(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}ethyl]carbamoyl}butanoic acid

• ChemBase ID: 178018
• Molecular Formular: C16H28N4O7S3
• Molecular Mass: 484.61112
• Monoisotopic Mass: 484.11201226
• SMILES: CS(=O)CCCCNC(=S)SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSC(=S)NCCCCS(=O)C)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C16H28N4O7S3/c1-30(27)7-3-2-6-18-16(28)29-9-11(14(24)19-8-13(22)23)20-12(21)5-4-10(17)15(25)26/h10-11H,2-9,17H2,1H3,(H,18,28)(H,19,24)(H,20,21)(H,22,23)(H,25,26)/t10-,11-,30?/m0/s1
• InChIKey: ROARKYNVUQLTDP-QGQIPBJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-{[(4-methanesulfinylbutyl)carbamothioyl]sulfanyl}ethyl]carbamoyl}butanoic acid
• Synonyms: L-γ-Glutamyl-S-[[[4-(methylsulfinyl)butyl]amino]thioxomethyl]-L-cysteinylglycine; SFN-GSH; D,L-Sulforaphane Glutathione

Database IDs

• CAS Number: 289711-21-3
• PubChem SID: 164233928
• PubChem CID: 45040448

CALCULATED PROPERTIES

• Acid pKa: 1.7937225
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -6.8077235
• LogD (pH = 7.4): -8.543613
• Log P: -5.111216
• Molar Refractivity: 118.3856 cm^3
• Polarizability: 46.63985 Å^3
• Polar Surface Area: 187.92 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 157-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S699430

The major metabolite of Sulforaphane. The Glutathione adduct of Sulforaphane.

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