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Record Information
Version3.6
Creation Date2006-05-22 14:17:35 UTC
Update Date2016-05-18 21:40:43 UTC
HMDB IDHMDB02072
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Methoxyphenylacetic acid
Description4-Methoxyphenylacetic acid is a 4-O-Methylated catecholamine metabolite found in normal human urine, cerebrospinal fluid and brain tissue. (PMIDs 6511847, 4645252, 12416886).
Structure
Thumb
Synonyms
ValueSource
(4-Methoxyphenyl)acetic acidChEBI
2-(P-Anisyl)acetic acidChEBI
4-Methoxybenzeneacetic acidChEBI
Homoanisic acidChEBI
MOPAChEBI
P-Methoxy-alpha-toluic acidChEBI
P-Methoxyphenylacetic acidChEBI
(4-Methoxyphenyl)acetateGenerator
2-(4-Methoxyphenyl)acetateGenerator
2-(P-Anisyl)acetateGenerator
4-MethoxybenzeneacetateGenerator
HomoanisateGenerator
P-Methoxy-a-toluateGenerator
P-Methoxy-a-toluic acidGenerator
P-Methoxy-alpha-toluateGenerator
P-Methoxy-α-toluateGenerator
P-Methoxy-α-toluic acidGenerator
P-MethoxyphenylacetateGenerator
(4-Methoxy-phenyl)-acetateHMDB
(4-Methoxy-phenyl)-acetic acidHMDB
(P-Methoxyphenyl)acetateHMDB
(P-Methoxyphenyl)acetic acidHMDB
4-Methoxy phenylacetic acidHMDB
4-Methoxy-benzeneacetateHMDB
4-Methoxy-benzeneacetic acidHMDB
4-MethoxyphenylacetateHMDB
homo-P-Anisic acidHMDB
P-Methoxyphenyl-acetateHMDB
P-Methoxyphenyl-acetic acidHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(4-methoxyphenyl)acetic acid
Traditional Name4-methoxyphenylacetic acid
CAS Registry Number104-01-8
SMILES
COC1=CC=C(CC(O)=O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyInChIKey=NRPFNQUDKRYCNX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point87 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18 mg/mLNot Available
LogP1.42HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.43 mg/mLALOGPS
logP1.73ALOGPS
logP1.45ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.83 m3·mol-1ChemAxon
Polarizability16.86 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-9a07510e862a3a8fbc0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-4900000000-a51b42c5bcf30f73fa21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-09ddc34c57dd8f759d36View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.123 +/- 0.032 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.107 +/- 0.035 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.113 +/- 0.029 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.175 +/- 0.066 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.126 +/- 0.029 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.114 +/- 0.012 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.111 +/- 0.03 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.445 +/- 0.382 uMAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.073 +/- 0.046 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral leukoplakia (OLK) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022832
KNApSAcK IDNot Available
Chemspider ID7406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02072
Metagene LinkHMDB02072
METLIN ID6472
PubChem Compound7690
PDB IDNot Available
ChEBI ID55501
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [6511847 ]