Bovine Metabolome Database: Showing metabocard for 2-Isopropylmalic acid (BMDB0000402)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:30:05 UTC

Update Date

2020-04-22 15:03:24 UTC

BMDB ID

BMDB0000402

Secondary Accession Numbers

BMDB00402

Metabolite Identification

Common Name

2-Isopropylmalic acid

Description

2-Isopropylmalic acid, also known as (2S)-2-isopropylmalate, 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 2-Isopropylmalic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Hydroxy-2-isopropylsuccinic acid	ChEBI
(2S)-2-Isopropylmalate	ChEBI
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acid	ChEBI
(3S)-3-Carboxy-3-hydroxyisocaproic acid	ChEBI
(S)-2-Hydroxy-2-(isopropyl)succinic acid	ChEBI
3-Carboxy-3-hydroxy-4-methylpentanoate	ChEBI
3-Carboxy-3-hydroxyisocaproate	ChEBI
(2S)-2-Hydroxy-2-isopropylsuccinate	Generator
(2S)-2-Isopropylmalic acid	Generator
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoate	Generator
(3S)-3-Carboxy-3-hydroxyisocaproate	Generator
(S)-2-Hydroxy-2-(isopropyl)succinate	Generator
3-Carboxy-3-hydroxy-4-methylpentanoic acid	Generator
3-Carboxy-3-hydroxyisocaproic acid	Generator
2-Isopropylmalate	Generator
2-Hydroxy-2-isopropylsuccinate	HMDB
2-Hydroxy-2-isopropylsuccinic acid	HMDB
2-Isopropyl-2-hydroxybutanedioate	HMDB
2-Isopropyl-2-hydroxybutanedioic acid	HMDB
2-Isopropyl-malic acid	HMDB
a-Isopropylmalate	HMDB
a-Isopropylmalic acid	HMDB
alpha-Isopropylmalate	HMDB
alpha-Isopropylmalic acid	HMDB
(2S)-2-Hydroxy-2-(1-methylethyl)butanedioic acid	HMDB
(2S)-2-Hydroxy-2-(propan-2-yl)butanedioic acid	HMDB
(S)-(+)-2-Isopropylmalic acid	HMDB
2-Hydroxy-2-(1-methylethyl)butanedioic acid	HMDB
Α-isopropylmalate	HMDB
Α-isopropylmalic acid	HMDB
2-Isopropylmalic acid	HMDB

Chemical Formula

C₇H₁₂O₅

Average Molecular Weight

176.1672

Monoisotopic Molecular Weight

176.068473494

IUPAC Name

(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid

Traditional Name

2-isopropyl-malic acid

CAS Registry Number

3237-44-3

SMILES

CC(C)[C@@](O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1

InChI Key

BITYXLXUCSKTJS-ZETCQYMHSA-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

2-isopropylmalic acid (CHEBI:35128 )
Dicarboxylic acids (LMFA01170083 )

Ontology

Status

Expected 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	144 - 146 °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	-0.29	ALOGPS
logP	0.21	ChemAxon
logS	0.01	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-4.1	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	4	ChemAxon
Refractivity	38.58 m³·mol⁻¹	ChemAxon
Polarizability	16.37 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	splash10-0006-9400000000-1c869c73651e7e4e5dda	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00bl-9134000000-30fabfd0c26c38444fff	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)	splash10-004i-0900000000-1bb48f5ddadbf88b8f6c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00kr-9400000000-5df8f3f29d2e8a962cac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-05n0-9200000000-c62b1543d0e6a41388f1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014r-6900000000-983e4a8edd0725d26979	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-016r-1900000000-5aa4d41c6ff31081d9d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9200000000-d4b84f7b5f2a53ac5800	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-c680094e514a83eea978	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052o-9000000000-365c84abb7ec259fb43e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e28ea8cd657f96ff8357	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0690-1900000000-3b83300261e0daab2ef1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9700000000-2652db028b01706ac042	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9300000000-808bda4307e96bcfcc83	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-2900000000-9fa33cd594a81b5d67cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-055r-9700000000-8ab90438d0e6c9b7d0be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9100000000-41e1c40b755f8bfaf000	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01x9-9800000000-53afadde706df1ef69ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4bfe3581b4b94540fea0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1470f6a6a1859e452712	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-9a718ee22b675ce18980	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-8900000000-188b5287c7dbbce2559f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9000000000-2a93d25f081bcaa86a53	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000402

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

3-CARBOXY-3-HYDROXY-ISOCAPROATE

BiGG ID

Not Available

Wikipedia Link

Isopropylmalic acid

METLIN ID

339

PubChem Compound

5280523

PDB ID

Not Available

ChEBI ID

35128

References

Synthesis Reference

Schloss J V; Magolda R; Emptage M Synthesis of alpha-isopropylmalate, beta-isopropylmalate, and dimethylcitraconate. Methods in enzymology (1988), 166 92-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2-Isopropylmalic acid (BMDB0000402)

Structure for BMDB0000402 (2-Isopropylmalic acid)