoisotopic Molecular Weight

339.046765573

IUPAC Name

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid

Traditional Name

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid

CAS Registry Number

6001-14-5

SMILES

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

InChI Identifier

InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1

InChI Key

XFVULMDJZXYMSG-ZIYNGMLESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Imidazole ribonucleoside
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Imidazole-4-carbonyl group
Alkyl phosphate
Phosphoric acid ester
Aminoimidazole
Organic phosphoric acid derivative
N-substituted imidazole
Azole
Vinylogous amide
Tetrahydrofuran
Imidazole
Heteroaromatic compound
1,2-diol
Secondary alcohol
Amino acid
Amino acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazole (CHEBI:28413 )
aminoimidazole (CHEBI:28413 )
imidazole-4-carboxylic acid (CHEBI:28413 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.81 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	7.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	197.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.32 m³·mol⁻¹	ChemAxon
Polarizability	28.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9613000000-2a087bcb710ee7b50b52	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00lu-2923230000-25e41df497cf1b5c9281	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9802000000-be91bc4ad090c354ffde	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0914000000-87d6bac417ced888900f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-1900000000-e298883e772e11c253f0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-8900000000-82583bffa17f1262d918	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-8928000000-d296c2812c7b06149794	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9400000000-76793052d8d2699d70dd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a8b367167e97f6df3690	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0539000000-deee029059e464053ab9	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-c7cafadad92d61fbb8a1	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01u0-7900000000-97962f3ed9f96ac07b6a	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3009000000-ff79299d0fd8156f9b05	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a211e114c93b066eaf36	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-bfdd206a6413421623ed	2021-09-08	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023871

KNApSAcK ID

Not Available

Chemspider ID

144983

KEGG Compound ID

C04751

BioCyc ID

PHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE

BiGG ID

44477

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

165388

PDB ID

C2R

ChEBI ID

28413

Food Biomarker Ontology

Not Available

VMH ID

5AIZC

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Multifunctional protein ADE2

General function:: Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:: Not Available
Gene Name:: PAICS
Uniprot ID:: P22234
Molecular weight:: 47078.82

Reactions

Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid + L-Aspartic acid → ADP + Phosphate + SAICAR	details
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid → 5-Aminoimidazole ribonucleotide + CO(2)	details
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid → 5-Aminoimidazole ribonucleotide + Carbon dioxide	details
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid + L-Aspartic acid → ADP + Phosphate + SAICAR	details

Showing metabocard for 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid (HMDB0006273)

MOL for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

3D MOL for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

3D SDF for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

3D-SDF for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

PDB for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

3D PDB for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

SMILES for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

INCHI for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

Structure for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

3D Structure for HMDB0006273 (5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid)

GC-MS

LC-MS/MS

Enzymes

Reactions