disodium (2S)-2-hydroxypentanedioate

• ChemBase ID: 154925
• Molecular Formular: C5H6Na2O5
• Molecular Mass: 192.07768
• Monoisotopic Mass: 192.00106185
• SMILES: C(CC(=O)[O-])[C@@H](C(=O)[O-])O.[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)CC[C@@H](C(=O)[O-])O.[Na+].[Na+]
• InChI: InChI=1S/C5H8O5.2Na/c6-3(5(9)10)1-2-4(7)8;;/h3,6H,1-2H2,(H,7,8)(H,9,10);;/q;2*+1/p-2/t3-;;/m0../s1
• InChIKey: DZHFTEDSQFPDPP-QTNFYWBSSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S)-2-hydroxypentanedioate
• IUPAC Traditional name: disodium L-2-hydroxyglutarate
• Synonyms: (S)-2-Hydroxypentanedioic acid disodium salt; Disodium (S)-2-hydroxyglutarate; L-α-Hydroxyglutaric acid disodium salt; (2S)-2-Hydroxypentanedioic Acid; L-2-Hydroxyglutaric Acid Disodium Salt; (S)-α-Hydroxyglutaric Acid Disodium Salt; L-2-Hydroxyglutarate Disodium Salt; (2S)-2-Hydroxyglutaric Acid Disodium Salt

Database IDs

• CAS Number: 63512-50-5
• Beilstein Number: 5318042
• PubChem SID: 162249063
• PubChem CID: 56845267

CALCULATED PROPERTIES

• Acid pKa: 3.276486
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -4.3875756
• LogD (pH = 7.4): -7.3476586
• Log P: -0.8249802
• Molar Refractivity: 51.3044 cm^3
• Polarizability: 11.659656 Å^3
• Polar Surface Area: 100.49 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >300°C
• Optical Rotation: [α]/D -8.5±1.5°, c = 1 in 0.1 M NaOH

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC)
• Impurities: ≤6.0% water
• Linear Formula: C5H6O5Na2

DETAILS

Sigma Aldrich - 90790

Biochem/physiol Actions
L-alpha-Hydroxyglutaric acid accumulates as a result of a rare defect in L-2-HG dehydogenase, leading to the metabolic disorder L-2-hydroxyglutaric aciduria (L-2HGA). L-2HGA is associated with neuronal defects, leukodystrophy and linked to an increased risk of brain tumors.

Toronto Research Chemicals - H942570

A potential inhibitor of glutamate carboxypeptidase.

REFERENCES

• Wolcott, T.G., et al.: Biochem. Biophys. Res. Commun., 57, 709 (1974)
• Knowles, P.F., et al.: Eur. J. Biochem., 114, 139 (1974)