Showing Metabocard for (2R,3S)-3-isopropylmalate (BASm0001920)
| Common Name | (2r,3s)-3-isopropylmalate |
|---|---|
| Description | 3-Isopropylmalic acid (CAS: 16048-89-8) is an intermediate in valine, leucine, and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867) and can be generated from the reduction of 2-isopropyl-3-oxosuccinate. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). This pathway is part of the super pathway of leucine, valine, and isoleucine biosynthesis that generates not only isoleucine and valine but also leucine. |
| Structure | |
| Molecular Formula | C7H12O5 |
| Average Mass | 176.16720 |
| Monoisotopic Mass | 176.06847 |
| IUPAC Name | (2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid |
| Traditional Name | (2r,3s)-2-hydroxy-3-isopropylbutanedioic acid |
| CAS Registry Number | 126576-14-5 |
| SMILES | CC(C)[C@H](C(=O)[O-])[C@@H](O)C(=O)[O-] |
| InChI Identifier | InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1 |
| InChI Key | RNQHMTFBUSSBJQ-CRCLSJGQSA-N |
| CHEBI ID | CHEBI:35121 |
| HMDB ID | HMDB0012156 |
| State | Solid |
| Water Solubility | 8.33e+01 g/l |
| logP | 0.28 |
| logS | -0.33 |
| pKa (Strongest Acidic) | 3.68 |
| pKa (Strongest Basic) | -4.02 |
| Hydrogen Acceptor Count | 5 |
| Hydrogen Donor Count | 3 |
| Polar Surface Area | 94.83 Ų |
| Rotatable Bond Count | 4 |
| Physiological Charge | -2 |
| Formal Charge | 0 |
| Refractivity | 38.60 m³·mol⁻¹ |
| Polarizability | 16.47 |