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Record Information
Version3.6
Creation Date2006-02-23 11:14:42 UTC
Update Date2016-02-11 01:05:03 UTC
HMDB IDHMDB01868
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Methoxysalicylic acid
Description5-Methoxysalicylic acid is an aminosalicylic acid that has been found to. enhance intestinal absorption of insulin in rats and insulin uptake into human red blood cells (PMID 6319944 ).
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-5-methoxybenzoateHMDB
2-Hydroxy-5-methoxybenzoic acidHMDB
5-Methoxy-2-hydroxybenzoateHMDB
5-Methoxy-2-hydroxybenzoic acidHMDB
5-MethoxysalicylateHMDB
6-Hydroxy-m-anisateHMDB
6-Hydroxy-m-anisic acidHMDB
6-Methoxy-m-anisateHMDB
6-Methoxy-m-anisic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-5-methoxybenzoic acid
Traditional Name5-methoxysalicylic acid
CAS Registry Number2612-02-4
SMILES
COC1=CC(C(O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyInChIKey=IZZIWIAOVZOBLF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Methoxyphenol
  • Hydroxybenzoic acid
  • Benzoic acid
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.38 mg/mLALOGPS
logP1.85ALOGPS
logP1.82ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m3·mol-1ChemAxon
Polarizability15.8 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)splash10-02t9-2900000000-eca7c3623a7975e733d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-5900000000-5aaba4f93b26c36dfcb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fvl-9100000000-94c4137aab8bf06f3617View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negativesplash10-0udi-0901000000-077381dba9d80706a097View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-0fri-0930000000-4e24b1261f33fba704e2View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Red Blood Cell
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified8.294 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
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 IDFDB011959
KNApSAcK IDNot Available
Chemspider ID68296
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01868
Metagene LinkHMDB01868
METLIN ID4164
PubChem Compound75787
PDB IDNot Available
ChEBI ID545920
References
Synthesis ReferenceNagasawa, Masaaki; Nishioka, Hiroyasu; Suzuki, Takanori; Nagano, Eiichi; Ishii, Katsuyuki; Nakao, Ryu. Preparation of salicylic acids from 2-methoxybenzoic acids. Jpn. Kokai Tokkyo Koho (2000), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nishihata T, Higuchi T, Kamada A: Possible mechanism of uptake for several compounds in ionized form through human erythrocyte membrane. Life Sci. 1984 Jan 30;34(5):427-36. [6694531 ]
  2. Nishihata T, Higuchi T, Kamada A: Salicylate-promoted permeation of cefoxitin, insulin and phenylalanine across red cell membrane. Possible mechanism. Life Sci. 1984 Jan 30;34(5):437-45. [6319944 ]