methyl (3S)-5-(2,6-difluorophenoxy)-3-[(2S)-2-[(2S)-5-methoxy-5-oxo-2-[(2S)-2-(quinolin-2-ylformamido)propanamido]pentanamido]-3-methylbutanamido]-4-oxopentanoate

• ChemBase ID: 106599
• Molecular Formular: C36H41F2N5O10
• Molecular Mass: 741.7350464
• Monoisotopic Mass: 741.28214898
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](C)NC(=O)c1ccc2ccccc2n1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)OC)C(=O)COc1c(F)cccc1F
• Canonical SMILES: COC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)COc1c(F)cccc1F)CC(=O)OC)C(C)C)NC(=O)[C@@H](NC(=O)c1ccc2c(n1)cccc2)C
• InChI: InChI=1S/C36H41F2N5O10/c1-19(2)31(36(50)42-27(17-30(46)52-5)28(44)18-53-32-22(37)10-8-11-23(32)38)43-35(49)26(15-16-29(45)51-4)41-33(47)20(3)39-34(48)25-14-13-21-9-6-7-12-24(21)40-25/h6-14,19-20,26-27,31H,15-18H2,1-5H3,(H,39,48)(H,41,47)(H,42,50)(H,43,49)/t20-,26-,27-,31-/m0/s1
• InChIKey: UIRLPKKPUHKVKW-DFMYRHPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-5-(2,6-difluorophenoxy)-3-[(2S)-2-[(2S)-5-methoxy-5-oxo-2-[(2S)-2-(quinolin-2-ylformamido)propanamido]pentanamido]-3-methylbutanamido]-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-5-(2,6-difluorophenoxy)-3-[(2S)-2-[(2S)-5-methoxy-5-oxo-2-[(2S)-2-(quinolin-2-ylformamido)propanamido]pentanamido]-3-methylbutanamido]-4-oxopentanoate
• Synonyms: Q-Ala-Glu(OMe)-Val-Asp(OMe)-OPH; Q-AE(OMe)VD(OMe)-OPH; Quinoline-Ala-Glu(OMe)-Val-Asp(OMe)-Difluorophenoxymethylketone

Database IDs

• PubChem SID: 162105543
• PubChem CID: 25108759

CALCULATED PROPERTIES

• Acid pKa: 11.0124035
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 2.3445058
• LogD (pH = 7.4): 2.3444173
• Log P: 2.3445115
• Molar Refractivity: 181.3587 cm^3
• Polarizability: 71.6744 Å^3
• Polar Surface Area: 208.19 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03OPH033

A potent, cell-permeable, and irreversible inhibitor of Group III caspases (caspase-6, caspase-8, caspase-9, and caspase-10), although more effective towards caspases-6 and -8. Also inhibits caspase-1 and caspase-3. When using with purified native or recombinant enzyme, pretreatment with an esterase is required.