trisodium 2-hydroxy-1-methylpropane-1,2,3-tricarboxylate

• ChemBase ID: 153225
• Molecular Formular: C7H7Na3O7
• Molecular Mass: 272.09559
• Monoisotopic Mass: 271.98848541
• SMILES: CC(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])O.[Na+].[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)CC(C(C(=O)[O-])C)(C(=O)[O-])O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C7H10O7.3Na/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);;;/q;3*+1/p-3
• InChIKey: HPLKAWNRQOHUKD-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium 2-hydroxy-1-methylpropane-1,2,3-tricarboxylate
• IUPAC Traditional name: trisodium 2-methylcitrate
• Synonyms: Trisodium (2RS,3SR)-3-carboxy-3-hydroxy-2-methyl-pentanedioate; Trisodium (2RS,3RS)-2-methylcitrate

Database IDs

• MDL Number: MFCD16875437
• PubChem SID: 162247364
• PubChem CID: 71311617

CALCULATED PROPERTIES

• Acid pKa: 3.1832433
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -4.1271653
• LogD (pH = 7.4): -8.7069
• Log P: -0.7797012
• Molar Refractivity: 72.7097 cm^3
• Polarizability: 15.894152 Å^3
• Polar Surface Area: 140.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥85% (mixture of diastereomers, NMR)
• Impurities: ≤5% water
• Quality: mixture of diastereomers
• Empirical Formula (Hill Notation): C7H7Na3O7

DETAILS

Sigma Aldrich - 59464

Biochem/physiol Actions
MCA is a diagnostic marker metabolite which cumulates in body fluids of patients suffering from the following inherited metabolic diseases: propionic acidemia (PA), methylmalonic aciduris (MMA), holocarboxylase synthetase deficiency (HCSD)1,2. There MCA occurs as a mixture of (2S,3S)- and (2R,3S)-stereoisomers.