ChemFOnt: Showing chemical card for 2-O-Methylascorbic acid (CFc000220557)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:44 UTC

Chemfont ID

CFc000220557

Molecule Identification

Common Name

2-O-Methylascorbic acid

Definition

2-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-O-Methylascorbate	Generator
2-O-Methyl-L-ascorbic acid	HMDB
2-Methyl-L-ascorbic acid	HMDB
2-Methylascorbic acid	HMDB
2-O-MA	HMDB
2-O-Methylascorbic acid	HMDB

Chemical Formula

C₇H₁₀O₆

Average Molecular Weight

190.151

Monoisotopic Molecular Weight

190.047738042

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 Number

17860-87-6

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 Key

JBXPKMHATRSERD-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Urine (PMID: 28813537)

Source

Exogenous

Exogenous (HMDB: HMDB0240294)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	237 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.8	ChemAxon
logS	0.09	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	41.78 m³·mol⁻¹	ChemAxon
Polarizability	16.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240294

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24688154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54726398

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-O-Methylascorbic acid (CFc000220557)

MOL for CFc000220557 (2-O-Methylascorbic acid)

3D MOL for CFc000220557 (2-O-Methylascorbic acid)

3D SDF for CFc000220557 (2-O-Methylascorbic acid)

3D-SDF for CFc000220557 (2-O-Methylascorbic acid)

PDB for CFc000220557 (2-O-Methylascorbic acid)

3D PDB for CFc000220557 (2-O-Methylascorbic acid)

SMILES for CFc000220557 (2-O-Methylascorbic acid)

INCHI for CFc000220557 (2-O-Methylascorbic acid)

Structure for CFc000220557 (2-O-Methylascorbic acid)

3D Structure for CFc000220557 (2-O-Methylascorbic acid)