(2R,3R)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid

• ChemBase ID: 130903
• Molecular Formular: C18H19NO5
• Molecular Mass: 329.34716
• Monoisotopic Mass: 329.12632271
• SMILES: c1ccc(cc1)C[C@H]([C@H](C(=O)O)O)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@@H]([C@H](C(=O)O)O)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C18H19NO5/c20-16(17(21)22)15(11-13-7-3-1-4-8-13)19-18(23)24-12-14-9-5-2-6-10-14/h1-10,15-16,20H,11-12H2,(H,19,23)(H,21,22)/t15-,16-/m1/s1
• InChIKey: JXJYTERRLRAUSF-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid
• IUPAC Traditional name: (2R,3R)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid
• Synonyms: N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid; (2R,3R)-3-(Z-amino)-2-hydroxy-4-phenylbutyric acid

Database IDs

• CAS Number: 62023-58-9
• MDL Number: MFCD00057840
• PubChem SID: 162225181; 24892655
• PubChem CID: 11131299

CALCULATED PROPERTIES

• Polarizability: 34.022728 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true
• Acid pKa: 3.7479486
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.8574109
• LogD (pH = 7.4): -0.67562485
• Log P: 2.609891
• Molar Refractivity: 86.7588 cm^3

PROPERTIES

Safety Information

• German water hazard class: 3

DETAILS

Sigma Aldrich - C3910

Preparation Note
CBZ-protected novel amino acid in epibestatin.