ECMDB: Isopropylmaleate (ECMDB12241) (M2MDB000832)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (918)

Record Information

Version

2.0

Creation Date

2012-05-31 14:21:15 -0600

Update Date

2015-06-03 17:19:03 -0600

Secondary Accession Numbers

ECMDB12241

Identification

Name:

Isopropylmaleate

Description

Isopropylmaleate is an intermediate in branched chain amino acid metabolism (specifically L-leucine biosynthesis). It is a substrate for 3-isopropylmalate dehydratase. This enzyme catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

β-isopropylmaleate
β-isopropylmaleic acid
2-Isopropylmaleate
2-Isopropylmaleic acid
B-isopropylmaleate
b-Isopropylmaleic acid
Beta-Isopropylmaleate
Beta-Isopropylmaleic acid
Isopropylmaleic acid
β-Isopropylmaleate
β-Isopropylmaleic acid

Chemical Formula:

C₇H₁₀O₄

Weight:

Average: 158.1519
Monoisotopic: 158.057908808

InChI Key:

NJMGRJLQRLFQQX-HYXAFXHYSA-N

InChI:

InChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-

CAS number:

Not Available

IUPAC Name:

(2Z)-2-(propan-2-yl)but-2-enedioic acid

Traditional IUPAC Name:

2-isopropylmaleic acid

SMILES:

CC(C)C(=C\C(O)=O)\C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:17275 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	3.64 g/L	ALOGPS
logP	1.05	ALOGPS
logP	1.09	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.11 m³·mol⁻¹	ChemAxon
Polarizability	15.11 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
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	splash10-01ox-9800000000-c1dc75af0432077c0384	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-9470000000-5b930a576d9e4924347a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-45d74194c5fbfea04a10	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-7900000000-7e85e22040474be6339c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-9100000000-672bc73595a1f6b84201	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-1900000000-48b9e2f85f15343470ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-090a-5900000000-5c4991c8530e2f8a6eda	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-9400000000-0d37fa6e2313dc5f09a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ow-6900000000-9e65c798b41317f5b6e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9200000000-6dfbad4c912b766f9b7e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-74dbf533069b6e671b6c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-9800000000-698f88590edad48bf4c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-9400000000-d1228db2dbcd7906ae8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9000000000-a5bd12b0d9ab424964cc	View in MoNA
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
1D NMR	1H 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
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17275
HMDB ID	HMDB12241
Pubchem Compound ID	230410
Kegg ID	C02631
ChemSpider ID	4444164
Wikipedia ID	Isopropylmalic_acid
BioCyc ID	CPD-9451
EcoCyc ID	CPD-9451

Enzymes

Protein Details

1. 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

2. 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.

Isopropylmaleate (ECMDB12241) (M2MDB000832)

Structure for #<Compound:0xa8aba3bc>

Enzymes

Reactions

Reactions