sodium 7-[(1R,2R,3R,5S)-2-[(3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate hydrate

• ChemBase ID: 154278
• Molecular Formular: C22H30ClNaO7
• Molecular Mass: 464.91217
• Monoisotopic Mass: 464.15777526
• SMILES: c1cc(cc(c1)Cl)OC[C@@H](C=C[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C/CCCC(=O)[O-])O)O)O.O.[Na+]
• Canonical SMILES: [O-]C(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1C=C[C@H](COc1cccc(c1)Cl)O)O.O.[Na+]
• InChI: InChI=1S/C22H29ClO6.Na.H2O/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);;1H2/q;+1;/p-1/t16-,18-,19-,20+,21-;;/m1../s1
• InChIKey: ZEQHRVULQBYULU-BRFXSNOJSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 7-[(1R,2R,3R,5S)-2-[(3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate hydrate
• IUPAC Traditional name: sodium 7-[(1R,2R,3R,5S)-2-[(3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate hydrate
• Synonyms: (+/-)-16-(3-Chlorophenoxy)-9,11,15R-trihydroxy-17,18,19,20-tetranorprosta-5Z,13E-dien-1-oic acid sodium salt hydrate; (+/-)-Cloprostenol sodium salt hydrate

Database IDs

• CAS Number: 55028-72-3(anhydrous)
• EC Number: 259-439-3
• PubChem SID: 162248417; 24724446
• PubChem CID: 71311829

CALCULATED PROPERTIES

• Acid pKa: 4.3552938
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.4731349
• LogD (pH = 7.4): -0.2759445
• Log P: 2.6461124
• Molar Refractivity: 123.5892 cm^3
• Polarizability: 43.43382 Å^3
• Polar Surface Area: 110.05 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: light brown powder
• Melting Point: 68-70 °C

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-22-36/37/38
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335-H361
• GHS Precautionary statements: P261-P281-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H28ClNaO6 · xH2O

DETAILS

Sigma Aldrich - C6116

Biochem/physiol Actions
Cloprostenol is a potent FP prostanoid receptor agonist. It is 2- to 3-fold more potent than fluprostenol but less selective. Cloprostenol is similar in potency to PGF2α at EP and TP prostanoid receptors. It is used for the treatment of infertility in sows and gilts.