benzyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride

• ChemBase ID: 69730
• Molecular Formular: C21H27ClN2O4
• Molecular Mass: 406.90308
• Monoisotopic Mass: 406.16593503
• SMILES: C(=O)([C@@H](N)CCCCNC(=O)OCc1ccccc1)OCc1ccccc1.Cl
• Canonical SMILES: O=C(OCc1ccccc1)NCCCC[C@@H](C(=O)OCc1ccccc1)N.Cl
• InChI: InChI=1S/C21H26N2O4.ClH/c22-19(20(24)26-15-17-9-3-1-4-10-17)13-7-8-14-23-21(25)27-16-18-11-5-2-6-12-18;/h1-6,9-12,19H,7-8,13-16,22H2,(H,23,25);1H/t19-;/m0./s1
• InChIKey: XHBTZNKKLKICJY-FYZYNONXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride
• IUPAC Traditional name: benzyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride
• Synonyms: N6-[(Phenylmethoxy)carbonyl]-L-lysine Phenylmethyl Ester Hydrochloride; N6-Carbobenzoxy-L-lysine Benzyl Ester Hydrochloride; NSC 88180; N6-Carbobenzyloxy-L-lysine Benzyl Ester Hydrochloride; Nε-Z-L-lysine benzyl ester hydrochloride; H-Lys(Z)-OBzl hydrochloride; N6-Cbz-L-Lysine benzyl ester hydrochloride; EPSILON-CARBOBENZOXY-L-LYSINE BENZYL ESTER HCl; Nε-Z-L-赖氨酸苄酯 盐酸盐; H-Lys(Z)-OBzl 盐酸盐

Database IDs

• CAS Number: 114331-06-5; 6366-70-7
• EC Number: 228-859-9
• MDL Number: MFCD00038981
• Beilstein Number: 3580519
• PubChem SID: 24890359; 162035455
• PubChem CID: 11750132

CALCULATED PROPERTIES

• Acid pKa: 15.509419
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4499179
• LogD (pH = 7.4): 3.0228999
• Log P: 3.322366
• Molar Refractivity: 102.8712 cm^3
• Polarizability: 40.679466 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 135-137°C
• Optical Rotation: [α]20/D -6.5±1°, c = 0.5% in 0.1 M HCl

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• RTECS: OL5685000
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC); 95+%
• Empirical Formula (Hill Notation): C21H26N2O4 · HCl

DETAILS

MP Biomedicals - 05207022

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - C176525

Useful for the preparation of pseudopeptides as thrombolytic agents.

REFERENCES

• Yabe, Y., et al.: J. Pharmacol. Exp. Ther., 289, 1176 (1999)
• Hines, I., et al.: Curr. Med. Chem., 10, 2661 (1999)