ECMDB: 2-Isopropylmalic acid (ECMDB00402) (M2MDB000135)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (1515)

Record Information

Version

2.0

Creation Date

2012-05-31 10:26:35 -0600

Update Date

2015-09-13 12:56:08 -0600

Secondary Accession Numbers

ECMDB00402

Identification

Name:

2-Isopropylmalic acid

Description

2-Isopropylmalic acid is involved in valine, leucine and isoleucine biosynthesis and pyruvate metabolism pathways. In pyruvate metabolism, 2-isopropylmalate synthase (EC:2.3.3.13) catalyzes the formation of 2-Isopropylmalic acid from acetyl-CoA. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2S)-2-Isopropylmalate
(2S)-2-Isopropylmalic acid
2-D-Threo-hydroxy-3-carboxy-isocaproate
2-D-Threo-hydroxy-3-carboxy-isocaproic acid
2-Hydroxy-2-isopropylsuccinate
2-Hydroxy-2-isopropylsuccinic acid
2-Isopropyl-2-hydroxybutanedioate
2-Isopropyl-2-hydroxybutanedioic acid
2-Isopropyl-Malate
2-Isopropyl-Malic acid
2-Isopropylmalate
2-Isopropylmalic acid
3-Carboxy-2-hydroxy-4-methylpentanoate
3-Carboxy-2-hydroxy-4-methylpentanoic acid
3-Carboxy-3-hydroxyisocaproate
3-Carboxy-3-hydroxyisocaproic acid
3-Isopropylmalate
3-Isopropylmalic acid
A-Isopropylmalate
A-Isopropylmalic acid
Alpha-Isopropylmalate
Alpha-Isopropylmalic acid
b-Isopropylmalate
b-Isopropylmalic acid
Beta-Isopropylmalate
Beta-Isopropylmalic acid
α-Isopropylmalate
α-Isopropylmalic acid
β-Isopropylmalate
β-Isopropylmalic acid

Chemical Formula:

C₇H₁₂O₅

Weight:

Average: 176.1672
Monoisotopic: 176.068473494

InChI Key:

BITYXLXUCSKTJS-ZETCQYMHSA-N

InChI:

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

CAS number:

3237-44-3

IUPAC Name:

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

Traditional IUPAC Name:

2-isopropyl-malic acid

SMILES:

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

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 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

144-146 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	181 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Leucine Biosynthesis	PW000811
Secondary Metabolite: Leucine biosynthesis	PW000980
Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvate	PW000978

KEGG Pathways:

Metabolic pathways eco01100
Pyruvate metabolism ec00620
Valine, leucine and isoleucine biosynthesis ec00290

EcoCyc Pathways:

isoleucine biosynthesis I (from threonine) LEUSYN-PWY

Concentrations

Not Available

Spectra

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	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Pinkston D, Spiteller G, Von Henning H, Matthaei D: High resolution gas chromatography mass spectrometry of the methyl esters of organic acids from uremic hemofiltrates. J Chromatogr. 1981 Apr 10;223(1):1-19. Pubmed: 7251751
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Verhaeghe BJ, Van Bocxlaer JF, De Leenheer AP: Gas chromatographic/mass spectrometric identification of 3-hydroxydicarboxylic acids in urine. Biol Mass Spectrom. 1992 Jan;21(1):27-32. Pubmed: 1591279
Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	28635
HMDB ID	HMDB00402
Pubchem Compound ID	5280523
Kegg ID	C02504
ChemSpider ID	4444155
Wikipedia ID	Isopropylmalic acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. 2-isopropylmalate synthase

General function:: Involved in 2-isopropylmalate synthase activity
Specific function:: Catalyzes the condensation of the acetyl group of acetyl-CoA with 3-methyl-2-oxobutanoate (2-oxoisovalerate) to form 3-carboxy-3-hydroxy-4-methylpentanoate (2-isopropylmalate)
Gene Name:: leuA
Uniprot ID:: P09151
Molecular weight:: 57297

Reactions

Acetyl-CoA + 3-methyl-2-oxobutanoate + H(2)O = (2S)-2-isopropylmalate + CoA.

Protein Details

2. 3-isopropylmalate dehydratase large subunit

General function:: Involved in 3-isopropylmalate dehydratase activity
Specific function:: Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:: leuC
Uniprot ID:: P0A6A6
Molecular weight:: 49882

Reactions

(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.

Protein Details

3. 3-isopropylmalate dehydratase small subunit

General function:: Involved in 3-isopropylmalate dehydratase activity
Specific function:: Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:: leuD
Uniprot ID:: P30126
Molecular weight:: 22487

Reactions

(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.

2-Isopropylmalic acid (ECMDB00402) (M2MDB000135)

Structure for #<Compound:0xa2905fcc>

Enzymes

Reactions

Reactions

Reactions