(5Z)-7-[(1S,4R,5S,6R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-oxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid

• ChemBase ID: 133186
• Molecular Formular: C21H34O4
• Molecular Mass: 350.49226
• Monoisotopic Mass: 350.24570957
• SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)OC2)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H]2CO[C@H]([C@@H]1C/C=C\CCCC(=O)O)C2)O
• InChI: InChI=1S/C21H34O4/c1-2-3-6-9-17(22)12-13-18-16-14-20(25-15-16)19(18)10-7-4-5-8-11-21(23)24/h4,7,12-13,16-20,22H,2-3,5-6,8-11,14-15H2,1H3,(H,23,24)/b7-4-,13-12+/t16-,17-,18-,19+,20-/m0/s1
• InChIKey: DJKDIKIDYDXHDD-IGUVKOCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1S,4R,5S,6R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-oxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid
• IUPAC Traditional name: (5Z)-7-[(1S,4R,5S,6R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-oxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid
• Synonyms: U44069; 9,11-Dideoxy-9α,11α-epoxymethanoprostaglandin F2α

Database IDs

• CAS Number: 56985-32-1
• MDL Number: MFCD00135237
• PubChem SID: 24893231; 162227463
• PubChem CID: 5311386

CALCULATED PROPERTIES

• Acid pKa: 4.355294
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.9096334
• LogD (pH = 7.4): 1.1605543
• Log P: 4.082611
• Molar Refractivity: 101.812 cm^3
• Polarizability: 39.287865 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 22-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Shipped in: dry ice

DETAILS

Sigma Aldrich - D0400

Biochem/physiol Actions
Prostaglandin F2α analogue; thromboxane A2/prostaglandin H2 mimetic.