Showing metabocard for 5-Methoxysalicylic acid (BMDB0001868)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:25 UTC
Update Date2020-05-11 19:59:11 UTC
BMDB IDBMDB0001868
Secondary Accession Numbers
  • BMDB01868
Metabolite Identification
Common Name5-Methoxysalicylic acid
Description5-Methoxysalicylic acid, also known as 5-meosa or 5-O-methyl gentisic acid, 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. Based on a literature review a significant number of articles have been published on 5-Methoxysalicylic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-MeOSAChEBI
5-Methoxy-2-hydroxybenzoic acidChEBI
5-O-Methyl gentisic acidChEBI
6-Hydroxy-m-anisic acidChEBI
Acid5-methoxysalicylicChEBI
5-Methoxy-2-hydroxybenzoateGenerator
5-O-Methyl gentisateGenerator
6-Hydroxy-m-anisateGenerator
5-MethoxysalicylateGenerator
2-Hydroxy-5-methoxybenzoateHMDB, Generator
2-Hydroxy-5-methoxybenzoic acidHMDB
6-Methoxy-m-anisateHMDB
6-Methoxy-m-anisic acidHMDB
5-Methoxysalicylic acid, sodium saltMeSH, HMDB
5-Methoxysalicylic acidMeSH
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 KeyIZZIWIAOVZOBLF-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Hydroxybenzoic acid
  • Methoxyphenol
  • 4-alkoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not 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
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-0v4i-1900000000-1e109eb0ee8ae327f133View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0092-3290000000-b2c04fbea10000b9034eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0900000000-e2d69678bf5361774dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0pvi-0900000000-46471751a79101b1fd39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0900000000-e2d69678bf5361774dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0pvi-0900000000-46471751a79101b1fd39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-4fe7b9af6ce0405606a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-e2d69678bf5361774dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0fdk-9700000000-dcbbb81e035f6deb9148View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-844a327be60247da81aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9200000000-29a841e2d36df5762a0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-a9825a2a16be2ec1b6d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0900000000-7ee52209d923d99f69efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-d2f3d14888f1a31ec2c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c1-9300000000-1ba0741166e840d38463View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-2c570bf0fdb5915da23aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0900000000-77290f37ff3e5699255aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-b642574365d90b34c12cView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, 5%_DMSO, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Erythrocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001868
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011959
KNApSAcK IDC00055625
Chemspider ID68296
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Methoxysalicylic_acid
METLIN ID4164
PubChem Compound75787
PDB IDNot Available
ChEBI ID89830
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)Not Available
General ReferencesNot Available