(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide

• ChemBase ID: 162052
• Molecular Formular: C25H37NO4
• Molecular Mass: 415.56558
• Monoisotopic Mass: 415.27225867
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)/C=C/[C@@H](CCc1ccccc1)O)C/C=C\CCCC(=O)NCC
• Canonical SMILES: CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@@H](CCc1ccccc1)O)O
• InChI: InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21-,22-,23+,24-/m1/s1
• InChIKey: AQOKCDNYWBIDND-ZPFRTTICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
• IUPAC Traditional name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide; (15R)-Bimatoprost

Database IDs

• CAS Number: 1163135-92-9
• PubChem SID: 162256187
• PubChem CID: 52193994

CALCULATED PROPERTIES

• Acid pKa: 14.34702
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 2.6292617
• LogD (pH = 7.4): 2.6292624
• Log P: 2.6292624
• Molar Refractivity: 122.8312 cm^3
• Polarizability: 47.097137 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B386815

An intermediate in the production of Bimatoprost (B386800).