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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 20:43:31 UTC

Update Date

2021-09-14 15:38:59 UTC

HMDB ID

HMDB0006032

Secondary Accession Numbers

HMDB06032

Metabolite Identification

Common Name

Imidazoleacetic acid ribotide

Description

Imidazoleacetic acid ribotide (IAA-RP) is an endogenous ligand that stimulates imidazol(in)e receptors. Experimental data suggest that IAA-RP may participate in transsynaptic signaling in brain, because it exists in brainstem neurons, exhibits depolarization-induced Ca2+-dependent release from P2 synaptosomal elements, has relatively high affinity for membrane-bound I-R sites, and produces physiological effects on exogenous application. IAA-RP is rapidly metabolized by phosphatases and ecto-5'-nucleotidases. (PMID: 15365189 ).

Structure

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

HMDB0006032
     RDKit          3D
Imidazoleacetic acid ribotide
 37 38  0  0  0  0  0  0  0  0999 V2000
    6.7177    2.0384    1.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8083    1.5101    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1471    0.4734   -0.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    2.0521    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.9196    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654    1.0200   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -0.2158   -0.1553 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494   -0.5617   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    0.1688    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -0.5051   -0.4670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0929   -0.0877    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750    1.2666   -0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122    1.5451    0.5041 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8591    2.1069   -0.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216    2.5972    1.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5992    0.0692    1.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654   -1.9089    0.0679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2147   -2.8656   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -2.0062   -0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1548   -2.7690   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -1.0778    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -0.3822    0.5058 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.5182   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318    2.4370    1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    2.8624   -0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    1.9609   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -0.3487   -1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -0.5502   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.6189   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412   -0.3879    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7508    2.9846    1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7644    0.1095    2.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5481   -1.9030    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396   -3.6339   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -2.4348    0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941   -2.2282   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -2.1543    0.1849 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  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
  7 21  1  0
 21 22  2  0
 22  5  1  0
 19  8  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  1
 20 36  1  0
 21 37  1  0
M  END


  Mrv0541 02231220322D          

 22 23  0  0  1  0            999 V2000
   19.0493  -10.0977    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.5139   -8.0644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3944   -7.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9491   -9.5165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5644   -9.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7168   -9.6129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5343  -10.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3819  -10.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8933   -3.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5879   -3.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8465   -6.7545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4340   -5.4849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1790   -8.0644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4340   -8.8491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8465   -7.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2591   -8.8491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7439   -9.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5139   -6.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1790   -6.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2591   -5.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7439   -4.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4084   -4.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
 13  3  1  1  0  0  0
 14  4  1  1  0  0  0
  5 17  1  0  0  0  0
  9 22  1  0  0  0  0
 10 22  2  0  0  0  0
 11 15  1  0  0  0  0
 11 18  1  0  0  0  0
 11 19  1  0  0  0  0
 12 19  2  0  0  0  0
 12 20  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006032

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1O)N1C=NC(CC(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N2O9P/c13-7(14)1-5-2-12(4-11-5)10-9(16)8(15)6(21-10)3-20-22(17,18)19/h2,4,6,8-10,15-16H,1,3H2,(H,13,14)(H2,17,18,19)/t6-,8-,9-,10?/m1/s1

> <INCHI_KEY>
RDQUQBHPMYFYMX-XIWVQZPPSA-N

> <FORMULA>
C10H15N2O9P

> <MOLECULAR_WEIGHT>
338.2079

> <EXACT_MASS>
338.0515166

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
28.94000957343873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.74

> <JCHEM_LOGP>
-3.567933298842268

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.398128613729099

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2217870822945036

> <JCHEM_PKA_STRONGEST_BASIC>
5.904492152576091

> <JCHEM_POLAR_SURFACE_AREA>
171.57

> <JCHEM_REFRACTIVITY>
67.41760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006032
     RDKit          3D
Imidazoleacetic acid ribotide
 37 38  0  0  0  0  0  0  0  0999 V2000
    6.7177    2.0384    1.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8083    1.5101    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1471    0.4734   -0.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    2.0521    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.9196    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654    1.0200   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -0.2158   -0.1553 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494   -0.5617   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    0.1688    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -0.5051   -0.4670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0929   -0.0877    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750    1.2666   -0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122    1.5451    0.5041 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8591    2.1069   -0.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216    2.5972    1.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5992    0.0692    1.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654   -1.9089    0.0679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2147   -2.8656   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -2.0062   -0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1548   -2.7690   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -1.0778    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -0.3822    0.5058 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.5182   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318    2.4370    1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    2.8624   -0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    1.9609   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -0.3487   -1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -0.5502   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.6189   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412   -0.3879    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7508    2.9846    1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7644    0.1095    2.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5481   -1.9030    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396   -3.6339   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -2.4348    0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941   -2.2282   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -2.1543    0.1849 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  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
  7 21  1  0
 21 22  2  0
 22  5  1  0
 19  8  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  1
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      35.559 -18.849   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      32.693 -15.054   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      28.736 -14.578   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      29.772 -17.764   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      34.654 -17.603   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      36.805 -17.944   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      36.464 -20.095   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      34.313 -19.754   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      33.401  -6.340   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      30.964  -7.425   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      31.447 -12.608   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      30.677 -10.238   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      30.201 -15.054   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.677 -16.518   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.447 -14.149   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.217 -16.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.122 -17.764   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.693 -11.703   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.201 -11.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.217 -10.238   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.122  -8.993   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.496  -7.586   0.000  0.00  0.00           C+0
CONECT    1    5    6    7    8                                             
CONECT    2   15   16                                                       
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    1   17                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9   22                                                            
CONECT   10   22                                                            
CONECT   11   15   18   19                                                  
CONECT   12   19   20                                                       
CONECT   13    3   14   15                                                  
CONECT   14    4   13   16                                                  
CONECT   15    2   11   13                                                  
CONECT   16    2   14   17                                                  
CONECT   17    5   16                                                       
CONECT   18   11   20                                                       
CONECT   19   11   12                                                       
CONECT   20   12   18   21                                                  
CONECT   21   20   22                                                       
CONECT   22    9   10   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0006032
HETATM    1  O1  UNL     1       6.718   2.038   1.207  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.808   1.510   0.489  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.147   0.473  -0.349  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.423   2.052   0.608  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.493   0.920   0.399  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.165   1.020  -0.020  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.653  -0.216  -0.155  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.349  -0.562  -0.579  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.674   0.169   0.070  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.771  -0.505  -0.467  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.093  -0.088   0.057  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.375   1.267  -0.131  1.00  0.00           O  
HETATM   13  P1  UNL     1      -4.912   1.545   0.504  1.00  0.00           P  
HETATM   14  O5  UNL     1      -5.859   2.107  -0.524  1.00  0.00           O  
HETATM   15  O6  UNL     1      -4.822   2.597   1.839  1.00  0.00           O  
HETATM   16  O7  UNL     1      -5.599   0.069   1.038  1.00  0.00           O  
HETATM   17  C8  UNL     1      -1.465  -1.909   0.068  1.00  0.00           C  
HETATM   18  O8  UNL     1      -2.215  -2.866  -0.552  1.00  0.00           O  
HETATM   19  C9  UNL     1       0.021  -2.006  -0.282  1.00  0.00           C  
HETATM   20  O9  UNL     1       0.155  -2.769  -1.464  1.00  0.00           O  
HETATM   21  C10 UNL     1       2.645  -1.078   0.173  1.00  0.00           C  
HETATM   22  N2  UNL     1       3.741  -0.382   0.506  1.00  0.00           N  
HETATM   23  H1  UNL     1       6.674   0.518  -1.193  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.332   2.437   1.653  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.306   2.862  -0.136  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.621   1.961  -0.196  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.166  -0.349  -1.668  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.676  -0.550  -1.547  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.864  -0.619  -0.598  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.341  -0.388   1.088  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.751   2.985   1.898  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.764   0.109   2.006  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.548  -1.903   1.177  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.740  -3.634  -0.912  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.603  -2.435   0.542  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.194  -2.228  -2.225  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.641  -2.154   0.185  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5   24   25
CONECT    5    6    6   22
CONECT    6    7   26
CONECT    7    8   21
CONECT    8    9   19   27
CONECT    9   10
CONECT   10   11   17   28
CONECT   11   12   29   30
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   31
CONECT   16   32
CONECT   17   18   19   33
CONECT   18   34
CONECT   19   20   35
CONECT   20   36
CONECT   21   22   22   37
END

HMDB0006032
     RDKit          3D
Imidazoleacetic acid ribotide
 37 38  0  0  0  0  0  0  0  0999 V2000
    6.7177    2.0384    1.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8083    1.5101    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1471    0.4734   -0.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    2.0521    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.9196    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654    1.0200   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -0.2158   -0.1553 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494   -0.5617   -0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    0.1688    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -0.5051   -0.4670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0929   -0.0877    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750    1.2666   -0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122    1.5451    0.5041 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8591    2.1069   -0.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216    2.5972    1.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5992    0.0692    1.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654   -1.9089    0.0679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2147   -2.8656   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -2.0062   -0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1548   -2.7690   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -1.0778    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -0.3822    0.5058 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.5182   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318    2.4370    1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    2.8624   -0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    1.9609   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -0.3487   -1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -0.5502   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.6189   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412   -0.3879    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7508    2.9846    1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7644    0.1095    2.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5481   -1.9030    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396   -3.6339   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -2.4348    0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941   -2.2282   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -2.1543    0.1849 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  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
  7 21  1  0
 21 22  2  0
 22  5  1  0
 19  8  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  1
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(5-Phosphoribosyl)imidazole-4-acetate	ChEBI
1-(5-Phosphoribosyl)imidazole-4-acetic acid	Generator
Imidazoleacetate ribotide	Generator
IAA-RP	MeSH
1-(5-Phosphoribosyl)imidazol-4-ylacetic acid	ChEBI, HMDB
1-(5-Phosphoribosyl)imidazol-4-ylacetate	Generator, HMDB
1-(5-O-phosphono-b-D-Ribofuranosyl)-1H-imidazole-4-acetic acid	HMDB
1-(5-O-phosphono-beta-delta-Ribofuranosyl)-1H-imidazole-4-acetic acid	HMDB
1-b-D-Ribofuranosyl-imidazole-4-acetic acid 5'-(dihydrogen phosphate)	HMDB
1-b-D-Ribofuranosyl-imidazole-4-acetic acid 5'-phosphate	HMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid 5'-(dihydrogen phosphate)	HMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid 5'-phosphate	HMDB
1-Ribosylimidazole-4-acetic acid 5'-phosphate	HMDB
Imidazole-4-acetic acid ribotide	HMDB
[1-(5-Phosphoribofuranosyl)imidazol-4-yl]acetic acid	HMDB
[1-(5-Phosphoribosyl)imidazol-4-yl]acetic acid	HMDB
[1-(5-Phosphoribosyl)imidazol-4-yl]acetate	Generator, HMDB
Imidazoleacetic acid ribotide	MeSH

Chemical Formula

C₁₀H₁₅N₂O₉P

Average Molecular Weight

338.2079

Monoisotopic Molecular Weight

338.0515166

IUPAC Name

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

Traditional Name

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

CAS Registry Number

2888-19-9

SMILES

O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1O)N1C=NC(CC(O)=O)=C1

InChI Identifier

InChI=1S/C10H15N2O9P/c13-7(14)1-5-2-12(4-11-5)10-9(16)8(15)6(21-10)3-20-22(17,18)19/h2,4,6,8-10,15-16H,1,3H2,(H,13,14)(H2,17,18,19)/t6-,8-,9-,10?/m1/s1

InChI Key

RDQUQBHPMYFYMX-XIWVQZPPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Imidolactam
Pyrimidine
Monosaccharide
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organopnictogen compound
Primary amine
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0006032)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Guinea hen (FooDB: FOOD00373)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Elk (FooDB: FOOD00359)
Mule deer (FooDB: FOOD00348)

Lagomorph

Caprae

Domestic goat (FooDB: FOOD00529)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.74 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	5.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	171.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.42 m³·mol⁻¹	ChemAxon
Polarizability	28.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.145	31661259
DarkChem	[M-H]-	173.808	31661259
DeepCCS	[M+H]+	165.283	30932474
DeepCCS	[M-H]-	162.887	30932474
DeepCCS	[M-2H]-	196.033	30932474
DeepCCS	[M+Na]+	171.218	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imidazoleacetic acid ribotide	O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1O)N1C=NC(CC(O)=O)=C1	3819.9	Standard polar	33892256
Imidazoleacetic acid ribotide	O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1O)N1C=NC(CC(O)=O)=C1	2119.2	Standard non polar	33892256
Imidazoleacetic acid ribotide	O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1O)N1C=NC(CC(O)=O)=C1	2981.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Imidazoleacetic acid ribotide,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)OC(N2C=NC(CC(=O)O)=C2)[C@@H]1O	2780.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O)[C@H]1O	2826.1	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,1TMS,isomer #3	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=N1	2814.9	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,1TMS,isomer #4	C[Si](C)(C)OP(=O)(O)OC[C@H]1OC(N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O	2909.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2751.4	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #2	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O)[C@H]1O[Si](C)(C)C	2747.5	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)OC(N2C=NC(CC(=O)O)=C2)[C@@H]1O	2817.2	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #4	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2778.3	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #5	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@H]1O	2870.6	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #6	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=N1	2814.5	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TMS,isomer #7	C[Si](C)(C)OP(=O)(OC[C@H]1OC(N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	2877.0	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2720.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2770.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2794.9	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(N2C=NC(CC(=O)O)=C2)[C@@H]1O	2829.9	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #5	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2811.4	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #6	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1O	2871.6	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TMS,isomer #7	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=N1	2800.9	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2784.2	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2721.2	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	3539.9	Standard polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2788.8	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2737.1	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	3337.7	Standard polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #3	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2835.2	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #3	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2701.8	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #3	C[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3328.5	Standard polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #4	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2823.4	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #4	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2761.2	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TMS,isomer #4	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	3468.8	Standard polar	33892256
Imidazoleacetic acid ribotide,5TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2807.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,5TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2684.2	Standard non polar	33892256
Imidazoleacetic acid ribotide,5TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	3177.4	Standard polar	33892256
Imidazoleacetic acid ribotide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)OC(N2C=NC(CC(=O)O)=C2)[C@@H]1O	3041.4	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O)[C@H]1O	3078.6	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=N1	3080.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1OC(N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O	3150.3	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3218.3	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O)[C@H]1O[Si](C)(C)C(C)(C)C	3198.5	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(N2C=NC(CC(=O)O)=C2)[C@@H]1O	3283.3	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3234.5	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@H]1O	3317.6	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=N1	3289.1	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1OC(N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3333.8	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3408.8	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3453.2	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3466.0	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(N2C=NC(CC(=O)O)=C2)[C@@H]1O	3494.2	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3477.5	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1O	3524.4	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=N1	3491.2	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3649.7	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3409.8	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3728.9	Standard polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3648.5	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3390.7	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3594.2	Standard polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3679.9	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3318.8	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C(N2C=NC(CC(=O)O)=C2)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3599.8	Standard polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3661.4	Semi standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3420.8	Standard non polar	33892256
Imidazoleacetic acid ribotide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN(C2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3699.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazoleacetic acid ribotide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9622000000-07b4b17f1a1ad8050f8b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazoleacetic acid ribotide GC-MS (3 TMS) - 70eV, Positive	splash10-00lr-3913320000-d825e0822aeba9470cc8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazoleacetic acid ribotide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazoleacetic acid ribotide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 10V, Positive-QTOF	splash10-0adi-0916000000-8ac088c646a69f3ebb61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 20V, Positive-QTOF	splash10-0a6r-1900000000-c1259bc5491344653f92	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 40V, Positive-QTOF	splash10-004i-6900000000-88cf23a9404395cb56dc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 10V, Negative-QTOF	splash10-004r-6719000000-a878fa2d4fa77733382e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 20V, Negative-QTOF	splash10-004i-9300000000-c2e99300d58257e2d11a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 40V, Negative-QTOF	splash10-004i-9000000000-c1a945dcf895b2caca65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 10V, Negative-QTOF	splash10-00kr-2009000000-ef22e4150f9d194c213b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 20V, Negative-QTOF	splash10-004i-9100000000-705a000bdd895f74aaab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 40V, Negative-QTOF	splash10-004i-9000000000-0f29586b7272f8210253	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 10V, Positive-QTOF	splash10-0076-0595000000-5579b97c98df01da201c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 20V, Positive-QTOF	splash10-053r-5910000000-9164e0425ee1da339363	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazoleacetic acid ribotide 40V, Positive-QTOF	splash10-0560-7920000000-4d6cbc4f1980bf64bcaa	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB023810

KNApSAcK ID

Not Available

Chemspider ID

13148709

KEGG Compound ID

C04437

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16019958

PDB ID

Not Available

ChEBI ID

16805

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Matulic-Adamic, Jasenka; Watanabe, Kyoichi A. Nucleosides. 163. Synthesis of ribosides and ribotides of imidazole-4(5)-acetic acid and 1-methylimidazole-4(5)-acetic acid. Korean Journal of Medicinal Chemistry (1991), 1(1), 54-64.

Material Safety Data Sheet (MSDS)

Not Available

General References

Prell GD, Martinelli GP, Holstein GR, Matulic-Adamic J, Watanabe KA, Chan SL, Morgan NG, Haxhiu MA, Ernsberger P: Imidazoleacetic acid-ribotide: an endogenous ligand that stimulates imidazol(in)e receptors. Proc Natl Acad Sci U S A. 2004 Sep 14;101(37):13677-82. Epub 2004 Sep 13. [PubMed:15365189 ]

Showing metabocard for Imidazoleacetic acid ribotide (HMDB0006032)

MOL for HMDB0006032 (Imidazoleacetic acid ribotide)

3D MOL for HMDB0006032 (Imidazoleacetic acid ribotide)

3D SDF for HMDB0006032 (Imidazoleacetic acid ribotide)

3D-SDF for HMDB0006032 (Imidazoleacetic acid ribotide)

PDB for HMDB0006032 (Imidazoleacetic acid ribotide)

3D PDB for HMDB0006032 (Imidazoleacetic acid ribotide)

SMILES for HMDB0006032 (Imidazoleacetic acid ribotide)

INCHI for HMDB0006032 (Imidazoleacetic acid ribotide)

Structure for HMDB0006032 (Imidazoleacetic acid ribotide)

3D Structure for HMDB0006032 (Imidazoleacetic acid ribotide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra