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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:36:37 UTC
Update Date2019-07-23 06:34:51 UTC
HMDB IDHMDB0041691
Secondary Accession Numbers
  • HMDB41691
Metabolite Identification
Common Name5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone
Description5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).
Structure
Data?1563863691
SynonymsNot Available
Chemical FormulaC11H12O5
Average Molecular Weight224.21
Monoisotopic Molecular Weight224.068473494
IUPAC Name5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
Traditional Name5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O
InChI Identifier
InChI=1S/C11H12O5/c12-8-4-6(5-9(13)11(8)15)3-7-1-2-10(14)16-7/h4-5,7,12-13,15H,1-3H2
InChI KeyCZVAQLJEUUFQCH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrogallols and derivatives. These are compounds containing a 1,2,3-trihydroxybenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct ParentPyrogallols and derivatives
Alternative Parents
Substituents
  • Pyrogallol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 Solubility1.94 g/LALOGPS
logP1.18ALOGPS
logP1.31ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.89ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.29 m³·mol⁻¹ChemAxon
Polarizability21.64 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbi-4900000000-aa407ce8b92827122435JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00us-4009100000-3c85a877af2785527a37JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0390000000-005c046b64fa400546eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-2920000000-3da2123cba34d8e561f8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9800000000-4d0ddda730f3f457928cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-ca50e6c2cd8c6aed9f93JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-2970000000-91fdf1beca5ad48fa42fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-7900000000-06a574a6947ca4bd6f67JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029854
KNApSAcK IDNot Available
Chemspider ID21233624
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44389277
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 6-{2,3-dihydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 6-{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphatedetails