ChemFOnt: Showing chemical card for Mesaconic acid (CFc000000597)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:01 UTC

Chemfont ID

CFc000000597

Molecule Identification

Common Name

Mesaconic acid

Definition

Mesaconic acid, also known as 2-methylfumarate or citronic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‚Äòt Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-2-Methyl-2-butenedioic acid	ChEBI
(e)-Citraconic acid	ChEBI
2-Methylfumaric acid	ChEBI
Citronic acid	ChEBI
Methylfumaric acid	ChEBI
trans-1-Propene-1,2-dicarboxylic acid	ChEBI
trans-2-Methyl-2-butenedioic acid	ChEBI
2-Methylfumarate	Kegg
(e)-2-Methyl-2-butenedioate	Generator
(e)-Citraconate	Generator
Citronate	Generator
Methylfumarate	Generator
trans-1-Propene-1,2-dicarboxylate	Generator
trans-2-Methyl-2-butenedioate	Generator
Mesaconate	Generator
(Z)-2-Methyl-2-butenedioic acid	HMDB
Citraconic acid	HMDB
Citraconic acid, (e)-isomer	HMDB
Citraconic acid, ammonium salt	HMDB
Citraconic acid, calcium salt	HMDB
Citraconic acid, sodium salt	HMDB
Methylmaleic acid	HMDB
Monomethylfumarate	HMDB
(2E)-2-Methyl-2-butenedioate	HMDB
(2E)-2-Methyl-2-butenedioic acid	HMDB

Chemical Formula

C₅H₆O₄

Average Molecular Weight

130.0987

Monoisotopic Molecular Weight

130.02660868

IUPAC Name

(2E)-2-methylbut-2-enedioic acid

Traditional Name

mesaconic acid

CAS Registry Number

498-24-8

SMILES

C\C(=C/C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+

InChI Key

HNEGQIOMVPPMNR-NSCUHMNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:16600 )
Dicarboxylic acids (LMFA01170116 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000749)

Extracellular (HMDB: HMDB0000749)
Membrane (HMDB: HMDB0000749)

Source

Exogenous

Exogenous (HMDB: HMDB0000749)

Endogenous

Endogenous (HMDB: HMDB0000749)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	15.9 g/L	ALOGPS
logP	0.21	ALOGPS
logP	0.35	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.96 m³·mol⁻¹	ChemAxon
Polarizability	11.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon