(2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]-2-{[(9R,10R)-10-hydroxy-9,10-dihydrophenanthren-9-yl]sulfanyl}ethyl]carbamoyl}butanoic acid

• ChemBase ID: 1604
• Molecular Formular: C24H27N3O7S
• Molecular Mass: 501.55208
• Monoisotopic Mass: 501.15697122
• SMILES: N[C@@H](CCC(=O)N[C@H](CS[C@H]1[C@H](O)c2ccccc2c2ccccc12)C(=O)NCC(=O)O)C(=O)O
• Canonical SMILES: O=C(N[C@@H](C(=O)NCC(=O)O)CS[C@H]1[C@H](O)c2ccccc2c2c1cccc2)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C24H27N3O7S/c25-17(24(33)34)9-10-19(28)27-18(23(32)26-11-20(29)30)12-35-22-16-8-4-2-6-14(16)13-5-1-3-7-15(13)21(22)31/h1-8,17-18,21-22,31H,9-12,25H2,(H,26,32)(H,27,28)(H,29,30)(H,33,34)/t17-,18+,21+,22+/m0/s1
• InChIKey: JNNIZILNBMPOAC-XHIHJMKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]-2-{[(9R,10R)-10-hydroxy-9,10-dihydrophenanthren-9-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1S)-1-(carboxymethylcarbamoyl)-2-{[(9R,10R)-10-hydroxy-9,10-dihydrophenanthren-9-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
• Synonyms: (9r,10r)-9-(S-Glutathionyl)-10-Hydroxy-9,10-Dihydrophenanthrene; (9s,10s)-9-(S-Glutathionyl)-10-Hydroxy-9,10-Dihydrophenanthrene

Database IDs

• PubChem SID: 46506704; 46504778; 160965061
• PubChem CID: 46936232

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8015238
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -4.0401974
• LogD (pH = 7.4): -5.485661
• Log P: -2.2499523
• Molar Refractivity: 127.8774 cm^3
• Polarizability: 51.32983 Å^3
• Polar Surface Area: 179.05 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.31
• LOG S: -4.21
• Solubility (Water): 3.10e-02 g/l

DETAILS

DrugBank - DB04187

Drug information: experimental

DrugBank - DB01834

Drug information: experimental