Showing Metabocard for 2-isopropylmaleate (BASm0003186)
| Common Name | 2-isopropylmaleate |
|---|---|
| Description | 2-Isopropylmaleic acid 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 one or more methyl groups. However, branches other than methyl groups may be present. 2-Isopropylmaleic acid is a moderately acidic compound (based on its pKa). Isopropylmaleic acid is found in the leucine biosynthesis pathway. It is synthesized from oxoisovalerate by 2-isopropylmalate synthase and converted into isopropyl-3-oxosuccinate by 3-isopropylmalate dehydrogenase. The 2- and 3-isopropyl derivatives of isopropylmaleic acid are interconverted by the enzyme isopropylmalate dehydratase. |
| Structure | |
| Molecular Formula | C7H10O4 |
| Average Mass | 158.15190 |
| Monoisotopic Mass | 158.05791 |
| IUPAC Name | (2Z)-2-(propan-2-yl)but-2-enedioic acid |
| Traditional Name | 2-isopropylmaleic acid |
| CAS Registry Number | 44976-69-4 |
| SMILES | CC(C)/C(=C/C(=O)[O-])C(=O)[O-] |
| InChI Identifier | 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- |
| InChI Key | NJMGRJLQRLFQQX-HYXAFXHYSA-N |
| CHEBI ID | CHEBI:58085 |
| HMDB ID | HMDB0012241 |
| State | Solid |
| Water Solubility | 3.64e+00 g/l |
| logP | 1.05 |
| logS | -1.64 |
| pKa (Strongest Acidic) | 2.79 |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 74.6 Ų |
| Rotatable Bond Count | 3 |
| Physiological Charge | -2 |
| Formal Charge | 0 |
| Refractivity | 38.11 m³·mol⁻¹ |
| Polarizability | 15.11 |