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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:51 UTC
HMDB IDHMDB01101
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Anisic acid
DescriptionAnisic acid is a phenolic acid, an organic molecule commonly found in anis-seed, a common food spice. Anisic acid is occasionally found in human biofluids. Anisic acid has been characterized as a classical non-competitive inhibitor of the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA), and the hydroxylation of L-tyrosine catalyzed by tyrosinase (EC 1.14.18.1). Additionally, anisic acid is a metabolite of aniracetam, a cognition enhancer. (PMID: 14577637 , 6480763 , 6511847 , 11597608 ).
Structure
Thumb
Synonyms
ValueSource
4-Methoxybenzoic acidKegg
4-Anisic acidKegg
4-MethoxybenzoateGenerator
P-AnisateGenerator
4-AnisateGenerator
Anisic acidHMDB
Draconic acidHMDB
P-MethoxybenzoateHMDB
P-Methoxybenzoic acidHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name4-methoxybenzoic acid
Traditional NameP-anisic acid
CAS Registry Number100-09-4
SMILES
COC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyInChIKey=ZEYHEAKUIGZSGI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • Benzoic acid
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 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 but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.53 mg/mL at 37 °CNot Available
LogP1.96HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.0 mg/mLALOGPS
logP1.63ALOGPS
logP1.47ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.78 m3·mol-1ChemAxon
Polarizability14.99 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pb9-0900000000-e12fd27c6bd5db5e2279View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0a041f6a0f7956c7a3b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6bad7ffd64345511fe82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-0udr-3900000000-47cdda0bd47b983d915cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-2900000000-914fa5e9764ecaca52beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-8900000000-ff833ddec48810872135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-73a2bb654df643c39008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-79c889c668d83b893177View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-a33773d623f5deb358bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID425
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010587
KNApSAcK IDC00029536
Chemspider ID10181338
KEGG Compound IDC02519
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methoxybenzoic acid
NuGOwiki LinkHMDB01101
Metagene LinkHMDB01101
METLIN IDNot Available
PubChem Compound7478
PDB IDANN
ChEBI ID40813
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 ]
  2. Thoma H, Reiner J, Spiteller G: Profiles of strongly polar and less polar acids obtained from human blood, plasma and serum by two-step ultrafiltration. J Chromatogr. 1984 Jul 13;309(1):17-32. [6480763 ]
  3. Kubo I, Chen QX, Nihei K, Calderon JS, Cespedes CL: Tyrosinase inhibition kinetics of anisic acid. Z Naturforsch C. 2003 Sep-Oct;58(9-10):713-8. [14577637 ]
  4. Shirane M, Nakamura K: Aniracetam enhances cortical dopamine and serotonin release via cholinergic and glutamatergic mechanisms in SHRSP. Brain Res. 2001 Oct 19;916(1-2):211-21. [11597608 ]