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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-04-12 20:43:31 UTC
Update Date2020-02-26 21:26:12 UTC
HMDB IDHMDB0006032
Secondary Accession Numbers
  • HMDB06032
Metabolite Identification
Common NameImidazoleacetic acid ribotide
DescriptionImidazoleacetic 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
Data?1582752372
Synonyms
ValueSource
1-(5-Phosphoribosyl)imidazole-4-acetateChEBI
1-(5-Phosphoribosyl)imidazole-4-acetic acidGenerator
Imidazoleacetate ribotideGenerator
1-(5-Phosphoribosyl)imidazol-4-ylacetic acidHMDB
1-(5-Phosphoribosyl)imidazol-4-ylacetateHMDB
1-(5-O-Phosphono-b-D-ribofuranosyl)-1H-imidazole-4-acetic acidHMDB
1-(5-O-Phosphono-beta-delta-ribofuranosyl)-1H-imidazole-4-acetic acidHMDB
1-b-D-Ribofuranosyl-imidazole-4-acetic acid 5'-(dihydrogen phosphate)HMDB
1-b-D-Ribofuranosyl-imidazole-4-acetic acid 5'-phosphateHMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid 5'-(dihydrogen phosphate)HMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acid 5'-phosphateHMDB
1-Ribosylimidazole-4-acetic acid 5'-phosphateHMDB
Imidazole-4-acetic acid ribotideHMDB
[1-(5-Phosphoribofuranosyl)imidazol-4-yl]acetic acidHMDB
[1-(5-Phosphoribosyl)imidazol-4-yl]acetic acidHMDB
[1-(5-Phosphoribosyl)imidazol-4-yl]acetateGenerator
IAA-RPMeSH
Imidazoleacetic acid ribotideMeSH
Chemical FormulaC10H15N2O9P
Average Molecular Weight338.2079
Monoisotopic Molecular Weight338.0515166
IUPAC Name2-{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 Number2888-19-9
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 KeyRDQUQBHPMYFYMX-XIWVQZPPSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Imidazole ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Imidazolyl carboxylic acid derivative
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.74 g/LALOGPS
logP-1.7ALOGPS
logP-3.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)5.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area171.57 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity67.42 m³·mol⁻¹ChemAxon
Polarizability28.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9622000000-07b4b17f1a1ad8050f8bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00lr-3913320000-d825e0822aeba9470cc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0adi-0916000000-8ac088c646a69f3ebb61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1900000000-c1259bc5491344653f92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-6900000000-88cf23a9404395cb56dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-6719000000-a878fa2d4fa77733382eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-c2e99300d58257e2d11aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c1a945dcf895b2caca65Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023810
KNApSAcK IDNot Available
Chemspider ID13148709
KEGG Compound IDC04437
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16019958
PDB IDNot Available
ChEBI ID16805
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceMatulic-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
  1. 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 ]