ChemFOnt: Showing chemical card for (R)-2-Hydroxy-2-methylbutanedioic acid (CFc000333132)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:56 UTC

Chemfont ID

CFc000333132

Molecule Identification

Common Name

(R)-2-Hydroxy-2-methylbutanedioic acid

Definition

Constituent of apple peel. (R)-2-Hydroxy-2-methylbutanedioic acid is found in pomes.

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

6236-10-8

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

Not Available

Exogenous (HMDB: HMDB0000426)

Food

Fruit

Pome

Pomes (FooDB: FOOD00856)

Process

Not Available

Role

Not Available

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