7-[(1S)-5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

• ChemBase ID: 153720
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: CCCCC/C=C/C=C/1\[C@H](C=CC1=O)C/C=C/CCCC(=O)O
• Canonical SMILES: CCCCC/C=C/C=C/1\[C@@H](C/C=C/CCCC(=O)O)C=CC1=O
• InChI: InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/t17-/m0/s1
• InChIKey: VHRUMKCAEVRUBK-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1S)-5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1S)-5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
• Synonyms: 11-Oxoprosta-(5Z,9,12E,14E)-tetraen-1-oic acid; 15-Deoxy-Δ12,14-PGJ2; 15-Deoxy-Δ12,14-prostaglandin J2

Database IDs

• CAS Number: 87893-55-8
• EC Number: 201-185-2
• MDL Number: MFCD00065806
• PubChem SID: 162247859
• PubChem CID: 12068863

CALCULATED PROPERTIES

• Acid pKa: 4.6585
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.5580964
• LogD (pH = 7.4): 2.780421
• Log P: 5.4571495
• Molar Refractivity: 98.4503 cm^3
• Polarizability: 36.457787 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: methyl acetate solution
• Flash Point: 15.8 °F; -9 °C

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1231
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 16-26-29-33
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H319-H336
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1231 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C20H28O3

DETAILS

Sigma Aldrich - D8440

Biochem/physiol Actions
Selective agonist to PPARγ (peroxisome proliferator-activated receptors). Inhibits the proliferation of cancer cell lines that express PPARγ and cyclooxygenase-2 (COX-2).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D8440.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.