ethyl (2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoate

• ChemBase ID: 161304
• Molecular Formular: C18H19NO4
• Molecular Mass: 313.34776
• Monoisotopic Mass: 313.13140809
• SMILES: c1cccc(c1)[C@@H]([C@@H](O)C(=O)OCC)NC(=O)c1ccccc1
• Canonical SMILES: CCOC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O
• InChI: InChI=1S/C18H19NO4/c1-2-23-18(22)16(20)15(13-9-5-3-6-10-13)19-17(21)14-11-7-4-8-12-14/h3-12,15-16,20H,2H2,1H3,(H,19,21)/t15-,16+/m0/s1
• InChIKey: OQAQLARGRIIKCB-JKSUJKDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoate
• IUPAC Traditional name: ethyl (2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoate
• Synonyms: (αR,βS)-β-(Benzoylamino)-α-hydroxybenzenepropanoic Acid Ethyl Ester; Ethyl (2R,3S)-3-(Benzoylamino)-2-hydroxybenzenepropanoate; (2R,3S)-N-Benzoyl-3-phenyl Isoserine Ethyl Ester

Database IDs

• CAS Number: 153433-80-8
• PubChem SID: 162255439
• PubChem CID: 9883276

CALCULATED PROPERTIES

• Acid pKa: 12.006202
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.3343418
• LogD (pH = 7.4): 2.3343313
• Log P: 2.334342
• Molar Refractivity: 85.9558 cm^3
• Polarizability: 33.348095 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B208555

(2R,3S)-N-Benzoyl-3-phenylisoserine ethyl ester is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine ethyl ester shows cytotoxic, antivira

REFERENCES

• Paal, K. et al.: Bioorg. Med. Chem., 15, 1323 (2007)
• Krawczyk, E. et al.: J. Pharm. Pharmacol., 57, 791 (2007)