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

• ChemBase ID: 3360
• Molecular Formular: C19H26N4O10S
• Molecular Mass: 502.49554
• Monoisotopic Mass: 502.13696405
• SMILES: N[C@@H](CCC(=O)N[C@H](CS[C@H](CO)COc1ccc(cc1)[N+](=O)[O-])C(=O)NCC(=O)O)C(=O)O
• Canonical SMILES: OC[C@H](COc1ccc(cc1)[N+](=O)[O-])SC[C@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C19H26N4O10S/c20-14(19(29)30)5-6-16(25)22-15(18(28)21-7-17(26)27)10-34-13(8-24)9-33-12-3-1-11(2-4-12)23(31)32/h1-4,13-15,24H,5-10,20H2,(H,21,28)(H,22,25)(H,26,27)(H,29,30)/t13-,14+,15-/m1/s1
• InChIKey: YWXHXYSGHBAIBL-QLFBSQMISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-1-hydroxy-3-(4-nitrophenoxy)propan-2-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1S)-1-(carboxymethylcarbamoyl)-2-{[(2R)-1-hydroxy-3-(4-nitrophenoxy)propan-2-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
• Synonyms: 1-Hydroxy-2-S-Glutathionyl-3-Para-Nitrophenoxy-Propane

Database IDs

• PubChem SID: 160966801; 46505823
• PubChem CID: 46936761

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8042638
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -5.724403
• LogD (pH = 7.4): -7.1882067
• Log P: -3.9573965
• Molar Refractivity: 117.8359 cm^3
• Polarizability: 45.829205 Å^3
• Polar Surface Area: 234.1 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.89
• LOG S: -3.26
• Solubility (Water): 2.74e-01 g/l

DETAILS

DrugBank - DB03706

Drug information: experimental