ChemFOnt: Showing chemical card for 2-Methylcitric acid (CFc000000278)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:38 UTC

Chemfont ID

CFc000000278

Molecule Identification

Common Name

2-Methylcitric acid

Definition

Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000 , 232050 ), methylmalonic aciduria (MMA; OMIM 251000 , 251120 ) and multiple carboxylase deficiency (OMIM 253260 , 253270 ), which are inherited disorders. MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine (PMID: 17295121 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-1,2,3-butanetricarboxylic acid	ChEBI
2-Hydroxy-1,2,3-butanetricarboxylate	Generator
2-Methylcitrate	Generator
(2S,3S)-2-Methylcitrate	HMDB
2-Hydroxybutane-1,2,3-tricarboxylate	HMDB
2-Hydroxybutane-1,2,3-tricarboxylic acid	HMDB
2-Methylcitric acid, 3H-labeled	HMDB
3-Carboxy-3-hydroxy-2-methylpentanedioic acid	HMDB
Methylcitric acid	HMDB

Chemical Formula

C₇H₁₀O₇

Average Molecular Weight

206.1501

Monoisotopic Molecular Weight

206.042652674

IUPAC Name

2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid

Traditional Name

methylcitric acid

CAS Registry Number

6061-96-7

SMILES

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

InChI Identifier

InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)

InChI Key

YNOXCRMFGMSKIJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:30835 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12113988)
Cerebrospinal Fluid (CSF) (PMID: 8345822)
Cerebrospinal fluid (HMDB: HMDB0000379)

Organ

Placenta (HMDB: HMDB0000379)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 26848182)

Cellular substructure

Extracellular (HMDB: HMDB0000379)
Cytoplasm (HMDB: HMDB0000379)

Source

Endogenous

Endogenous (HMDB: HMDB0000379)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Propionic Acidemia (HMDB: HMDB0000379)
Methylmalonic Aciduria Due to Cobalamin-Related Disorders (HMDB: HMDB0000379)

Metabolic pathway

Propanoate Metabolism (PathBank: SMP0121322)

Role

Industrial application

Pharmaceutical industry

Biomarker

Biotinidase deficiency (MarkerDB: MDB00000155)
Propionic acidemia (MarkerDB: MDB00000155)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	175 g/L	ALOGPS
logP	-0.89	ALOGPS
logP	-0.78	ChemAxon
logS	-0.07	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.2 m³·mol⁻¹	ChemAxon
Polarizability	17.21 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

External Links

HMDB ID

HMDB0000379

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021997

KNApSAcK ID

Not Available

Chemspider ID

500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

39369

Wikipedia Link

Not Available

METLIN ID

5368

PubChem Compound

515

PDB ID

Not Available

ChEBI ID

30835

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander. Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain. PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007101866 A2 20070913 CAN 147:363646 AN 2007:1033111

Showing chemical card for 2-Methylcitric acid (CFc000000278)

MOL for CFc000000278 (2-Methylcitric acid)

3D MOL for CFc000000278 (2-Methylcitric acid)

3D SDF for CFc000000278 (2-Methylcitric acid)

3D-SDF for CFc000000278 (2-Methylcitric acid)

PDB for CFc000000278 (2-Methylcitric acid)

3D PDB for CFc000000278 (2-Methylcitric acid)

SMILES for CFc000000278 (2-Methylcitric acid)

INCHI for CFc000000278 (2-Methylcitric acid)

Structure for CFc000000278 (2-Methylcitric acid)

3D Structure for CFc000000278 (2-Methylcitric acid)