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Record Information
Version3.6
Creation Date2006-08-24 12:35:05 UTC
Update Date2017-08-16 04:19:43 UTC
HMDB IDHMDB0004815
Secondary Accession Numbers
  • HMDB04815
Metabolite Identification
Common Name4-Hydroxy-3-methylbenzoic acid
Description4-Hydroxy-3-methylbenzoic acid is a normal organic acid identified in urine specimens from a healthy population. (PMID 8087979 ).
Structure
Thumb
Synonyms
ValueSource
4,3-Cresotic acidChEBI
4-Hydroxy-m-toluic acidChEBI
4,3-CresotateGenerator
4-Hydroxy-3-methylbenzoateGenerator
4-Hydroxy-m-toluateGenerator
3-Methyl-4-hydroxybenzoateHMDB
3-Methyl-4-hydroxybenzoic acidHMDB
4-Hydroxy-3-methyl-benzoateHMDB
4-Hydroxy-3-methyl-benzoic acidHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name4-hydroxy-3-methylbenzoic acid
Traditional Name4-hydroxy-3-methylbenzoic acid
CAS Registry Number499-76-3
SMILES
CC1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4,9H,1H3,(H,10,11)
InChI KeyLTFHNKUKQYVHDX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-cresol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mL at 100 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.52 mg/mLALOGPS
logP1.86ALOGPS
logP1.84ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.34 m3·mol-1ChemAxon
Polarizability15.01 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)splash10-0pb9-0900000000-7116c4f6bc6a16489f93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002f-9100000000-5cb5ac07c526f364ec47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00or-9000000000-48da170e5bf8545c76adView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified13.1 (3.6-54.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified7.5 (6.7-17.1) umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected and Quantified6.0 (0.9-28.6) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified4.3 (2.7-8.9) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified3.0 (1.3-9.7) umol/mmol creatinineAdolescent (13-18 years old)Both
    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 IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023425
    KNApSAcK IDNot Available
    Chemspider ID61446
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0004815
    METLIN IDNot Available
    PubChem Compound68138
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceKing, L. Carroll; McWhirter, Margaret; Barton, Daniel M. Reactions of acetophenols with iodine and pyridine and the preparation of hydroxybenzoic acids. Journal of the American Chemical Society (1945), 67 2089-92.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]