Showing Metabocard for (2S,3S)-2-methylcitrate (BASm0003751)
| Common Name | (2s,3s)-2-methylcitrate |
|---|---|
| Description | Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000 , 232050 ), methylmalonic aciduria (MMA; OMIM 251000 , 251120 ) and multiple carboxylase deficiency (OMIM 253260 , 253270 ), which are inherited disorders. MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine (PMID: 17295121 ). |
| Structure | |
| Molecular Formula | C7H10O7 |
| Average Mass | 206.15010 |
| Monoisotopic Mass | 206.04265 |
| IUPAC Name | 2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid |
| Traditional Name | 2-methylcitric acid |
| CAS Registry Number | 6061-96-7 |
| SMILES | C[C@H](C(=O)[O-])[C@@](O)(CC(=O)[O-])C(=O)[O-] |
| InChI Identifier | InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13) |
| InChI Key | YNOXCRMFGMSKIJ-UHFFFAOYSA-N |
| CHEBI ID | CHEBI:58853 |
| HMDB ID | HMDB0000379 |
| State | Solid |
| Water Solubility | 1.75e+02 g/l |
| logP | -0.89 |
| logS | -0.07 |
| pKa (Strongest Acidic) | 3.18 |
| pKa (Strongest Basic) | -4.26 |
| Hydrogen Acceptor Count | 7 |
| Hydrogen Donor Count | 4 |
| Polar Surface Area | 132.13 Ų |
| Rotatable Bond Count | 5 |
| Physiological Charge | -3 |
| Formal Charge | 0 |
| Refractivity | 40.20 m³·mol⁻¹ |
| Polarizability | 17.21 |