(2S)-N-[(3S)-7-amino-1-chloro-2-oxoheptan-3-yl]-2-[(2R)-2-amino-3-methylbutanamido]-4-methylpentanamide

• ChemBase ID: 106478
• Molecular Formular: C18H35ClN4O3
• Molecular Mass: 390.9485
• Monoisotopic Mass: 390.23976868
• SMILES: CC(C)C[C@H](NC(=O)[C@H](N)C(C)C)C(=O)N[C@@H](CCCCN)C(=O)CCl
• Canonical SMILES: NCCCC[C@@H](C(=O)CCl)NC(=O)[C@@H](NC(=O)[C@@H](C(C)C)N)CC(C)C
• InChI: InChI=1S/C18H35ClN4O3/c1-11(2)9-14(23-18(26)16(21)12(3)4)17(25)22-13(15(24)10-19)7-5-6-8-20/h11-14,16H,5-10,20-21H2,1-4H3,(H,22,25)(H,23,26)/t13-,14-,16+/m0/s1
• InChIKey: BFFGVNDZOIYMKV-OFQRWUPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(3S)-7-amino-1-chloro-2-oxoheptan-3-yl]-2-[(2R)-2-amino-3-methylbutanamido]-4-methylpentanamide
• IUPAC Traditional name: (2S)-N-[(3S)-7-amino-1-chloro-2-oxoheptan-3-yl]-2-[(2R)-2-amino-3-methylbutanamido]-4-methylpentanamide
• Synonyms: D-Val-Leu-Lys-CMK; D-VLK-CMK; D-Val-Leu-Lys-Chloromethylketone

Database IDs

• PubChem SID: 162105475
• PubChem CID: 7408537

CALCULATED PROPERTIES

• Acid pKa: 12.154782
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.193984
• LogD (pH = 7.4): -1.9498757
• Log P: 1.2249247
• Molar Refractivity: 103.3778 cm^3
• Polarizability: 41.279213 Å^3
• Polar Surface Area: 127.31 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03CK024

A very efficient inhibitor for Human Thrombin. K2/K1 = 23,000 M^-1s^-1

REFERENCES

• Collen, D. et al., Biochem. Biophys. Acta., 165:158 (1980).