(2R)-2-{[(benzyloxy)carbonyl]amino}-3-(phenylsulfanyl)propanoic acid

• ChemBase ID: 145253
• Molecular Formular: C17H17NO4S
• Molecular Mass: 331.38618
• Monoisotopic Mass: 331.08782903
• SMILES: c1ccc(cc1)COC(=O)N[C@@H](CSc1ccccc1)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)CSc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C17H17NO4S/c19-16(20)15(12-23-14-9-5-2-6-10-14)18-17(21)22-11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m0/s1
• InChIKey: ISBOGFMUFMJWEP-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(benzyloxy)carbonyl]amino}-3-(phenylsulfanyl)propanoic acid
• IUPAC Traditional name: (2R)-2-{[(benzyloxy)carbonyl]amino}-3-(phenylsulfanyl)propanoic acid
• Synonyms: N-Z-S-phenyl-L-cysteine; S-Phenyl-N-[(phenylmethoxy)carbonyl]-L-cysteine; N-Benzyloxycarbonyl-S-phenyl-L-cysteine; N-Carbobenzoxy-S-phenyl-L-cysteine; N-Carbobenzoxy-S-phenylcysteine; N-Carbobenzyloxy-3-phenylthio-L-alanine; N-Z-S-苯基-L-半胱氨酸

Database IDs

• CAS Number: 159453-24-4
• MDL Number: MFCD00671699
• PubChem SID: 24877732; 162239461
• PubChem CID: 2733947

CALCULATED PROPERTIES

• Acid pKa: 3.725291
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6229725
• LogD (pH = 7.4): 0.10223749
• Log P: 3.397344
• Molar Refractivity: 88.4798 cm^3
• Polarizability: 34.593166 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane
• Apperance: Colourless Thick Oil
• Melting Point: 94-97 °C(lit.)
• Optical Rotation: [α]20/D -55°, c = 2 in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C17H17NO4S

DETAILS

Sigma Aldrich - 530166

Packaging
25 g in glass bottle

REFERENCES

• Kaldor, S., et al.: J. Med. Chem., 40, 3979 (1997)