(5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid

• ChemBase ID: 164921
• Molecular Formular: C22H29ClO6
• Molecular Mass: 424.91506
• Monoisotopic Mass: 424.16526633
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)/C=C/[C@H](COc1cc(ccc1)Cl)O)C/C=C\CCCC(=O)O
• Canonical SMILES: OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](COc1cccc(c1)Cl)O)O
• InChI: InChI=1S/C22H29ClO6/c23-15-6-5-7-17(12-15)29-14-16(24)10-11-19-18(20(25)13-21(19)26)8-3-1-2-4-9-22(27)28/h1,3,5-7,10-12,16,18-21,24-26H,2,4,8-9,13-14H2,(H,27,28)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
• InChIKey: VJGGHXVGBSZVMZ-QIZQQNKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: (5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid
• Synonyms: (5Z)-rel-7-[(1R,2R,3R,5S)-2-[(1E,3S)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic Acid; Ciosin; Estrumat; Estrumate; ICI 80996; Planate; Cloprostenol

Database IDs

• CAS Number: 206555-98-8
• PubChem SID: 162259055
• PubChem CID: 5311053

CALCULATED PROPERTIES

• Acid pKa: 4.3552938
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.4731349
• LogD (pH = 7.4): -0.2759445
• Log P: 2.6461124
• Molar Refractivity: 112.7521 cm^3
• Polarizability: 43.546616 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C587300

Aryl-oxymethyl analog of prostaglandin F2α.

REFERENCES

• Binder, D., et al.: Prostaglandins, 6, 87 (1974)
• Bourne, G.R., et al.: Xenobiotica, 9, 623 (1974)
• Baishya, N., et al.: Br. Vet. J., et al.: 136, 227 (1974)
• Whyman, D., et al.: J. Reprod. Fertil., 60, 267 (1974)