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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:39:25 UTC
Update Date2019-07-23 06:14:35 UTC
HMDB IDHMDB0033884
Secondary Accession Numbers
  • HMDB33884
Metabolite Identification
Common NameGravolenic acid
DescriptionGravolenic acid, also known as gravolenate, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Gravolenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gravolenic acid has been detected, but not quantified in, herbs and spices. This could make gravolenic acid a potential biomarker for the consumption of these foods.
Structure
Data?1563862475
Synonyms
ValueSource
GravolenateGenerator
(2Z)-3-[4,5-Dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoateGenerator
Chemical FormulaC14H16O6
Average Molecular Weight280.2732
Monoisotopic Molecular Weight280.094688244
IUPAC Name(2Z)-3-[4,5-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoic acid
Traditional Name(2Z)-3-[4,5-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoic acid
CAS Registry Number13781-46-9
SMILES
CC(C)(O)C1CC2=C(O)C(O)=CC(\C=C/C(O)=O)=C2O1
InChI Identifier
InChI=1S/C14H16O6/c1-14(2,19)10-6-8-12(18)9(15)5-7(13(8)20-10)3-4-11(16)17/h3-5,10,15,18-19H,6H2,1-2H3,(H,16,17)/b4-3-
InChI KeyDABSIZUNYJTFDJ-ARJAWSKDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Coumaran
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point194 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP1.4ALOGPS
logP1.48ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.81 m³·mol⁻¹ChemAxon
Polarizability28.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bt9-7190000000-73c954728f9772071d7aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ll0-7590540000-6a00bc06d5a6a29f9804Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0090000000-3bc89561c66281086000Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0jca-1090000000-eff4b3e0910441ef70c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2920000000-e42346980ae05e797f8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-c469059fe0dfb8bba15cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-e8d0adb8eaea8699e3ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2920000000-d6157fc2a55627231cb2Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012077
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751501
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .