(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(1H-indol-3-ylmethyl)sulfanyl]ethyl]carbamoyl}butanoic acid

• ChemBase ID: 169720
• Molecular Formular: C19H24N4O6S
• Molecular Mass: 436.48206
• Monoisotopic Mass: 436.14165551
• SMILES: C(SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@H](N)C(=O)O)c1c2ccccc2[nH]c1
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSCc1c[nH]c2c1cccc2)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C19H24N4O6S/c20-13(19(28)29)5-6-16(24)23-15(18(27)22-8-17(25)26)10-30-9-11-7-21-14-4-2-1-3-12(11)14/h1-4,7,13,15,21H,5-6,8-10,20H2,(H,22,27)(H,23,24)(H,25,26)(H,28,29)/t13-,15-/m0/s1
• InChIKey: LLXMBNSNAAVMLO-ZFWWWQNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(1H-indol-3-ylmethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-[(1H-indol-3-ylmethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
• Synonyms: L-γ-Glutamyl-S-(1H-indol-3-ylmethyl)-L-cysteinylglycine; N-[N-L-γ-Glutamyl-S-(1H-indol-3-ylmethyl)-L-cysteinyl]glycine; 3-Glutathionyl-S-methylindole

Database IDs

• CAS Number: 101038-93-1
• PubChem SID: 162263852
• PubChem CID: 71317122

CALCULATED PROPERTIES

• Acid pKa: 1.8092943
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -4.3642554
• LogD (pH = 7.4): -5.939242
• Log P: -2.761177
• Molar Refractivity: 109.5142 cm^3
• Polarizability: 43.883595 Å^3
• Polar Surface Area: 174.61 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol (Sparingly); Water (Sparingly)
• Apperance: Pale Yellow Solid
• Melting Point: 192-194°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G597985

A metabolite of 3-Methylindole bioactivated by CYP2A13.

REFERENCES

• Harrison, A., et al.: Biochem. Pharmacol., 43, 1421 (1992)
• Lai, W., et al.: J. Pharmacol. Exp. Ther., 291, 292 (1992)
• Yan, Z., et al.: Drug Metab. Dispos., 33, 1867 (1992)