(2S)-2-{[(benzyloxy)carbonyl]amino}-2-cyclohexylacetic acid

• ChemBase ID: 163863
• Molecular Formular: C16H21NO4
• Molecular Mass: 291.34224
• Monoisotopic Mass: 291.14705816
• SMILES: C1CCCC(C1)[C@H](NC(=O)OCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)C1CCCCC1)OCc1ccccc1
• InChI: InChI=1S/C16H21NO4/c18-15(19)14(13-9-5-2-6-10-13)17-16(20)21-11-12-7-3-1-4-8-12/h1,3-4,7-8,13-14H,2,5-6,9-11H2,(H,17,20)(H,18,19)/t14-/m0/s1
• InChIKey: CUSYTUPJAYLNFQ-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}-2-cyclohexylacetic acid
• IUPAC Traditional name: (S)-{[(benzyloxy)carbonyl]amino}(cyclohexyl)acetic acid
• Synonyms: (αS)-α-[[(Phenylmethoxy)carbonyl]amino]cyclohexaneacetic Acid; (S)-α-[[(phenylmethoxy)carbonyl]amino]cyclohexaneacetic Acid; Cbz-Cyclohexyl-L-glycine

Database IDs

• CAS Number: 69901-75-3
• PubChem SID: 162257998
• PubChem CID: 16218812

CALCULATED PROPERTIES

• Acid pKa: 3.9592464
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.792729
• LogD (pH = 7.4): 0.15939811
• Log P: 3.3413749
• Molar Refractivity: 77.1737 cm^3
• Polarizability: 30.445433 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 111-114°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C227500

A gylicine derivative used in the preparation of peptides as inhibitors of serine proteases, particularly hepatitis C virus NS3-NS4A protease.

REFERENCES

• Perni, R.B. et al.: Bioorg. Med. Chem. Lett., 17, 3406 (2007)