tert-butyl N-[(1S)-1-{[(1S)-1-{[(2S)-1-(benzylsulfanyl)-4-(methylsulfanyl)-1-oxobutan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamate

• ChemBase ID: 106675
• Molecular Formular: C23H35N3O5S2
• Molecular Mass: 497.6711
• Monoisotopic Mass: 497.20181324
• SMILES: CSCC[C@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(=O)SCc1ccccc1
• Canonical SMILES: CSCC[C@@H](C(=O)SCc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)C)C
• InChI: InChI=1S/C23H35N3O5S2/c1-15(24-19(27)16(2)25-22(30)31-23(3,4)5)20(28)26-18(12-13-32-6)21(29)33-14-17-10-8-7-9-11-17/h7-11,15-16,18H,12-14H2,1-6H3,(H,24,27)(H,25,30)(H,26,28)/t15-,16-,18-/m0/s1
• InChIKey: DUFKYUBISAAVFH-BQFCYCMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1S)-1-{[(1S)-1-{[(2S)-1-(benzylsulfanyl)-4-(methylsulfanyl)-1-oxobutan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-{[(1S)-1-{[(2S)-1-(benzylsulfanyl)-4-(methylsulfanyl)-1-oxobutan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamate
• Synonyms: Boc-Ala-Ala-Met-Thiobenzyl Ester; Boc-AAM-Thiobenzyl Ester; Boc-Ala-Ala-Met-Thiobenzyl Ester

Database IDs

• PubChem SID: 162105613
• PubChem CID: 25108820

CALCULATED PROPERTIES

• Acid pKa: 12.035781
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.012995
• LogD (pH = 7.4): 3.0129862
• Log P: 3.0129952
• Molar Refractivity: 132.7804 cm^3
• Polarizability: 52.22482 Å^3
• Polar Surface Area: 113.6 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03SB029

A colorimetric substrate for Granzyme A.

REFERENCES

• Poe, M. et al., J. Biol. Chem., 226(1):98 (1991).
• Odake, S. et al., Biochem., 30:2217 (1991).
• Smyth, M.J. et al., J. Biol. Chem., 267(34):24418 (1992).