4-hydroxy(1,2,3,4-13C4)butanoic acid sodium

• ChemBase ID: 170311
• Molecular Formular: C4H8NaO3
• Molecular Mass: 131.06490935
• Monoisotopic Mass: 131.05053275
• SMILES: O[13C](=O)[13CH2][13CH2][13CH2]O.[Na]
• Canonical SMILES: O[13CH2][13CH2][13CH2][13C](=O)O.[Na]
• InChI: InChI=1S/C4H8O3.Na/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/i1+1,2+1,3+1,4+1
• InChIKey: WFBCFGRDCIMEAM-UJNKEPEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy(1,2,3,4-^1^3C₄)butanoic acid sodium
• IUPAC Traditional name: 4-hydroxy(1,2,3,4-^1^3C₄)butanoic acid sodium
• Synonyms: γ-Hydroxybutyric Acid-13C4 Sodium Salt; 4-Hydroxybutanoic Acid-13C4 Sodium Salt; Anetamin-13C4 Sodium Salt; GHB-13C4; Xyrem-13C4; Oxybate-13C4 Sodium; NSC 84223-13C4; 4-Hydroxybutyric Acid-13C4 Sodium Salt

Database IDs

• PubChem SID: 164226221
• PubChem CID: 71748913

CALCULATED PROPERTIES

• Acid pKa: 4.440874
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.608916
• LogD (pH = 7.4): -3.371081
• Log P: -0.5149198
• Molar Refractivity: 23.8003 cm^3
• Polarizability: 9.344846 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H833017

An agonist to both GHB and GABAB neural receptors, exhibiting neurotransmitter-like effects. It has been used as a general anesthetic in treatment for sleep disorders and clinical depression, but also has been identified as a “date rape drug”.

REFERENCES

• Mamelak, M., et al.: Prog. Neurobiol., 89, 193 (2009)
• Zhang, L., et al.: App. Microbiol. Biotechnol., 84, 909 (2009)
• Pedraza, C., Int. J. Neuropsychopharmacol., 12, 1165 (2009)
• McGonigle, I., et al.: Biochem., 49, 2897 (2009)