(2R)-2-amino-3-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}propanoic acid

• ChemBase ID: 178017
• Molecular Formular: C9H18N2O3S3
• Molecular Mass: 298.44582
• Monoisotopic Mass: 298.04795545
• SMILES: CS(=O)CCCCNC(=S)SC[C@H](N)C(=O)O
• Canonical SMILES: CS(=O)CCCCNC(=S)SC[C@@H](C(=O)O)N
• InChI: InChI=1S/C9H18N2O3S3/c1-17(14)5-3-2-4-11-9(15)16-6-7(10)8(12)13/h7H,2-6,10H2,1H3,(H,11,15)(H,12,13)/t7-,17?/m0/s1
• InChIKey: PUPMSTCTVNEOCX-ISJKBYAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}propanoic acid
• Synonyms: S-[[[4-(Methylsulfinyl)butyl]amino]thioxomethyl]-L-cysteine; D,L-Sulforaphane-L-cysteine

Database IDs

• CAS Number: 364083-21-6
• PubChem SID: 164233927
• PubChem CID: 10402443

CALCULATED PROPERTIES

• Acid pKa: 2.3903408
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.0197344
• LogD (pH = 7.4): -3.3013947
• Log P: -3.0168014
• Molar Refractivity: 77.4943 cm^3
• Polarizability: 30.653433 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Light Brown Waxy Solid
• Melting Point: 113-116°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S699410

A metabolite of Sulforaphane. 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