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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:51 UTC
Update Date2018-05-19 23:11:00 UTC
HMDB IDHMDB0059969
Secondary Accession Numbers
  • HMDB59969
Metabolite Identification
Common Name3-Methoxyphenylacetic acid
Description3-Methoxyphenylacetic acid, also known as m-Methoxyphenylacetic acid (m-OMePAA), a derivative of m-hydroxyphenylacetic acid (m-OHPAA) having the same chemical composition as that of the phytotoxic compound produced in culture by Rhizoctonia solani, a fungal pathogen of soybean. That phytotoxic compound reduced growth and symbiotic N2-fixation activity of Tracy soybeans in soil. The data indicate that phytotoxic compounds of R. solani are involved in nodule impairment and reduced N2-fixation in soybean (R. G. Orellana, and N. B. Mandava (1983) m-Hydroxyphenylacetic and m-Methoxyphenylacetic Acids of Rhizoctonia solani: Their Effect on Specific Root-Nodule Activity and Histopathology in Soybean. Journal of Phytopathology. Volume 107, Issue 2, pages 159167, June 1983).
Structure
Thumb
Synonyms
ValueSource
P-Methoxyphenylacetic acidMeSH
3-Methoxyphenylacetic acid, potassium saltMeSH
3-Methoxybenzeneacetic acidCAS
(3-Methoxyphenyl)acetic acidCAS
(m-Methoxyphenyl)acetic acidCAS
2-(3-Methoxyphenyl)acetic acidCAS
[3-(Methyloxy)phenyl]acetic acidCAS
m-Anisylacetic acidCAS
m-Methoxyphenylacetic acidHMDB
m-OMePAAHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(3-methoxyphenyl)acetic acid
Traditional NameM-methoxyphenylacetic acid
CAS Registry Number1798-09-0
SMILES
COC1=CC=CC(CC(O)=O)=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-8-4-2-3-7(5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyLEGPZHPSIPPYIO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

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 Solubility1.67 g/LALOGPS
logP1.71ALOGPS
logP1.45ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.83 m³·mol⁻¹ChemAxon
Polarizability16.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-ab5cfb2e84f1849fe9c7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9610000000-40ed49ec5775c011d1ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-dd75ebae080e8172f70bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-ce68fde7e48600c77582View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c03-9500000000-ab4452ccbe5b1d0e665eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-8f48d3c142877d5fc587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-1900000000-a45ae9a8435678aa41dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9500000000-2f74e68963c2c6c1c406View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.549 +/- 0.125 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15719
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]