trisodium (2R)-2-hydroxybutane-1,2,4-tricarboxylate

• ChemBase ID: 154861
• Molecular Formular: C7H7Na3O7
• Molecular Mass: 272.09559
• Monoisotopic Mass: 271.98848541
• SMILES: C(C[C@@](CC(=O)[O-])(C(=O)[O-])O)C(=O)[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)CC[C@](C(=O)[O-])(CC(=O)[O-])O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C7H10O7.3Na/c8-4(9)1-2-7(14,6(12)13)3-5(10)11;;;/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13);;;/q;3*+1/p-3/t7-;;;/m1.../s1
• InChIKey: SNTBDRNHMPWDFS-LSBIWMFESA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (2R)-2-hydroxybutane-1,2,4-tricarboxylate
• IUPAC Traditional name: trisodium (2R)-homocitrate
• Synonyms: (R)-Homocitrate trisodium salt; (R)-2-Hydroxy-1,2,4-butanetricarboxylic acid trisodium salt; Sodium (R)-homocitrate tribasic

Database IDs

• CAS Number: 320573-06-6
• MDL Number: MFCD16817602
• PubChem SID: 162248999
• PubChem CID: 44245540

CALCULATED PROPERTIES

• Acid pKa: 3.086704
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -5.4406986
• LogD (pH = 7.4): -9.87728
• Log P: -1.0340263
• Molar Refractivity: 72.8902 cm^3
• Polarizability: 15.894152 Å^3
• Polar Surface Area: 140.62 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -11.0±2.0°, c = 0.1 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Purity: ≥90.0% (qNMR)
• Impurities: ≤15.0% water
• Empirical Formula (Hill Notation): C7H7Na3O7

DETAILS

Sigma Aldrich - 67376

Biochem/physiol Actions
Important metabolite of lysine biosynthesis, pyruvate and 2-oxocarboxylic acid metabolism, homocitrate is as a sensor of lysine-pathway distress1, it has a dynamic role during nitrogen fixation2.