Bovine Metabolome Database: Showing metabocard for Citramalic acid (BMDB0000426)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:30:33 UTC

Update Date

2020-05-05 18:39:45 UTC

BMDB ID

BMDB0000426

Secondary Accession Numbers

BMDB00426

Metabolite Identification

Common Name

Citramalic acid

Description

Citramalic acid, also known as citramalate or 2-methylmalate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review a significant number of articles have been published on Citramalic acid.

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 )

Ontology

Status

Detected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	107 - 111 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9200000000-d88cf81bb63b8badd74d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00gs-8492000000-d1c8fb9235f1de536d15	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000j-7900000000-efbe2adf2c82decc64a6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-052u-9000000000-3754186783f820cbff7c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052o-9000000000-0656e8e194378442727f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-2900000000-be1cc6b0ea685f5d7ac2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-002r-8900000000-7dd192ed79cd2d306ea5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9500000000-c96a62314140c10f1245	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-0002-2900000000-716fb416386753113137	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-20ae5f1dfa6847e56e0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-4bc688d98054e464cf07	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4r-9000000000-61294657ce4e2d5d6d05	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9400000000-d027e4da9369388ea3c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e7930822f64c0c43d7c0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9500000000-2e922f07663d3c399240	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9400000000-b372db83cd99e22fb0ac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-093483f4bf2d387fa405	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001a-5900000000-437d36fe16a8d6f79c68	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9200000000-6aed3a8e654948bbd5e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-31c6a41b79f5b68fa431	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uds-4900000000-0d782e5134753ac75aeb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zg0-9800000000-79154974b5c30f915ea5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-16648250719da0016f96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-7900000000-7ad97a16a3c93f065dc0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pbi-9200000000-5a2fa29950e165d19eee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6e51c64fc7bc0e025373	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-7900000000-8d007c21807d42c8e41b	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm

Biospecimen Locations

Mammary Gland

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details