P. aeruginosa Metabolome Database: Isopropylmaleate (PAMDB000832)

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

PAMDB000832

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 View Structure

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

Average Molecular Weight:

158.1519

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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
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 mg/mL	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:

3-Isopropylmalate <> Isopropylmaleate + Water
Isopropylmaleate + Water <> 2-Isopropylmalic acid
3-Carboxy-3-hydroxy-isocaproate <> Isopropylmaleate + Water
3-Isopropylmalate + Isopropylmaleate + Water <> 2-Isopropylmalic acid

Pathways:

Metabolic pathways pae01100
Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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

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	Not Available
BioCyc ID	CPD-9451
EcoCyc ID	CPD-9451

Isopropylmaleate (PAMDB000832)

Structure for Isopropylmaleate (PAMDB000832)