7-[(1R,2R,3R)-3-hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-en-1-yl]-5-oxocyclopentyl]-N-methanesulfonylhept-5-enamide

• ChemBase ID: 153800
• Molecular Formular: C23H31NO7S
• Molecular Mass: 465.55974
• Monoisotopic Mass: 465.18212334
• SMILES: CS(=O)(=O)NC(=O)CCC/C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=C[C@H](COc1ccccc1)O
• Canonical SMILES: O=C(NS(=O)(=O)C)CCC/C=C/C[C@H]1C(=O)C[C@H]([C@@H]1C=C[C@H](COc1ccccc1)O)O
• InChI: InChI=1S/C23H31NO7S/c1-32(29,30)24-23(28)12-8-3-2-7-11-19-20(22(27)15-21(19)26)14-13-17(25)16-31-18-9-5-4-6-10-18/h2,4-7,9-10,13-14,17,19-20,22,25,27H,3,8,11-12,15-16H2,1H3,(H,24,28)/t17-,19-,20-,22-/m1/s1
• InChIKey: UQZVCDCIMBLVNR-JWUVWSEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-en-1-yl]-5-oxocyclopentyl]-N-methanesulfonylhept-5-enamide
• IUPAC Traditional name: 7-[(1R,2R,3R)-3-hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-en-1-yl]-5-oxocyclopentyl]-N-methanesulfonylhept-5-enamide
• Synonyms: ZK-57671; Sulprostone; (5Z,11α,13E,15R)--11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide; CP-34089; SHB-286

Database IDs

• CAS Number: 60325-46-4
• EC Number: 262-173-0
• MDL Number: MFCD00216056
• PubChem SID: 162247939; 24724621
• PubChem CID: 71311734

CALCULATED PROPERTIES

• Acid pKa: 4.081759
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.49916926
• LogD (pH = 7.4): 0.39166096
• Log P: 1.3329879
• Molar Refractivity: 121.9008 cm^3
• Polarizability: 47.85182 Å^3
• Polar Surface Area: 130.0 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: colorless to yellow/brown oil

Safety Information

• RTECS: MJ8810000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-36/37/38
• Safety Statements: 53-22-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C23H31NO7S

DETAILS

Sigma Aldrich - S8692

Biochem/physiol Actions
Selective EP3 prostanoid receptor agonist.