(2S)-N-{[(3-chloro-2-oxopropyl)carbamoyl]methyl}-2-acetamido-3-(4-hydroxyphenyl)propanamide

• ChemBase ID: 106469
• Molecular Formular: C16H20ClN3O5
• Molecular Mass: 369.8001
• Monoisotopic Mass: 369.10914844
• SMILES: CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCC(=O)NCC(=O)CCl
• Canonical SMILES: ClCC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C
• InChI: InChI=1S/C16H20ClN3O5/c1-10(21)20-14(6-11-2-4-12(22)5-3-11)16(25)19-9-15(24)18-8-13(23)7-17/h2-5,14,22H,6-9H2,1H3,(H,18,24)(H,19,25)(H,20,21)/t14-/m0/s1
• InChIKey: UNJCOQRVVTTYRW-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-{[(3-chloro-2-oxopropyl)carbamoyl]methyl}-2-acetamido-3-(4-hydroxyphenyl)propanamide
• IUPAC Traditional name: (2S)-N-{[(3-chloro-2-oxopropyl)carbamoyl]methyl}-2-acetamido-3-(4-hydroxyphenyl)propanamide
• Synonyms: Ac-Tyr-Gly-Gly-CMK; Ac-YGG-CMK; Ac-Tyr-Gly-Gly-Chloromethylketone

Database IDs

• PubChem SID: 162105964
• PubChem CID: 25108653

CALCULATED PROPERTIES

• Acid pKa: 9.500631
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.7507439
• LogD (pH = 7.4): -0.75410926
• Log P: -0.75070083
• Molar Refractivity: 90.4523 cm^3
• Polarizability: 35.031635 Å^3
• Polar Surface Area: 124.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true