ChemFOnt: Showing chemical card for Citramalic acid (CFc000000324)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:41 UTC

Chemfont ID

CFc000000324

Molecule Identification

Common Name

Citramalic acid

Definition

Citramalic acid, also known as 2-Methylmalic acid, is an analog of malic acid. The structure of citramalic acid is similar to the structure of malic acid except it has an extra CH3 group on position 2. It is also classified as a 2-hydroxydicarboxylic acid. Citramalic acid exists in two isomers, L-citramalic acid and D-citramalic acid. The L-isomer is more biologically relevant isomer. Citramalic acid is found in almost all living organisms from microbes to plants to humans although citramalate is primarily produced from bacteria. L-citramalic acid was first isolated from the peel of apples in 1954 (PMID: 13160011 ). It has also been isolated in wine and other ripening fruit (PMID: 13807713 ). Citramalic acid can inhibit the production of malic acid. Citramalic acid is also an important microbial metabolite and has been found to be a byproduct of Saccharomyces yeast species, as well as Propionibacterium acnes and Aspergillus niger (PMID: 31827810 ) (http://drweyrich.weyrich.com/labs/oat.html) (PMID: 7628083 ). Citramalic acid is a component of the C5-branched dibasic acid metabolism pathway. It can be broken down by the enzyme citramalate lyase, which converts citramalate to acetate and pyruvate. Citramalate synthase is an enzyme found in bacteria that synthesizes citramalic acid from acetyl-CoA, pyruvate and water. Citramalic acid may have a useful role in medical diagnoses. It has been found in the urine of two brothers with autistic features (PMID: 7628083 ). Citramalic acid can also be used as a urinary marker for gut dysbiosis (PMID: 31669633 ). Dysbiosis is a disorder of the bacterial flora of the human digestive tract. It is usually diagnosed clinically by direct detection of an abnormal pattern of the intestinal microbiota.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-2-Hydroxy-2-methylsuccinic acid	ChEBI
2-Hydroxy-2-methylbutanedioic acid	ChEBI
2-Hydroxy-2-methylsuccinic acid	ChEBI
2-Methylmalic acid	ChEBI
alpha-Hydroxypyrotartaric acid	ChEBI
Citramalic acids	ChEBI
(+-)-2-Hydroxy-2-methylsuccinate	Generator
2-Hydroxy-2-methylbutanedioate	Generator
2-Hydroxy-2-methylsuccinate	Generator
2-Methylmalate	Generator
a-Hydroxypyrotartarate	Generator
a-Hydroxypyrotartaric acid	Generator
alpha-Hydroxypyrotartarate	Generator
Α-hydroxypyrotartarate	Generator
Α-hydroxypyrotartaric acid	Generator
Citramalate	Generator
(b)-2-Methylmalate	HMDB
(b)-2-Methylmalic acid	HMDB
(b)-Citramalate	HMDB
(b)-Citramalic acid	HMDB
(R,S)-(b)-Citramalate	HMDB
(R,S)-(b)-Citramalic acid	HMDB
(R,S)-b-Methylmalate	HMDB
(R,S)-b-Methylmalic acid	HMDB
(R,S)-beta-Methylmalate	HMDB
(R,S)-beta-Methylmalic acid	HMDB
2-Deoxy-3-C-methyltetrarate	HMDB
2-Deoxy-3-C-methyltetraric acid	HMDB
2-Hydroxy-2-methyl-(b)-butanedioate	HMDB
2-Hydroxy-2-methyl-(b)-butanedioic acid	HMDB
2-Hydroxy-2-methyl-butanedioate	HMDB
2-Hydroxy-2-methyl-butanedioic acid	HMDB
2-Methyl-(b)-malate	HMDB
2-Methyl-(b)-malic acid	HMDB
DL-Citramalate	HMDB
DL-Citramalic acid	HMDB
Citramalate, (+-)-isomer	HMDB
Citramalate, (R)-isomer	HMDB
Citramalate, (S)-isomer	HMDB
alpha-Methylmalate	HMDB
(R)-2-Hydroxy-2-methylbutanedioate	HMDB
Citramalic acid	KEGG

Chemical Formula

C₅H₈O₅

Average Molecular Weight

148.114

Monoisotopic Molecular Weight

148.037173366

IUPAC Name

2-hydroxy-2-methylbutanedioic acid

Traditional Name

citramalate, (+-)-

CAS Registry Number

597-44-4

SMILES

CC(O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)

InChI Key

XFTRTWQBIOMVPK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxy carboxylic acid (CHEBI:15584 )
2-hydroxydicarboxylic acid (CHEBI:15584 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 22411374)

Cellular substructure

Cytoplasm (HMDB: HMDB0000426)
Cell membrane (HMDB: HMDB0000426)

Organelle

Adiposome (HMDB: HMDB0000426)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000426)

Source

Endogenous

Endogenous (HMDB: HMDB0000426)

Plant

Plant (HMDB: HMDB0000426)

Animal

Animal (HMDB: HMDB0000426)

Microbe

Microbe (HMDB: HMDB0000426)
Propionibacterium acnes (HMDB: HMDB0000426)

Exogenous

Food

Food (HMDB: HMDB0000426)

Fruit

Drupe

Sour cherry (FooDB: FOOD00146)

Exogenous (HMDB: HMDB0000426)

Saccharomyces cerevisiae (HMDB: HMDB0000426)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000426)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000426)

Lipid metabolism pathway (HMDB: HMDB0000426)

Biochemical process

Lipid transport (HMDB: HMDB0000426)

Role

Biological role

Energy source (HMDB: HMDB0000426)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	297 g/L	ALOGPS
logP	-0.91	ALOGPS
logP	-0.68	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.59 m³·mol⁻¹	ChemAxon
Polarizability	12.69 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