(2R)-2-acetamido-3-[(2,3,4-trihydroxybutyl)sulfanyl]propanoic acid

• ChemBase ID: 179133
• Molecular Formular: C9H17NO6S
• Molecular Mass: 267.29938
• Monoisotopic Mass: 267.07765827
• SMILES: OCC(C(CSC[C@H](NC(=O)C)C(=O)O)O)O
• Canonical SMILES: OCC(C(CSC[C@@H](C(=O)O)NC(=O)C)O)O
• InChI: InChI=1S/C9H17NO6S/c1-5(12)10-6(9(15)16)3-17-4-8(14)7(13)2-11/h6-8,11,13-14H,2-4H2,1H3,(H,10,12)(H,15,16)/t6-,7?,8?/m0/s1
• InChIKey: QGRUOXFPDCTBCA-KKMMWDRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-[(2,3,4-trihydroxybutyl)sulfanyl]propanoic acid
• IUPAC Traditional name: (2R)-2-acetamido-3-[(2,3,4-trihydroxybutyl)sulfanyl]propanoic acid
• Synonyms: N-Acetyl-S-(2,3,4-trihydroxybutyl)-L-cysteine; S-(2,3,4-Trihydroxybutyl)mercapturic Acid (Mixture of Diatstereomers)

Database IDs

• CAS Number: 219965-90-9
• PubChem SID: 164235043
• PubChem CID: 46783183

CALCULATED PROPERTIES

• Rotatable Bonds: 8
• Lipinski's Rule of Five: true
• Acid pKa: 3.7033305
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.3303533
• LogD (pH = 7.4): -5.838891
• Log P: -2.534761
• Molar Refractivity: 60.7389 cm^3
• Polarizability: 24.194336 Å^3
• Polar Surface Area: 127.09 Å^2

PROPERTIES

Physical Property

• Apperance: Colorless Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T795040

A metabolite of butadiene and butadiene monoepoxide; relevance to cancer susceptibility.

REFERENCES

• Gray, J., et al.: Xenobiotica, 1, 55 (1971)
• Cheng, X., et al.: Drug Metab. Dispos., 21, 121 (1971)
• Bechtold, W., et al.: Toxicol Appl., Pharmacol., 127, 44 (1971)
• Acquavella, J., et al.: Toxicology, 113, 148 (1971)
• Nieusma, J., et al.: Chem. Res. Toxi