P. aeruginosa Metabolome Database: 2-Isopropylmalic acid (PAMDB000135)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000135

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 View Structure

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

Average Molecular Weight:

176.1672

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Hydroxy fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Branched fatty acid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	181.0 mg/mL	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:

Isopropylmaleate + Water <> 2-Isopropylmalic acid
alpha-Ketoisovaleric acid + Acetyl-CoA + Water + a-Ketoisovaleric acid <> 2-Isopropylmalic acid + Coenzyme A + Hydrogen ion
2-Isopropylmalic acid + Coenzyme A <> Acetyl-CoA + alpha-Ketoisovaleric acid + Water
3-Isopropylmalate + Isopropylmaleate + Water <> 2-Isopropylmalic acid
3-Methyl-2-oxovaleric acid + Water + Acetyl-CoA + 3-Methyl-2-oxovaleric acid > Coenzyme A + Hydrogen ion + 2-Isopropylmalic acid

Pathways:

Metabolic pathways pae01100
Pyruvate metabolism pae00620
Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

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)

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Links

External Links:

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

2-Isopropylmalic acid (PAMDB000135)

Structure for 2-Isopropylmalic acid (PAMDB000135)