Showing Compound Card for Homovanillic acid (CDB006334)

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Record Information
Version1.0
Created at2020-09-11 15:49:28 UTC
Updated at2022-12-13 23:36:27 UTC
CannabisDB IDCDB006334
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHomovanillic acid
DescriptionHomovanillic acid, also known as vanillacetate or homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Homovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Homovanillic acid exists in all living species, ranging from bacteria to humans. Within humans, homovanillic acid participates in a number of enzymatic reactions. In particular, homovanillic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxybenzeneacetic acid and guaiacol through the action of the enzyme catechol O-methyltransferase. In addition, homovanillic acid can be biosynthesized from homovanillin; which is mediated by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. In humans, homovanillic acid is involved in disulfiram action pathway. Outside of the human body, Homovanillic acid is found, on average, in the highest concentration within olives and beers. Homovanillic acid has also been detected, but not quantified in, avocado and milk (cow). This could make homovanillic acid a potential biomarker for the consumption of these foods. Homovanillic acid is a potentially toxic compound. Homovanillic acid, with regard to humans, has been found to be associated with several diseases such as major depressive disorder, autism, hypothyroidism, and perillyl alcohol administration for cancer treatment; homovanillic acid has also been linked to the inborn metabolic disorder phenylketonuria.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4-Hydroxy-3-methoxyphenyl)acetic acidChEBI
3-Methoxy-4-hydroxyphenylacetateChEBI
3-Methoxy-4-hydroxyphenylacetic acidChEBI
4-Hydroxy-3-methoxybenzeneacetic acidChEBI
HVAChEBI
Vanillacetic acidChEBI
(4-Hydroxy-3-methoxyphenyl)acetateGenerator
4-Hydroxy-3-methoxybenzeneacetateGenerator
VanillacetateGenerator
HomovanillateGenerator
3-Methoxy-4-hydroxy-phenylacetic acidHMDB
4-Hydroxy 3-methoxyphenylacetic acidHMDB
4-Hydroxy-3-methoxyphenylacetic acidHMDB
HomovanilateHMDB
Homovanilic acidHMDB
Homovanillinic acidHMDB
VanilacetateHMDB
Vanilacetic acidHMDB
3 Methoxy 4 hydroxyphenylacetic acidHMDB
Acid, 3-methoxy-4-hydroxyphenylaceticHMDB
Acid, 4-hydroxy-3-methoxyphenylaceticHMDB
4 Hydroxy 3 methoxyphenylacetic acidHMDB
Acid, homovanillicHMDB
3'-Methoxy-4'-hydroxyphenylacetic acidHMDB
3’-methoxy-4’-hydroxyphenylacetic acidHMDB
4'-Hydroxy-3'-methoxy-phenylacetic acidHMDB
2-(4-Hydroxy-3-methoxyphenyl)acetic acidHMDB
4'-Hydroxy-3'-methoxyphenylacetic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Namehomovanillic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(CC(O)=O)=CC=C1O
InChI Identifier
InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChI KeyQRMZSPFSDQBLIX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
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
logP1.02ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.81 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-b8c848b70c066282b36f2014-09-20View Spectrum
GC-MSHomovanillic acid, non-derivatized, GC-MS Spectrumsplash10-056r-1962000000-4f8e427392aa8e136095Spectrum
GC-MSHomovanillic acid, 2 TMS, GC-MS Spectrumsplash10-056r-2972000000-f53a7b3ac40c099e3c99Spectrum
GC-MSHomovanillic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9800000000-def178a40b9d8cc16724Spectrum
GC-MSHomovanillic acid, non-derivatized, GC-MS Spectrumsplash10-06vi-0596000000-729a4b24107b98261cb2Spectrum
GC-MSHomovanillic acid, non-derivatized, GC-MS Spectrumsplash10-056r-1962000000-4f8e427392aa8e136095Spectrum
GC-MSHomovanillic acid, non-derivatized, GC-MS Spectrumsplash10-056r-2972000000-f53a7b3ac40c099e3c99Spectrum
GC-MSHomovanillic acid, non-derivatized, GC-MS Spectrumsplash10-056r-1962000000-24557ef3db49c59cd5ddSpectrum
Predicted GC-MSHomovanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1900000000-cb0e3eb7a6d9e785a2f8Spectrum
Predicted GC-MSHomovanillic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w0-9352000000-0e2f11bc503dd5ce6345Spectrum
Predicted GC-MSHomovanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomovanillic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomovanillic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomovanillic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomovanillic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomovanillic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-994a78c607c1b6a724d22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00fr-4900000000-ca5ef14a72dcdf3cf9fe2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9700000000-44f2784ec5407e93ea572012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0019-0900000000-aafe8aee1cf8c42b941a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-1900000000-313fe6eb451badd5c0522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0609-6900000000-11aa4fb169e782205ea32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-9200000000-637a59b417fe2b2e7f582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-7b87b58730add4511c8a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0019-0900000000-aafe8aee1cf8c42b941a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-313fe6eb451badd5c0522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0609-6900000000-11aa4fb169e782205ea32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9200000000-1bc951858c2e658a79af2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-7b87b58730add4511c8a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0900000000-0c3c4c703b4b9743a5212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0900000000-a5e048e5e58ed8e57ecd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0079-0900000000-35fbf40336719c96dd3d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-b408942abbf2cafac06e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-39dd2b8775ad5c5ec2f02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-4900000000-c9fd7643f48c0e43dc872021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-57e5685e37a2d70f9ab42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-b8470b9851db4df96b612015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-3900000000-2690d7c586d4f7c3dccf2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-713f0600845faa67fec32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-0900000000-30a79a8a4d5cf0ffc8642015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-2900000000-6f967f9e7f7117a9d1e42015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.000109 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.000689 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00126 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0000678 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.000314 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.000173 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000118
DrugBank IDNot Available
Phenol Explorer Compound ID574
FoodDB IDFDB001783
KNApSAcK IDC00029504
Chemspider ID1675
KEGG Compound IDC05582
BioCyc IDCPD-7651
BiGG ID46066
Wikipedia LinkHomovanillic_acid
METLIN ID971
PubChem Compound1738
PDB IDNot Available
ChEBI ID545959
References
General ReferencesNot Available