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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2018-10-12 16:05:50 UTC
Update Date2019-04-01 19:20:37 UTC
HMDB IDHMDB0240294
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-O-Methylascorbic acid
Description2-O-Methylascorbic acid (2-O-MA) is a derivative of vitamin C (ascorbic acid). The enzyme catechol-O-methyltransferase catalyzes the methylation of L-ascorbic acid into 2-O-methylascorbic acid (PMID: 7129800 ). 2-O-Methylascorbic acid belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 2-O-Methylascorbic acid has been identified in urine and was found to be higher in older women than in younger women (PMID: 28813537 ).
Structure
Data?1551940024
Synonyms
ValueSource
2-O-Methyl-L-ascorbic acidHMDB
2-Methyl-L-ascorbic acidHMDB
2-Methylascorbic acidHMDB
2-O-Methylascorbic acidHMDB
2-O-MAHMDB
Chemical FormulaC7H10O6
Average Molecular Weight190.151
Monoisotopic Molecular Weight190.047738042
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-methoxy-2,5-dihydrofuran-2-one
Traditional Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-methoxy-5H-furan-2-one
CAS Registry Number17860-87-6
SMILES
[H][C@@]1(OC(=O)C(OC)=C1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C7H10O6/c1-12-6-4(10)5(3(9)2-8)13-7(6)11/h3,5,8-10H,2H2,1H3/t3-,5+/m0/s1
InChI KeyJBXPKMHATRSERD-WVZVXSGGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-1.8ChemAxon
logS0.09ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.78 m³·mol⁻¹ChemAxon
Polarizability16.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54726398
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bowers-Komro DM, McCormick DB, King GA, Sweeny JG, Iacobucci GA: Confirmation of 2-O-methyl ascorbic acid as the product from the enzymatic methylation of L-ascorbic acid by catechol-O-methyltransferase. Int J Vitam Nutr Res. 1982;52(2):186-93. [PubMed:7129800 ]
  2. Rist MJ, Roth A, Frommherz L, Weinert CH, Kruger R, Merz B, Bunzel D, Mack C, Egert B, Bub A, Gorling B, Tzvetkova P, Luy B, Hoffmann I, Kulling SE, Watzl B: Metabolite patterns predicting sex and age in participants of the Karlsruhe Metabolomics and Nutrition (KarMeN) study. PLoS One. 2017 Aug 16;12(8):e0183228. doi: 10.1371/journal.pone.0183228. eCollection 2017. [PubMed:28813537 ]