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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-04-09 21:17:08 UTC
Update Date2017-10-23 19:15:36 UTC
HMDB IDHMDB0059973
Secondary Accession Numbers
  • HMDB59973
Metabolite Identification
Common Name4-Hydroxy-5-(3',5'-dihydroxyphenyl)-valeric acid-O-glucuronide
Description4-Hydroxy-5-(3',5'-dihydroxyphenyl)-valeric acid-O-glucuronide is a conjugate of 4-hydroxy-5-(3',5'-dihydroxyphenyl)-valeric acid and glucuronide. A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H22O11
Average Molecular Weight402.35
Monoisotopic Molecular Weight402.116211546
IUPAC Name(2S,3S,4S,5R,6S)-6-{[5-(3,5-dihydroxyphenyl)-4-hydroxypentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[5-(3,5-dihydroxyphenyl)-4-hydroxypentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)CC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C17H22O11/c18-8(3-7-4-9(19)6-10(20)5-7)1-2-11(21)27-17-14(24)12(22)13(23)15(28-17)16(25)26/h4-6,8,12-15,17-20,22-24H,1-3H2,(H,25,26)/t8?,12-,13-,14+,15-,17+/m0/s1
InChI KeyCOBSRKLPDWFDCG-AHLSELSJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Hexose monosaccharide
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Pyran
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.04 g/LALOGPS
logP-0.49ALOGPS
logP-1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area194.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity89.1 m³·mol⁻¹ChemAxon
Polarizability38.49 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05br-9723000000-5d6ac6679b4a97c59555View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-05di-8232219000-9b19e239e235f462c865View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0495100000-b59f63012b1e7c4e25e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2961000000-520983c99507afe3be38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-8940000000-f0f18bbec4f2c7bafe98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0392200000-946695701749134dd5bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-3982000000-6831a8e9e8f50770d30cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9840000000-0434790464aad65e1bb6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)Both
    Diabetes mellitus
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem CompoundNot Available
    PDB IDNot Available
    ChEBI ID88688
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]