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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2022-09-22 18:34:16 UTC
HMDB IDHMDB0002331
Secondary Accession Numbers
  • HMDB02331
Metabolite Identification
Common NameImidazoleacetic acid riboside
DescriptionImidazoleacetic acid riboside, also known as IAA-R or ribosylimidazole-4-acetic acid, belongs to the class of organic compounds known as imidazole ribonucleosides and ribonucleotides. These are organic compounds in which the C-1 of a ribosyl moiety is N-linked to an imidazole ring. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. This class does not contain benzimidazole nucleosides and nucleotides. Imidazoleacetic acid riboside has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make imidazoleacetic acid riboside a potential biomarker for the consumption of these foods. Imidazoleacetic acid riboside is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Imidazoleacetic acid riboside.
Structure
Data?1582752243
Synonyms
ValueSource
Imidazoleacetate ribosideGenerator
IAA-RMeSH
Ribosylimidazole-4-acetic acidMeSH
Ribosylimidazole acetic acidMeSH
1-b-D-Ribofuranosyl-imidazole-4-acetic acidHMDB
1-beta-delta-Ribofuranosyl-imidazole-4-acetic acidHMDB
1-Ribosylimidazole-4-acetic acidHMDB
RibosylimidazoleacetateHMDB
(1-Ribosylimidazole)-4-acetic acidGenerator, HMDB
Imidazoleacetic acid ribosideMeSH
Chemical FormulaC10H14N2O6
Average Molecular Weight258.228
Monoisotopic Molecular Weight258.08518619
IUPAC Name2-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}acetic acid
Traditional Nameribosylimidazole acetic acid
CAS Registry Number29605-99-0
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC(CC(O)=O)=C1
InChI Identifier
InChI=1S/C10H14N2O6/c13-3-6-8(16)9(17)10(18-6)12-2-5(11-4-12)1-7(14)15/h2,4,6,8-10,13,16-17H,1,3H2,(H,14,15)/t6-,8-,9-,10-/m1/s1
InChI KeyAHPWEWASPTZMEK-PEBGCTIMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazole ribonucleosides and ribonucleotides. These are organic compounds in which the C-1 of a ribosyl moiety is N-linked to an imidazole ring. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. This class does not contain benzimidazole nucleosides and nucleotides.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub ClassNot Available
Direct ParentImidazole ribonucleosides and ribonucleotides
Alternative Parents
Substituents
  • Imidazole ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazolyl carboxylic acid derivative
  • Monosaccharide
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility27 g/LALOGPS
logP-1.4ALOGPS
logP-3ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)6.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.04 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.54 m³·mol⁻¹ChemAxon
Polarizability24.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.76231661259
DarkChem[M-H]-156.40731661259
DeepCCS[M+H]+162.54830932474
DeepCCS[M-H]-160.15230932474
DeepCCS[M-2H]-193.60630932474
DeepCCS[M+Na]+168.69330932474
AllCCS[M+H]+158.332859911
AllCCS[M+H-H2O]+154.732859911
AllCCS[M+NH4]+161.532859911
AllCCS[M+Na]+162.532859911
AllCCS[M-H]-156.732859911
AllCCS[M+Na-2H]-156.632859911
AllCCS[M+HCOO]-156.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Imidazoleacetic acid ribosideOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC(CC(O)=O)=C13926.8Standard polar33892256
Imidazoleacetic acid ribosideOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC(CC(O)=O)=C12014.5Standard non polar33892256
Imidazoleacetic acid ribosideOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC(CC(O)=O)=C12409.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Imidazoleacetic acid riboside,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O2378.1Semi standard non polar33892256
Imidazoleacetic acid riboside,1TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(CC(=O)O)=C12380.7Semi standard non polar33892256
Imidazoleacetic acid riboside,1TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(CC(=O)O)=C2)[C@@H]1O2369.9Semi standard non polar33892256
Imidazoleacetic acid riboside,1TMS,isomer #4C[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N12322.1Semi standard non polar33892256
Imidazoleacetic acid riboside,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O2353.5Semi standard non polar33892256
Imidazoleacetic acid riboside,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O2367.0Semi standard non polar33892256
Imidazoleacetic acid riboside,2TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C2352.0Semi standard non polar33892256
Imidazoleacetic acid riboside,2TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(CC(=O)O)=C2)[C@@H]1O[Si](C)(C)C2355.6Semi standard non polar33892256
Imidazoleacetic acid riboside,2TMS,isomer #5C[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N12342.3Semi standard non polar33892256
Imidazoleacetic acid riboside,2TMS,isomer #6C[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N12331.1Semi standard non polar33892256
Imidazoleacetic acid riboside,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O2372.2Semi standard non polar33892256
Imidazoleacetic acid riboside,3TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C2355.4Semi standard non polar33892256
Imidazoleacetic acid riboside,3TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2337.8Semi standard non polar33892256
Imidazoleacetic acid riboside,3TMS,isomer #4C[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N12334.9Semi standard non polar33892256
Imidazoleacetic acid riboside,4TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2371.1Semi standard non polar33892256
Imidazoleacetic acid riboside,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O2629.2Semi standard non polar33892256
Imidazoleacetic acid riboside,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(CC(=O)O)=C12611.5Semi standard non polar33892256
Imidazoleacetic acid riboside,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(CC(=O)O)=C2)[C@@H]1O2615.6Semi standard non polar33892256
Imidazoleacetic acid riboside,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N12561.7Semi standard non polar33892256
Imidazoleacetic acid riboside,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O2806.6Semi standard non polar33892256
Imidazoleacetic acid riboside,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2843.3Semi standard non polar33892256
Imidazoleacetic acid riboside,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2830.1Semi standard non polar33892256
Imidazoleacetic acid riboside,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(CC(=O)O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C2824.7Semi standard non polar33892256
Imidazoleacetic acid riboside,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N12809.5Semi standard non polar33892256
Imidazoleacetic acid riboside,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N12804.4Semi standard non polar33892256
Imidazoleacetic acid riboside,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3024.9Semi standard non polar33892256
Imidazoleacetic acid riboside,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3016.3Semi standard non polar33892256
Imidazoleacetic acid riboside,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3034.0Semi standard non polar33892256
Imidazoleacetic acid riboside,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N13017.0Semi standard non polar33892256
Imidazoleacetic acid riboside,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(CC(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3209.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Imidazoleacetic acid riboside GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9420000000-7959b68020f3ef068c782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidazoleacetic acid riboside GC-MS (4 TMS) - 70eV, Positivesplash10-0pl9-7655930000-6b1eb646515d38c641122017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidazoleacetic acid riboside GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidazoleacetic acid riboside GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 10V, Positive-QTOFsplash10-0a6u-0970000000-3d8e5609d1b39e7b48012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 20V, Positive-QTOFsplash10-0a6r-0900000000-207d14b4f3f62f486e7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 40V, Positive-QTOFsplash10-004i-8900000000-9e8178d16dd80ec493762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 10V, Negative-QTOFsplash10-0a4i-0590000000-f3fa710ee357a2d741112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 20V, Negative-QTOFsplash10-004i-2920000000-69577a44e601ae9395602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 40V, Negative-QTOFsplash10-056r-8900000000-690bc05b5807ab94b7d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 10V, Negative-QTOFsplash10-0a4i-2890000000-e9f2aad1608ad01089752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 20V, Negative-QTOFsplash10-0a6r-8910000000-12c274c705c66cf2ef822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 40V, Negative-QTOFsplash10-0zi3-9400000000-49e960c72a7917a8555e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 10V, Positive-QTOFsplash10-0a4i-0690000000-7654298b3d60f23990752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 20V, Positive-QTOFsplash10-0a7i-3950000000-355655c064dd6d4aea3f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazoleacetic acid riboside 40V, Positive-QTOFsplash10-0a7i-8900000000-e721a8e65963c98f6a7c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022964
KNApSAcK IDNot Available
Chemspider ID389469
KEGG Compound IDC05131
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6626
PubChem Compound440569
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBaddiley, J.; Buchanan, J. G.; Hayes, D. H.; Smith, P. A. Synthesis of 1-b-D-ribofuranosyl-4(5)-glyoxalinylacetic acid, a metabolite of histamine. Journal of the Chemical Society (1958), 3743-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thomas B, Prell GD: Imidazoleacetic acid, a gamma-aminobutyric acid receptor agonist, can be formed in rat brain by oxidation of histamine. J Neurochem. 1995 Aug;65(2):818-26. [PubMed:7616240 ]