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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-08 21:43:03 UTC
Update Date2019-01-11 19:37:35 UTC
HMDB IDHMDB0029226
Secondary Accession Numbers
  • HMDB29226
Metabolite Identification
Common Name5'-(3'-Methoxy-4'-hydroxyphenyl)-gamma-valerolactone
Description5'-(3'-methoxy-4'-hydroxyphenyl)-gamma-valerolactone is a cocoa metabolite from gut microflora. It is found in urine.
Structure
Data?1547235455
Synonyms
ValueSource
3-Methoxy-4-hydroxyphenylvalerolactoneHMDB
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name5-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Name5-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(CC2CCC(=O)O2)=C1
InChI Identifier
InChI=1S/C12H14O4/c1-15-11-7-8(2-4-10(11)13)6-9-3-5-12(14)16-9/h2,4,7,9,13H,3,5-6H2,1H3
InChI KeyGCIFEQYZDROELP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Gamma butyrolactone
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

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 Solubility0.76 g/LALOGPS
logP1.75ALOGPS
logP1.76ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.79 m³·mol⁻¹ChemAxon
Polarizability22.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-3900000000-101e5c2c33e484d9f010View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-4190000000-000515bca2b1d6a2ca9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0490000000-3413b4e3e517e00cfbf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022j-2920000000-94eb508dd7b5dbe4b3adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9600000000-8b60dc51ce2c4af7d617View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-fdbff165badbfda7678eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-3890000000-d79c916c180c816dc61aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9700000000-2b53eaeae51e5ee367a5View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 979 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Diabetes mellitus
details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Llorach R, Urpi-Sarda M, Tulipani S, Garcia-Aloy M, Monagas M, Andres-Lacueva C: Metabolomic fingerprint in patients at high risk of cardiovascular disease by cocoa intervention. Mol Nutr Food Res. 2013 Jun;57(6):962-73. doi: 10.1002/mnfr.201200736. Epub 2013 May 2. [PubMed:23637065 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID979
FoodDB IDFDB029858
KNApSAcK IDNot Available
Chemspider ID2293832
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3028410
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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'-Methoxy-4'-hydroxyphenyl)-gamma-valerolactone → 3,4,5-trihydroxy-6-{2-methoxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-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'-Methoxy-4'-hydroxyphenyl)-gamma-valerolactone → {2-methoxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic aciddetails