5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-[(1S)-1-{[(1S)-1-{[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]pentanamide

• ChemBase ID: 106476
• Molecular Formular: C26H36ClN5O5S
• Molecular Mass: 566.11254
• Monoisotopic Mass: 565.21256796
• SMILES: C[C@H](NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)CCl
• Canonical SMILES: ClCC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)C)C
• InChI: InChI=1S/C26H36ClN5O5S/c1-15(28-22(34)11-7-6-10-21-23-19(14-38-21)31-26(37)32-23)24(35)29-16(2)25(36)30-18(20(33)13-27)12-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-19,21,23H,6-7,10-14H2,1-2H3,(H,28,34)(H,29,35)(H,30,36)(H2,31,32,37)/t15-,16-,18-,19-,21-,23-/m0/s1
• InChIKey: NJDXMHWKYDNKQK-BTFREDBVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-[(1S)-1-{[(1S)-1-{[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]pentanamide
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-N-[(1S)-1-{[(1S)-1-{[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]pentanamide
• Synonyms: Biotin-Ala-Ala-Phe-CMK; Biotin-AAF-CMK; Biotin-Ala-Ala-Phe-Chloromethylketone

Database IDs

• PubChem SID: 162105474
• PubChem CID: 25108656

CALCULATED PROPERTIES

• Acid pKa: 11.709884
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 1.2331618
• LogD (pH = 7.4): 1.2331434
• Log P: 1.2331624
• Molar Refractivity: 144.8664 cm^3
• Polarizability: 56.742332 Å^3
• Polar Surface Area: 145.5 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03CK022C

An inhibitor for Chymotrypsin.

REFERENCES

• Glas, R. et al., Nature, 392:618 (1998).