(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid

• ChemBase ID: 132187
• Molecular Formular: C20H34O5
• Molecular Mass: 354.48096
• Monoisotopic Mass: 354.24062419
• SMILES: CCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
• Canonical SMILES: CCCCCC(=O)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,18+,19-/m1/s1
• InChIKey: VKTIONYPMSCHQI-XAGFEHLVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 13,14-dihydro-15-keto-PGF2α
• Synonyms: 13,14-Dihydro-15-ketoprostaglandin F2α

Database IDs

• CAS Number: 27376-76-7
• MDL Number: MFCD00135243
• PubChem SID: 24893819; 162226464
• PubChem CID: 5283039

CALCULATED PROPERTIES

• Acid pKa: 4.3063054
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.8059256
• LogD (pH = 7.4): 0.06617563
• Log P: 3.0245695
• Molar Refractivity: 98.48 cm^3
• Polarizability: 38.432873 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 13
• 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 - D4143

Biochem/physiol Actions
Enzyme derived prostaglandin that acts as a hormone in uterine functions and may effect glucose uptake.