2-acetamido-3-({[4-methanesulfinyl(2H8)butyl]carbamothioyl}sulfanyl)propanoic acid

• ChemBase ID: 177997
• Molecular Formular: C11H20N2O4S3
• Molecular Mass: 340.4825
• Monoisotopic Mass: 340.05852013
• SMILES: CS(=O)CCCCNC(=S)SCC(NC(=O)C)C(=O)O
• Canonical SMILES: CS(=O)CCCCNC(=S)SCC(C(=O)O)NC(=O)C
• InChI: InChI=1S/C11H20N2O4S3/c1-8(14)13-9(10(15)16)7-19-11(18)12-5-3-4-6-20(2)17/h9H,3-7H2,1-2H3,(H,12,18)(H,13,14)(H,15,16)
• InChIKey: IIHBKTCHILXGOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-({[4-methanesulfinyl(^2H₈)butyl]carbamothioyl}sulfanyl)propanoic acid
• IUPAC Traditional name: 2-acetamido-3-({[4-methanesulfinyl(^2H₈)butyl]carbamothioyl}sulfanyl)propanoic acid
• Synonyms: N-Acetyl-S-[[[4-(methylsulfinyl)butyl-d8]amino]thioxomethyl]-L-cysteine; Sulforaphane NAC; D,L-Sulforaphane-d8 N-Acetyl-L-cysteine

Database IDs

• CAS Number: 1354064-85-9
• PubChem SID: 164233907
• PubChem CID: 46782962

CALCULATED PROPERTIES

• Acid pKa: 3.9664636
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.4859884
• LogD (pH = 7.4): -4.3344913
• Log P: -0.940584
• Molar Refractivity: 86.9381 cm^3
• Polarizability: 34.055946 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699122

The major labelled metabolite of Sulforaphane. Sulforaphane (SFN) is an isothiocyanate from broccoli that induces phase 2 detoxification enzymes. Antitumor agent.

REFERENCES

• Singhal, D., et al.: J. Pharm. Sci., 87, 569 (1998)
• Cohen, J., et al.: J. Natl. Cancer. Inst., 92, 61 (1998)
• Johnson, B., et al.: J. Pharmacol. Exp. Ther., 305, 151 ( 2003), Petri, N., et al.: Drug Metabol. Dispos., 31, 805 (1998)
• Hu, R., et al.: J. Ph