7-[(1R,2S)-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid

• ChemBase ID: 156306
• Molecular Formular: C20H30O4
• Molecular Mass: 334.4498
• Monoisotopic Mass: 334.21440944
• SMILES: CCCCC[C@@H](C=C[C@H]1C=CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1C=CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O
• InChI: InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/t16-,17-,18+/m0/s1
• InChIKey: MYHXHCUNDDAEOZ-OKZBNKHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2S)-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1R,2S)-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
• Synonyms: (5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,10,13-trien-1-oic acid; PGA2; Prostaglandin A2 solution

Database IDs

• CAS Number: 13345-50-1
• MDL Number: MFCD00077859
• Beilstein Number: 2221844
• PubChem SID: 162250444
• PubChem CID: 71312291

CALCULATED PROPERTIES

• Acid pKa: 4.4020348
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.2462447
• LogD (pH = 7.4): 1.4895177
• Log P: 4.375951
• Molar Refractivity: 99.0899 cm^3
• Polarizability: 37.313618 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• 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
• 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), type ABEK (EN14387) respirator filter
• 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)
• Concentration: 10 mg/mL in methyl acetate
• Empirical Formula (Hill Notation): C20H30O4

DETAILS

Sigma Aldrich - 82472

Biochem/physiol Actions
Blocks cell cycle at G2/M; induces apoptosis in tumor cells; inhibits viral replication; PPARγ agonist.
Other Notes
Classification of prostaglandin receptors based on coupling to signal transduction systems1