MiMeDB: Showing metabocard for N5-Carboxyaminoimidazole ribonucleotide (MMDBc0029616)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:34:41 UTC

Update Date

2022-08-31 13:59:47 UTC

Metabolite ID

MMDBc0029616

Metabolite Identification

Common Name

N5-Carboxyaminoimidazole ribonucleotide

Description

N5-carboxyaminoimidazole ribonucleotide is a member of the chemical class known as 1-Phosphoribosyl-imidazoles. These are organic compounds containing the imidazole ring linked to a ribose phosphate through a 1-2 bond. The carbamic acid, N5-carboxyaminoimidazole ribonucleotide (N5-CAIR) is an intermediate in purine biosynthesis in E. coli. (PMID 7918411 ) Formation of 4-carboxy-5-aminoimidazole ribonucleotide (CAIR) in the purine pathway in most prokaryotes requires ATP, HCO3-, aminoimidazole ribonucleotide (AIR), and the gene products PurK and PurE. PurK catalyzes the conversion of AIR to N5-carboxyaminoimidazole ribonucleotide (N5-CAIR) in a reaction that requires both ATP and HCO3-. PurE catalyzes the unusual rearrangement of N5-CAIR to CAIR.

Structure

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

HMDB0012268
     RDKit          3D
N5-Carboxyaminoimidazole ribonucleotide
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.8579    1.0946   -0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863    1.6030    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3465    2.7171    1.0096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    1.0619    0.3421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718   -0.0781   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.8495   -1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -1.8233   -1.7222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9574   -1.6930   -1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0295   -0.6309   -0.3463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135   -0.1474    0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0841    0.7053   -0.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.0873   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069    0.8755   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    0.1190   -0.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    0.8613    0.1071 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.8519    1.1589    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307   -0.1902   -0.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931    2.3232   -0.7120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -1.2548    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675   -1.4258    0.9434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -1.2637    1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6665   -2.5082    0.9407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7300    3.5630    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    1.5266    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303   -0.7205   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -2.3545   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528    0.3900    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    0.0035   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    1.8668   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    1.0203    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342   -0.2648   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413    2.8999   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -2.0432   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676   -2.3327    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022   -1.0716    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -3.2249    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  5  1  0
 21 10  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv0541 02241203542D          

 22 23  0  0  0  0            999 V2000
   15.0263   -9.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4795  -11.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0263  -11.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3045  -11.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2417  -10.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7895  -12.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5742  -12.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5742  -11.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8439   -9.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5107  -10.4864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6286   -9.5220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2417  -10.8989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5346  -13.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2417  -12.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6724  -10.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2308   -9.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2421  -11.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2421  -13.3360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4171  -12.5110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0670  -12.5110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7895  -11.1291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2421  -12.5110    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1  5  2  0  0  0  0
  2  4  1  0  0  0  0
  2 20  1  0  0  0  0
  3 12  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4 21  1  0  0  0  0
  5 12  1  0  0  0  0
  5 11  1  0  0  0  0
  6 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8 21  1  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  2  0  0  0  0
 17 22  1  0  0  0  0
 18 22  1  0  0  0  0
 19 22  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029616

> <DATABASE_NAME>
MIME

> <SMILES>
OC1C(COP(O)(O)=O)OC(C1O)N1C=NC=C1NC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N3O9P/c13-6-4(2-20-22(17,18)19)21-8(7(6)14)12-3-10-1-5(12)11-9(15)16/h1,3-4,6-8,11,13-14H,2H2,(H,15,16)(H2,17,18,19)

> <INCHI_KEY>
JHLXDWGVSYMXPL-UHFFFAOYSA-N

> <FORMULA>
C9H14N3O9P

> <MOLECULAR_WEIGHT>
339.1959

> <EXACT_MASS>
339.046765573

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
28.38011029681859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.13

> <JCHEM_LOGP>
-3.4212731610733864

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.2551828758389445

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1822089997363596

> <JCHEM_PKA_STRONGEST_BASIC>
5.825351746342738

> <JCHEM_POLAR_SURFACE_AREA>
183.6

> <JCHEM_REFRACTIVITY>
67.4528

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-ylcarbamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012268
     RDKit          3D
N5-Carboxyaminoimidazole ribonucleotide
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.8579    1.0946   -0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863    1.6030    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3465    2.7171    1.0096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    1.0619    0.3421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718   -0.0781   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.8495   -1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -1.8233   -1.7222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9574   -1.6930   -1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0295   -0.6309   -0.3463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135   -0.1474    0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0841    0.7053   -0.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.0873   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069    0.8755   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    0.1190   -0.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    0.8613    0.1071 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.8519    1.1589    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307   -0.1902   -0.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931    2.3232   -0.7120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -1.2548    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675   -1.4258    0.9434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -1.2637    1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6665   -2.5082    0.9407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7300    3.5630    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    1.5266    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303   -0.7205   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -2.3545   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528    0.3900    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    0.0035   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    1.8668   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    1.0203    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342   -0.2648   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413    2.8999   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -2.0432   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676   -2.3327    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022   -1.0716    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -3.2249    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  5  1  0
 21 10  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      28.049 -18.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.428 -22.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.049 -20.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.968 -22.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.585 -18.805   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.874 -23.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.339 -22.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.339 -21.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.975 -18.250   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      28.953 -19.575   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      25.440 -17.774   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      26.585 -20.345   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      23.398 -24.731   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      26.585 -23.695   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      23.655 -19.757   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      22.831 -17.220   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.119 -21.814   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      19.119 -24.894   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      17.579 -23.354   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      20.658 -23.354   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      23.874 -20.774   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      19.119 -23.354   0.000  0.00  0.00           P+0
CONECT    1   10    5                                                       
CONECT    2    4   20                                                       
CONECT    3   12   10                                                       
CONECT    4    2    6   21                                                  
CONECT    5    1   12   11                                                  
CONECT    6    4   13    7                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7   21   12                                                  
CONECT    9   11   15   16                                                  
CONECT   10    1    3                                                       
CONECT   11    5    9                                                       
CONECT   12    3    5    8                                                  
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17   22                                                            
CONECT   18   22                                                            
CONECT   19   22                                                            
CONECT   20    2   22                                                       
CONECT   21    4    8                                                       
CONECT   22   17   18   19   20                                             
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0012268
HETATM    1  O1  UNL     1      -5.858   1.095  -0.462  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.986   1.603   0.273  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.347   2.717   1.010  1.00  0.00           O  
HETATM    4  N1  UNL     1      -3.699   1.062   0.342  1.00  0.00           N  
HETATM    5  C2  UNL     1      -3.272  -0.078  -0.390  1.00  0.00           C  
HETATM    6  C3  UNL     1      -3.990  -0.850  -1.274  1.00  0.00           C  
HETATM    7  N2  UNL     1      -3.164  -1.823  -1.722  1.00  0.00           N  
HETATM    8  C4  UNL     1      -1.957  -1.693  -1.155  1.00  0.00           C  
HETATM    9  N3  UNL     1      -2.030  -0.631  -0.346  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.913  -0.147   0.465  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.084   0.705  -0.222  1.00  0.00           O  
HETATM   12  C6  UNL     1       1.089   0.087  -0.508  1.00  0.00           C  
HETATM   13  C7  UNL     1       2.307   0.875  -0.010  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.421   0.119  -0.376  1.00  0.00           O  
HETATM   15  P1  UNL     1       4.860   0.861   0.107  1.00  0.00           P  
HETATM   16  O5  UNL     1       4.852   1.159   1.600  1.00  0.00           O  
HETATM   17  O6  UNL     1       6.131  -0.190  -0.284  1.00  0.00           O  
HETATM   18  O7  UNL     1       5.093   2.323  -0.712  1.00  0.00           O  
HETATM   19  C8  UNL     1       1.141  -1.255   0.135  1.00  0.00           C  
HETATM   20  O8  UNL     1       2.267  -1.426   0.943  1.00  0.00           O  
HETATM   21  C9  UNL     1      -0.077  -1.264   1.022  1.00  0.00           C  
HETATM   22  O9  UNL     1      -0.667  -2.508   0.941  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.730   3.563   0.621  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.000   1.527   0.976  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.030  -0.721  -1.574  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.105  -2.354  -1.347  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.353   0.390   1.329  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.181   0.003  -1.630  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.315   1.867  -0.504  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.225   1.020   1.078  1.00  0.00           H  
HETATM   31  H9  UNL     1       6.134  -0.265  -1.272  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.641   2.900  -0.123  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.160  -2.043  -0.617  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.268  -2.333   1.298  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.202  -1.072   2.081  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.025  -3.225   0.665  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5   24
CONECT    5    6    6    9
CONECT    6    7   25
CONECT    7    8    8
CONECT    8    9   26
CONECT    9   10
CONECT   10   11   21   27
CONECT   11   12
CONECT   12   13   19   28
CONECT   13   14   29   30
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   31
CONECT   18   32
CONECT   19   20   21   33
CONECT   20   34
CONECT   21   22   35
CONECT   22   36
END

HMDB0012268
     RDKit          3D
N5-Carboxyaminoimidazole ribonucleotide
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.8579    1.0946   -0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863    1.6030    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3465    2.7171    1.0096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    1.0619    0.3421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718   -0.0781   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.8495   -1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -1.8233   -1.7222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9574   -1.6930   -1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0295   -0.6309   -0.3463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135   -0.1474    0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0841    0.7053   -0.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.0873   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069    0.8755   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    0.1190   -0.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    0.8613    0.1071 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.8519    1.1589    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307   -0.1902   -0.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931    2.3232   -0.7120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -1.2548    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675   -1.4258    0.9434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -1.2637    1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6665   -2.5082    0.9407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7300    3.5630    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    1.5266    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303   -0.7205   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -2.3545   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528    0.3900    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    0.0035   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    1.8668   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    1.0203    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342   -0.2648   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413    2.8999   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -2.0432   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676   -2.3327    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022   -1.0716    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -3.2249    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  5  1  0
 21 10  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

Synonyms

Not Available

Molecular Formula

C₉H₁₄N₃O₉P

Average Mass

339.1959

Monoisotopic Mass

339.046765573

IUPAC Name

(1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-5-yl)carbamic acid

Traditional Name

3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-ylcarbamic acid

CAS Registry Number

Not Available

SMILES

OC1C(COP(O)(O)=O)OC(C1O)N1C=NC=C1NC(O)=O

InChI Identifier

InChI=1S/C9H14N3O9P/c13-6-4(2-20-22(17,18)19)21-8(7(6)14)12-3-10-1-5(12)11-9(15)16/h1,3-4,6-8,11,13-14H,2H2,(H,15,16)(H2,17,18,19)

InChI Key

JHLXDWGVSYMXPL-UHFFFAOYSA-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
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Azole
Tetrahydrofuran
Imidazole
Heteroaromatic compound
1,2-diol
Secondary alcohol
Carbamic acid
Carbamic acid derivative
Carbonic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.61 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	5.83	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.45 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9612000000-5722225439944434ad4d	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00sm-2943230000-42a0f49332f8e2556acb	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	splash10-003s-7591000000-970c5624b39645aed12b	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9310000000-1441b2dce96bbc5db929	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9500000000-23b098a1732126b8098d	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00bl-7954000000-9e8d298dc1822d6c25fe	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-82766e450f45b224f699	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4f2eeb64dca4f0bece49	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-5009000000-3be6f9a582889568cde0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-529304ccd60c8b1224e3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-be9c5bbf9e6de7a0d5ba	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0459000000-29637aceea25bedae288	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9700000000-6d24c321dd69983d746f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9600000000-bcb1c202b2f95a2739c8	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
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

External Links

HMDB ID

HMDB0012268

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028906

KNApSAcK ID

Not Available

Chemspider ID

35032428

KEGG Compound ID

Not Available

BioCyc ID

CPD0-181

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25201011

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for N5-Carboxyaminoimidazole ribonucleotide (MMDBc0029616)

MOL for #<Metabolite:0x00005634bf015500>

3D MOL for #<Metabolite:0x00005634bf015500>

3D SDF for #<Metabolite:0x00005634bf015500>

3D-SDF for #<Metabolite:0x00005634bf015500>

PDB for #<Metabolite:0x00005634bf015500>

3D PDB for #<Metabolite:0x00005634bf015500>

SMILES for #<Metabolite:0x00005634bf015500>

INCHI for #<Metabolite:0x00005634bf015500>

Structure for #<Metabolite:0x00005634bf015500>

3D Structure for #<Metabolite:0x00005634bf015500>