MiMeDB: Showing metabocard for 5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide (MMDBc0055549)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:58:39 UTC

Update Date

2022-08-12 20:09:24 UTC

Metabolite ID

MMDBc0055549

Metabolite Identification

Common Name

5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

Description

phosphoribulosylformimino-AICAR-P 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. phosphoribulosylformimino-AICAR-P is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on phosphoribulosylformimino-AICAR-P.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221582D          

 43 44  0  0  1  0            999 V2000
   -3.4598    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    6.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4965    5.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    2.5320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8569    6.0975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3569    3.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    2.9445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4089    6.7106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1626    6.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5284    3.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032    4.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764    5.5545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3131    2.7845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1743    2.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888    3.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9090    4.4595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6895    5.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    3.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2374    7.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8771    6.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9154    2.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415    3.3570    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.4145    3.6590    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2395    2.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6707    8.2722    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.5184    8.0897    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.8532    7.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125    2.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    6.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2694    5.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    2.9445    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858    7.6048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    3.3570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613    6.8677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    2.1195    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0501    7.2297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8545    5.9257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8629    4.7576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  1  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  1  1  4  0  0  0
 17  4  2  0  0  0  0
 18  4  1  0  0  0  0
 18 14  1  0  0  0  0
 19  5  2  0  0  0  0
 19  9  1  0  0  0  0
 20  5  1  0  0  0  0
 20 14  1  0  0  0  0
 15 20  1  1  0  0  0
 21  6  2  0  0  0  0
  7 22  1  6  0  0  0
 10 23  1  1  0  0  0
 11 24  1  6  0  0  0
 12 25  1  6  0  0  0
 26 13  2  0  0  0  0
 33  2  1  0  0  0  0
 34  3  1  0  0  0  0
 35  8  1  0  0  0  0
 35 15  1  0  0  0  0
 36 27  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  2  0  0  0  0
 36 33  1  0  0  0  0
 37 30  1  0  0  0  0
 37 31  1  0  0  0  0
 37 32  2  0  0  0  0
 37 34  1  0  0  0  0
  7 38  1  6  0  0  0
  8 39  1  6  0  0  0
 10 40  1  1  0  0  0
 11 41  1  1  0  0  0
 12 42  1  1  0  0  0
 15 43  1  6  0  0  0
M  CHG  4  27  -1  28  -1  30  -1  31  -1
M  END


  Mrv1652306172221582D          

 43 44  0  0  1  0            999 V2000
   -3.4598    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    6.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4965    5.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    2.5320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8569    6.0975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3569    3.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    2.9445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4089    6.7106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1626    6.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5284    3.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032    4.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764    5.5545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3131    2.7845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1743    2.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888    3.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9090    4.4595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6895    5.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    3.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2374    7.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8771    6.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9154    2.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415    3.3570    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.4145    3.6590    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2395    2.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6707    8.2722    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.5184    8.0897    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.8532    7.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125    2.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    6.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2694    5.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    2.9445    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858    7.6048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    3.3570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613    6.8677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    2.1195    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0501    7.2297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8545    5.9257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8629    4.7576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  1  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  1  1  4  0  0  0
 17  4  2  0  0  0  0
 18  4  1  0  0  0  0
 18 14  1  0  0  0  0
 19  5  2  0  0  0  0
 19  9  1  0  0  0  0
 20  5  1  0  0  0  0
 20 14  1  0  0  0  0
 15 20  1  1  0  0  0
 21  6  2  0  0  0  0
  7 22  1  6  0  0  0
 10 23  1  1  0  0  0
 11 24  1  6  0  0  0
 12 25  1  6  0  0  0
 26 13  2  0  0  0  0
 33  2  1  0  0  0  0
 34  3  1  0  0  0  0
 35  8  1  0  0  0  0
 35 15  1  0  0  0  0
 36 27  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  2  0  0  0  0
 36 33  1  0  0  0  0
 37 30  1  0  0  0  0
 37 31  1  0  0  0  0
 37 32  2  0  0  0  0
 37 34  1  0  0  0  0
  7 38  1  6  0  0  0
  8 39  1  6  0  0  0
 10 40  1  1  0  0  0
 11 41  1  1  0  0  0
 12 42  1  1  0  0  0
 15 43  1  6  0  0  0
M  CHG  4  27  -1  28  -1  30  -1  31  -1
M  END
> <DATABASE_ID>
MMDBc0055549

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)C(=O)CN=CNC1=C(N=CN1[C@]1([H])O[C@]([H])(COP([O-])([O-])=O)[C@@]([H])(O)[C@@]1([H])O)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/p-4/t7-,8-,10+,11-,12-,15-/m1/s1

> <INCHI_KEY>
BLKFNHOCHNCLII-GHVQHMAVSA-J

> <FORMULA>
C15H21N5O15P2

> <MOLECULAR_WEIGHT>
573.303

> <EXACT_MASS>
573.053133312

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.317334994548425

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-5-{[({4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}amino)methylidene]amino}-2,3-dihydroxy-4-oxopentyl phosphate

> <JCHEM_LOGP>
-7.470165351894253

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.6690040229735423

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0317387936112246

> <JCHEM_PKA_STRONGEST_BASIC>
4.752113609585811

> <JCHEM_POLAR_SURFACE_AREA>
337.35999999999996

> <JCHEM_REFRACTIVITY>
111.49209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-5-{[({5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}amino)methylidene]amino}-2,3-dihydroxy-4-oxopentyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -6.458   5.496   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.124   5.496   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.668  11.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.126   5.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.127   9.658   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.125   4.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.457   4.726   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.200  11.382   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -11.866   7.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.791   5.496   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.230  12.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.637  11.900   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.186   5.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.459   7.806   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.476  10.368   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0     -13.651   5.198   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -7.792   4.726   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -9.126   7.036   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0     -12.897   8.324   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0     -10.620   9.338   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -5.125   3.186   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.457   3.186   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.791   7.036   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.910  14.033   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -10.971  12.670   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0     -11.042   4.643   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.877   6.266   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0       0.774   6.830   0.000  0.00  0.00           O-1
HETATM   29  O   UNK     0       2.314   4.163   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -6.852  15.442   0.000  0.00  0.00           O-1
HETATM   31  O   UNK     0      -4.701  15.101   0.000  0.00  0.00           O-1
HETATM   32  O   UNK     0      -7.193  13.290   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.210   4.726   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.042  12.950   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -7.970  10.048   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0       1.544   5.496   0.000  0.00  0.00           P+0
HETATM   37  P   UNK     0      -5.947  14.196   0.000  0.00  0.00           P+0
HETATM   38  H   UNK     0      -2.457   6.266   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.648  12.820   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.791   3.956   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      -9.427  13.496   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0     -10.928  11.061   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -9.077   8.881   0.000  0.00  0.00           H+0
CONECT    1    6   17                                                       
CONECT    2    7   33                                                       
CONECT    3    8   34                                                       
CONECT    4   17   18                                                       
CONECT    5   19   20                                                       
CONECT    6    1   10   21                                                  
CONECT    7    2   10   22   38                                             
CONECT    8    3   11   35   39                                             
CONECT    9   13   14   19                                                  
CONECT   10    6    7   23   40                                             
CONECT   11    8   12   24   41                                             
CONECT   12   11   15   25   42                                             
CONECT   13    9   16   26                                                  
CONECT   14    9   18   20                                                  
CONECT   15   12   20   35   43                                             
CONECT   16   13                                                            
CONECT   17    1    4                                                       
CONECT   18    4   14                                                       
CONECT   19    5    9                                                       
CONECT   20    5   14   15                                                  
CONECT   21    6                                                            
CONECT   22    7                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   36                                                            
CONECT   28   36                                                            
CONECT   29   36                                                            
CONECT   30   37                                                            
CONECT   31   37                                                            
CONECT   32   37                                                            
CONECT   33    2   36                                                       
CONECT   34    3   37                                                       
CONECT   35    8   15                                                       
CONECT   36   27   28   29   33                                             
CONECT   37   30   31   32   34                                             
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   15                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

Synonyms

Value	Source
5-[(5-Phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide	ChEBI
5-[(5-Phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamide	Generator
5-[(5-Phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamide	Generator

Molecular Formula

C₁₅H₂₁N₅O₁₅P₂

Average Mass

573.303

Monoisotopic Mass

573.053133312

IUPAC Name

(2R,3R)-5-{[({4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}amino)methylidene]amino}-2,3-dihydroxy-4-oxopentyl phosphate

Traditional Name

(2R,3R)-5-{[({5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}amino)methylidene]amino}-2,3-dihydroxy-4-oxopentyl phosphate

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)C(=O)CN=CNC1=C(N=CN1[C@]1([H])O[C@]([H])(COP([O-])([O-])=O)[C@@]([H])(O)[C@@]1([H])O)C(N)=O

InChI Identifier

InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/p-4/t7-,8-,10+,11-,12-,15-/m1/s1

InChI Key

BLKFNHOCHNCLII-GHVQHMAVSA-J

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 phosphate
Pentose-5-phosphate
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
2-heteroaryl carboxamide
Imidazole-4-carbonyl group
N-substituted imidazole
Organic phosphoric acid derivative
Acyloin
Beta-hydroxy ketone
Phosphoric acid ester
Alkyl phosphate
Monosaccharide
Tetrahydrofuran
Alpha-hydroxy ketone
Imidazole
Vinylogous amide
Azole
Heteroaromatic compound
Primary carboxylic acid amide
Ketone
Carboxamide group
Secondary alcohol
Formamidine
Amidine
Carboxylic acid amidine
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:58525 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-7.5	ChemAxon
pKa (Strongest Acidic)	1.03	ChemAxon
pKa (Strongest Basic)	4.75	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	337.36 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	111.49 m³·mol⁻¹	ChemAxon
Polarizability	47.32 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

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013431	1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide	5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide	1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase	Isomerization	RHEA	34755880
MMDBr0017916	5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide	AICAR	Imidazole glycerol phosphate synthase subunit HisH	Synthesis	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Cyanobacteria	35	Human
Bacteria	Firmicutes	101	Human feces; Human ; Catfish ; Cattle
Bacteria	Proteobacteria	376	Human ; Human feces; Pig ; Cattle ; River trout ; Turkey ; Sheep ; Chicken ; Human subgingival plaque
Bacteria	Actinobacteria	59	Human ; Human feces; Cattle
Bacteria	Aquificae	4
Archaea/Archaea	Euryarchaeota	31
Eukaryota/Fungi	Ascomycota	10	Human feces; Human saliva; Human supragingival plaque
Bacteria/NULL	Proteobacteria	3	Human ; Human feces; Pig ; Cattle ; River trout ; Turkey ; Sheep ; Chicken ; Human subgingival plaque
Bacteria	Bacteroidetes	11	Human ; Human feces
Bacteria	Spirochaetes	8	Pig ; Human
Archaea/Archaea	Thaumarchaeota	2
Bacteria	Chloroflexi	10
Bacteria	Chlorobi	11
Bacteria	Deinococcus-thermus	4
Bacteria	Dictyoglomi	2
Bacteria	Elusimicrobia	2
Bacteria	Gemmatimonadetes	1
Archaea	Euryarchaeota	4
Archaea/Archaea	nah	1
Bacteria	Verrucomicrobia	2	Human ; Human feces
Archaea/Archaea	Crenarchaeota	5
Bacteria	Planctomycetes	1
Archaea	Crenarchaeota	1
Bacteria	nah	1
Bacteria	Thermotogae	5
Bacteria	Nitrospirae	1
Bacteria/NULL	Spirochaetes	1	Pig ; Human
Bacteria	Acidobacteria	3
Bacteria/NULL	Firmicutes	1	Human feces; Human ; Catfish ; Cattle

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26331218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45266672

PDB ID

Not Available

ChEBI ID

58525

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide (MMDBc0055549)

MOL for #<Metabolite:0x00007f5a88058270>

3D MOL for #<Metabolite:0x00007f5a88058270>

3D SDF for #<Metabolite:0x00007f5a88058270>

3D-SDF for #<Metabolite:0x00007f5a88058270>

PDB for #<Metabolite:0x00007f5a88058270>

3D PDB for #<Metabolite:0x00007f5a88058270>

SMILES for #<Metabolite:0x00007f5a88058270>

INCHI for #<Metabolite:0x00007f5a88058270>

Structure for #<Metabolite:0x00007f5a88058270>

3D Structure for #<Metabolite:0x00007f5a88058270>