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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 05:40:33 UTC
Update Date2021-09-23 05:40:33 UTC
HMDB IDHMDB0302011
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid
Description3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid, also known as amorfrutin a, is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid can be found in pigeon pea, which makes 3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
Amorfrutin aMeSH
3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylateGenerator
Chemical FormulaC21H24O4
Average Molecular Weight340.4129
Monoisotopic Molecular Weight340.167459256
IUPAC Name2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid
Traditional Name2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(CCC2=CC=CC=C2)=C(C(O)=O)C(O)=C1CC=C(C)C
InChI Identifier
InChI=1S/C21H24O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)
InChI KeyCTNFTPUIYFUXBE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • P-methoxybenzoic acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP4.37ALOGPS
logP6.08ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.34 m³·mol⁻¹ChemAxon
Polarizability37.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+184.90532859911
AllCCS[M+H-H2O]+181.66532859911
AllCCS[M+Na]+188.76832859911
AllCCS[M+NH4]+187.90632859911
AllCCS[M-H]-185.36232859911
AllCCS[M+Na-2H]-185.35632859911
AllCCS[M+HCOO]-185.50632859911
DeepCCS[M+H]+177.6530932474
DeepCCS[M-H]-175.25530932474
DeepCCS[M-2H]-209.58430932474
DeepCCS[M+Na]+184.95430932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 10V, Positive-QTOFsplash10-0006-1059000000-14419dfdc3805108af482016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 20V, Positive-QTOFsplash10-0007-4192000000-c214a6f223967ae06efc2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 40V, Positive-QTOFsplash10-0fto-7390000000-2da3d8024dfae0ab516d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 10V, Negative-QTOFsplash10-000j-0069000000-62ed9d6d0ace42a422142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 20V, Negative-QTOFsplash10-002b-0092000000-dc89de4ca2aaebb9307a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 40V, Negative-QTOFsplash10-004i-2290000000-11d50fef8433616ffa6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 10V, Positive-QTOFsplash10-01bl-0094000000-a6e478f8da9ba40f41012021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 20V, Positive-QTOFsplash10-014i-0092000000-d6cf84ffef5d5aa9b21a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 40V, Positive-QTOFsplash10-0a4l-9881000000-21aecb7e20c41f460dc92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 10V, Negative-QTOFsplash10-000i-0019000000-1115664bb0ab2f7a04422021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 20V, Negative-QTOFsplash10-03ds-0093000000-e29868f6b209be115bf22021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid 40V, Negative-QTOFsplash10-000i-0179000000-14dbd6354a0192e065902021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB001743
KNApSAcK IDC00015437
Chemspider ID16430153
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17950432
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available