prop-2-en-1-yl (2S,3R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-hydroxybutanoate

• ChemBase ID: 169340
• Molecular Formular: C22H23NO5
• Molecular Mass: 381.42172
• Monoisotopic Mass: 381.15762284
• SMILES: [C@@H]([C@H](NC(=O)OCC1c2c(c3c1cccc3)cccc2)C(=O)OCC=C)(O)C
• Canonical SMILES: C=CCOC(=O)[C@H]([C@H](O)C)NC(=O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C22H23NO5/c1-3-12-27-21(25)20(14(2)24)23-22(26)28-13-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h3-11,14,19-20,24H,1,12-13H2,2H3,(H,23,26)/t14-,20+/m1/s1
• InChIKey: GLXCMMPBFKKXPV-VLIAUNLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (2S,3R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-hydroxybutanoate
• IUPAC Traditional name: prop-2-en-1-yl (2S,3R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-hydroxybutanoate
• Synonyms: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-threonine 2-Propen-1-yl Ester; N-(9-Fluorenylmethoxycarbonyl)threonine Allyl Ester; N-Fmoc-L-threonine Allyl Ester

Database IDs

• CAS Number: 136523-92-7
• PubChem SID: 162263472
• PubChem CID: 11474494

CALCULATED PROPERTIES

• Acid pKa: 13.3052225
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.292126
• LogD (pH = 7.4): 3.2921255
• Log P: 3.292126
• Molar Refractivity: 104.4714 cm^3
• Polarizability: 41.993553 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F676000

Threonine derivative.

REFERENCES

• Maemura, M., et al.: Biosci. Biotechnol .Biochem., 69, 1575 (2005)