ContaminantDB: Citramalic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:08:31 UTC

Update Date

2016-11-09 01:17:19 UTC

Accession Number

CHEM021623

Identification

Common Name

Citramalic acid

Class

Small Molecule

Description

A 2-hydroxydicarboxylic acid that is malic acid (hydroxysuccinic acid) in which the hydrogen at position 2 is substituted by a methyl group.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical 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 Mass

148.114 g/mol

Monoisotopic Mass

148.037 g/mol

CAS Registry Number

597-44-4

IUPAC Name

2-hydroxy-2-methylbutanedioic acid

Traditional Name

citramalate, (+-)-

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9200000000-d88cf81bb63b8badd74d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00gs-8492000000-d1c8fb9235f1de536d15	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000j-7900000000-efbe2adf2c82decc64a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-052u-9000000000-3754186783f820cbff7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052o-9000000000-0656e8e194378442727f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-2900000000-be1cc6b0ea685f5d7ac2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-002r-8900000000-7dd192ed79cd2d306ea5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9500000000-c96a62314140c10f1245	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-0002-2900000000-716fb416386753113137	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-20ae5f1dfa6847e56e0d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-4bc688d98054e464cf07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4r-9000000000-61294657ce4e2d5d6d05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9400000000-d027e4da9369388ea3c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e7930822f64c0c43d7c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9500000000-2e922f07663d3c399240	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9400000000-b372db83cd99e22fb0ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-093483f4bf2d387fa405	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001a-5900000000-437d36fe16a8d6f79c68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9200000000-6aed3a8e654948bbd5e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-31c6a41b79f5b68fa431	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uds-4900000000-0d782e5134753ac75aeb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zg0-9800000000-79154974b5c30f915ea5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-16648250719da0016f96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-7900000000-7ad97a16a3c93f065dc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pbi-9200000000-5a2fa29950e165d19eee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6e51c64fc7bc0e025373	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-7900000000-8d007c21807d42c8e41b	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum