7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid

• ChemBase ID: 153125
• Molecular Formular: C20H34O5
• Molecular Mass: 354.48096
• Monoisotopic Mass: 354.24062419
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@H]2C[C@@H]([C@@H]1CCCCCCC(=O)O)OO2)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H]2OO[C@H]([C@@H]1CCCCCCC(=O)O)C2)O
• InChI: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h12-13,15-19,21H,2-11,14H2,1H3,(H,22,23)/t15-,16+,17+,18-,19+/m0/s1
• InChIKey: NTAYABHEVAQSJS-BRIYLRKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
• Synonyms: 9,11-epi-Dioxy-15-hydroxy-(9α,11α,13E,15S)-prost-13-en-1-oic acid; PGH1; Prostaglandin H1

Database IDs

• MDL Number: MFCD00084825
• PubChem SID: 162247265
• PubChem CID: 3246811

CALCULATED PROPERTIES

• Acid pKa: 4.405127
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.1919944
• LogD (pH = 7.4): 1.4348043
• Log P: 4.318849
• Molar Refractivity: 96.9253 cm^3
• Polarizability: 38.397274 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: acetone solution
• Flash Point: 1 °F; -17 °C

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1090
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 9-16-26
• RID/ADR: UN 1090 3/PG 2
• Storage Temperature: -70°C

Product Information

• Purity: >95% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C20H34O5

DETAILS

Sigma Aldrich - P6492

Biochem/physiol Actions
Aryl hydrocarbon receptor (AhR) ligand and activator of the AhR signal transduction pathway. Also acts as a modest ligand of the peroxisome proliferator-activated receptor (PPAR-γ).