(2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]-2-{[(2R,3S,5R)-5-hydroxy-2-pentyloxolan-3-yl]sulfanyl}ethyl]carbamoyl}butanoic acid

• ChemBase ID: 4092
• Molecular Formular: C19H33N3O8S
• Molecular Mass: 463.54562
• Monoisotopic Mass: 463.19883603
• SMILES: CCCCC[C@H]1O[C@@H](O)C[C@@H]1SC[C@@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O
• Canonical SMILES: CCCCC[C@H]1O[C@H](C[C@@H]1SC[C@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)O
• InChI: InChI=1S/C19H33N3O8S/c1-2-3-4-5-13-14(8-17(26)30-13)31-10-12(18(27)21-9-16(24)25)22-15(23)7-6-11(20)19(28)29/h11-14,17,26H,2-10,20H2,1H3,(H,21,27)(H,22,23)(H,24,25)(H,28,29)/t11-,12+,13+,14-,17+/m0/s1
• InChIKey: ICRIFHIWWXQBPY-GMIGGYDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]-2-{[(2R,3S,5R)-5-hydroxy-2-pentyloxolan-3-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: @gshna
• Synonyms: GSHNA

Database IDs

• PubChem SID: 160967525; 46506521
• PubChem CID: 46936997

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8051393
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.574754
• LogD (pH = 7.4): -6.0187073
• Log P: -2.782771
• Molar Refractivity: 110.9135 cm^3
• Polarizability: 44.568485 Å^3
• Polar Surface Area: 188.28 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.81
• LOG S: -2.89
• Solubility (Water): 5.94e-01 g/l

DETAILS

DrugBank - DB04521

Drug information: experimental