MiMeDB: Showing metabocard for 5'-Phosphoribosyl-N-formylglycineamide (MMDBc0029613)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:34:35 UTC

Update Date

2022-08-31 13:59:44 UTC

Metabolite ID

MMDBc0029613

Metabolite Identification

Common Name

5'-Phosphoribosyl-N-formylglycineamide

Description

5'-Phosphoribosyl-N-formylglycineamide (also known as FGAR or N-Formyl-GAR) is a substrate for Phosphoribosylformylglycinamidine synthase. It is involved in aminoimidazole ribonucleotide biosynthesis and plays a vital role in purine metabolism as well as the conversion of glutamine to glutamate. 5'-Phosphoribosyl-N-formylglycineamide is described as a glycinamide ribonucleotide having a phosphate group at the 5-position and a formyl group on the glycine nitrogen.

Structure

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

HMDB0001308
     RDKit          3D
5'-Phosphoribosyl-N-formylglycinamide
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.9051    2.2268    1.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7095    2.5532    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977    1.5266    0.8699 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.1387    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -0.7346    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.9936    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5607   -0.3385    0.8132 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -1.2483    0.7777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1585   -1.1457   -0.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -1.1876   -0.2688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3209   -0.6698   -1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325    0.6554   -1.7315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9446    1.1822   -3.0332 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0069    2.1323   -2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7347   -0.0630   -3.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9394    1.9874   -4.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814   -0.3333    0.9769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9206   -0.4349    1.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930   -1.0210    1.8121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1435   -2.2491    2.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    3.5705    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    1.8794    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151   -0.0855    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673    0.0667    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    0.6491    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476   -2.2727    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699   -2.1940   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.2922   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3941   -0.7318   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205    0.0285   -3.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159    2.9449   -3.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.7132    0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6086   -0.8176    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -0.4730    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.9685    1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 10 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  8  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  1
 10 27  1  1
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  6
 18 33  1  0
 19 34  1  1
 20 35  1  0
M  END


  Mrv1652304082023362D          

 20 20  0  0  0  0            999 V2000
 9999.311810000.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.597210000.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.882610000.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7787 9998.7115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.079110000.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5699 9998.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.792510000.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.507810000.5633    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.095510001.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.221210000.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.920210001.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.692010000.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.024610000.1600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.2795 9999.3754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1045 9999.3754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.359410000.1600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5972 9999.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.738710000.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.453310000.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.168110000.1510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13  1  1  6  0  0  0
 14  4  1  1  0  0  0
 16  5  1  6  0  0  0
 15  6  1  1  0  0  0
  2  3  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
  3 20  1  0  0  0  0
  2 17  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029613

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1

> <INCHI_KEY>
VDXLUNDMVKSKHO-XVFCMESISA-N

> <FORMULA>
C8H15N2O9P

> <MOLECULAR_WEIGHT>
314.1865

> <EXACT_MASS>
314.0515166

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.651467502321367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.28

> <JCHEM_LOGP>
-3.867787448666667

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.251389402211153

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2263355568590275

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5302762200112934

> <JCHEM_POLAR_SURFACE_AREA>
174.64999999999998

> <JCHEM_REFRACTIVITY>
60.248099999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001308
     RDKit          3D
5'-Phosphoribosyl-N-formylglycinamide
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.9051    2.2268    1.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7095    2.5532    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977    1.5266    0.8699 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.1387    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -0.7346    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.9936    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5607   -0.3385    0.8132 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -1.2483    0.7777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1585   -1.1457   -0.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -1.1876   -0.2688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3209   -0.6698   -1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325    0.6554   -1.7315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9446    1.1822   -3.0332 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0069    2.1323   -2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7347   -0.0630   -3.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9394    1.9874   -4.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814   -0.3333    0.9769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9206   -0.4349    1.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930   -1.0210    1.8121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1435   -2.2491    2.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    3.5705    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    1.8794    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151   -0.0855    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673    0.0667    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    0.6491    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476   -2.2727    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699   -2.1940   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.2922   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3941   -0.7318   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205    0.0285   -3.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159    2.9449   -3.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.7132    0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6086   -0.8176    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -0.4730    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.9685    1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 10 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  8  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  1
 10 27  1  1
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  6
 18 33  1  0
 19 34  1  1
 20 35  1  0
M  END

HEADER    PROTEIN                                 08-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-APR-20         0                                  
HETATM    1  N   UNK     0    8665.3828667.718   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8664.0488666.949   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.7148667.718   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8666.2548664.261   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8670.5488667.718   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8669.5978664.246   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8671.8798666.949   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0    8673.2158667.718   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0    8672.4458669.050   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8674.5468666.949   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8673.9848669.050   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8667.9588667.871   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8666.7138666.965   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.1888665.501   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.7288665.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.2048666.965   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8664.0488665.408   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8658.7128666.949   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8660.0468667.718   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8661.3808666.949   0.000  0.00  0.00           N+0
CONECT    1    2   13                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2   20                                                       
CONECT    4   14                                                            
CONECT    5    7   16                                                       
CONECT    6   15                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16                                                       
CONECT   13   14   12    1                                                  
CONECT   14   13   15    4                                                  
CONECT   15   14   16    6                                                  
CONECT   16   15   12    5                                                  
CONECT   17    2                                                            
CONECT   18   19                                                            
CONECT   19   18   20                                                       
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0001308
HETATM    1  O1  UNL     1       5.905   2.227   1.024  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.710   2.553   0.886  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.698   1.527   0.870  1.00  0.00           N  
HETATM    4  C2  UNL     1       4.064   0.139   1.013  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.893  -0.735   0.970  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.187  -1.994   1.096  1.00  0.00           O  
HETATM    7  N2  UNL     1       1.561  -0.338   0.813  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.435  -1.248   0.778  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.159  -1.146  -0.479  1.00  0.00           O  
HETATM   10  C5  UNL     1      -1.534  -1.188  -0.269  1.00  0.00           C  
HETATM   11  C6  UNL     1      -2.321  -0.670  -1.423  1.00  0.00           C  
HETATM   12  O4  UNL     1      -2.033   0.655  -1.732  1.00  0.00           O  
HETATM   13  P1  UNL     1      -2.945   1.182  -3.033  1.00  0.00           P  
HETATM   14  O5  UNL     1      -4.007   2.132  -2.502  1.00  0.00           O  
HETATM   15  O6  UNL     1      -3.735  -0.063  -3.834  1.00  0.00           O  
HETATM   16  O7  UNL     1      -1.939   1.987  -4.117  1.00  0.00           O  
HETATM   17  C7  UNL     1      -1.681  -0.333   0.977  1.00  0.00           C  
HETATM   18  O8  UNL     1      -2.921  -0.435   1.552  1.00  0.00           O  
HETATM   19  C8  UNL     1      -0.593  -1.021   1.812  1.00  0.00           C  
HETATM   20  O9  UNL     1      -1.143  -2.249   2.200  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.420   3.570   0.779  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.726   1.879   0.750  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.815  -0.086   0.221  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.567   0.067   2.017  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.271   0.649   0.709  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.848  -2.273   0.897  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.870  -2.194  -0.010  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.074  -1.292  -2.307  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.394  -0.732  -1.161  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.720   0.028  -3.830  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.916   2.945  -3.823  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.385   0.713   0.736  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.609  -0.818   0.978  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.318  -0.473   2.692  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.804  -2.968   1.640  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8   25
CONECT    8    9   19   26
CONECT    9   10
CONECT   10   11   17   27
CONECT   11   12   28   29
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   30
CONECT   16   31
CONECT   17   18   19   32
CONECT   18   33
CONECT   19   20   34
CONECT   20   35
END

HMDB0001308
     RDKit          3D
5'-Phosphoribosyl-N-formylglycinamide
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.9051    2.2268    1.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7095    2.5532    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977    1.5266    0.8699 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.1387    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -0.7346    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.9936    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5607   -0.3385    0.8132 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -1.2483    0.7777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1585   -1.1457   -0.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -1.1876   -0.2688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3209   -0.6698   -1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325    0.6554   -1.7315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9446    1.1822   -3.0332 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0069    2.1323   -2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7347   -0.0630   -3.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9394    1.9874   -4.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814   -0.3333    0.9769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9206   -0.4349    1.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930   -1.0210    1.8121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1435   -2.2491    2.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    3.5705    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    1.8794    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151   -0.0855    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673    0.0667    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    0.6491    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476   -2.2727    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699   -2.1940   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.2922   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3941   -0.7318   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205    0.0285   -3.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159    2.9449   -3.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.7132    0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6086   -0.8176    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -0.4730    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.9685    1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 10 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  8  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  1
 10 27  1  1
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  6
 18 33  1  0
 19 34  1  1
 20 35  1  0
M  END

Synonyms

Value	Source
N-Formyl-gar	Kegg
N-Formylglycinamide ribonucleotide	Kegg
N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide	Kegg
5'-p-Ribosyl-N-formylglycineamide	HMDB
5'-Phosphoribosyl-formylglycinamide	HMDB
5'-Phosphoribosyl-N-formylglycineamide	HMDB
5-Phosphoribosyl-N-formalglycineamide	HMDB
FGAR	HMDB
N(2)-Formyl-N(1)-(5-phospho-D-ribosyl)glycinamide	HMDB
Formylglycinamide ribonucleotide	HMDB
Formylglycineamideribotide	HMDB
Phosphoribosyl-N-formylglycineamide	HMDB
2-(Formylamino)-N-(5-O-phosphono-beta-D-ribofuranosyl)acetamide	HMDB
2-(Formylamino)-N-(5-O-phosphono-β-D-ribofuranosyl)acetamide	HMDB
5'-Phosphoribosyl-N-formylglycinamide	HMDB
5’-Phosphoribosyl-N-formylglycinamide	HMDB
Formylglycinamide ribotide	HMDB
Phosphoribosylformylglycinamide	HMDB
alpha-N-Formylglycinamide ribonucleotide	HMDB
α-N-Formylglycinamide ribonucleotide	HMDB

Molecular Formula

C₈H₁₅N₂O₉P

Average Mass

314.1865

Monoisotopic Mass

314.0515166

IUPAC Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O

InChI Identifier

InChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1

InChI Key

VDXLUNDMVKSKHO-XVFCMESISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinamide ribonucleotides. Glycinamide ribonucleotides are compounds in which the amide N atom of glycineamide is linked to the C-1 of a ribosyl (or deoxyribosyl) moiety. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Glycinamide ribonucleotides

Sub Class

Not Available

Direct Parent

Glycinamide ribonucleotides

Alternative Parents

Substituents

Glycinamide-ribonucleotide
Pentose phosphate
Pentose-5-phosphate
N-formyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-formyl-alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Monosaccharide phosphate
Pentose monosaccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Alkyl phosphate
Monosaccharide
Phosphoric acid ester
Tetrahydrofuran
Secondary carboxylic acid amide
1,2-diol
Carboxamide group
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-glycosyl compound (CHEBI:42411 )
ribose monophosphate (CHEBI:42411 )
amido monocarboxylic acid amide (CHEBI:42411 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.52 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.9	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	174.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.25 m³·mol⁻¹	ChemAxon
Polarizability	25.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9330000000-47bd3a51454a22349c16	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0089-5972200000-28cbe677e79c994d5692	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9121000000-70e7f7e392d67c9062d7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9110000000-24b14d3360fd37fa0b5a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-6c2f243f9e36f7267013	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01r6-8914000000-411b5cf47e3e7e5511fd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-fc9464d8ad7b3b1ac820	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ccc93e5e04249a7f1425	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0079000000-0c457b0a6a5c25c65962	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2920000000-569fd550eacc61a8bd6c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2900000000-32e3418d15835aba1b7b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-9036000000-b8480e9ce9f70df638e9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-14698f4417bb19153972	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-e93ac01407977ed80740	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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
MMDBp0191999	Trifunctional purine biosynthetic protein adenosine-3	Enzyme	P22102	Homo sapiens
MMDBp0192473	Phosphoribosylformylglycinamidine synthase	Enzyme	O15067	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001270	10-Formyltetrahydrofolic acid	5'-Phosphoribosyl-N-formylglycineamide	phosphoribosylglycinamide formyltransferase, phosphoribosylglycinamide synthetase, phosphoribosylaminoimidazole synthetase	VMH; KEGG	12450384 2183217 9328467 9473452
MMDBr0006939	10-Formyltetrahydrofolic acid	5'-Phosphoribosyl-N-formylglycineamide	Not Available	VMH	30371894
MMDBr0007063	Formic acid	5'-Phosphoribosyl-N-formylglycineamide	Not Available	VMH	30371894
MMDBr0007946	5'-Phosphoribosyl-N-formylglycineamide	Phosphoribosylformylglycineamidine	Not Available	VMH	30371894

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	182	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	Firmicutes	381	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	Actinobacteria	127	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	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	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	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001308

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE

BiGG ID

43690

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

130805

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 5'-Phosphoribosyl-N-formylglycineamide (MMDBc0029613)

MOL for #<Metabolite:0x00007fece85fd4a8>

3D MOL for #<Metabolite:0x00007fece85fd4a8>

3D SDF for #<Metabolite:0x00007fece85fd4a8>

3D-SDF for #<Metabolite:0x00007fece85fd4a8>

PDB for #<Metabolite:0x00007fece85fd4a8>

3D PDB for #<Metabolite:0x00007fece85fd4a8>

SMILES for #<Metabolite:0x00007fece85fd4a8>

INCHI for #<Metabolite:0x00007fece85fd4a8>

Structure for #<Metabolite:0x00007fece85fd4a8>

3D Structure for #<Metabolite:0x00007fece85fd4a8>