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

• ChemBase ID: 158418
• Molecular Formular: C20H32O5
• Molecular Mass: 352.46508
• Monoisotopic Mass: 352.22497412
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O
• InChI: InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1
• InChIKey: XEYBRNLFEZDVAW-DODZYUBVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
• Synonyms: (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid; Dinoprostone; PGE2; Prostaglandin E2

Database IDs

• CAS Number: 363-24-6
• EC Number: 206-656-6
• MDL Number: MFCD00077861
• Beilstein Number: 4709356
• PubChem SID: 162252554
• PubChem CID: 49822699

CALCULATED PROPERTIES

• Acid pKa: 4.3033595
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.0038702
• LogD (pH = 7.4): 0.2647247
• Log P: 3.22527
• Molar Refractivity: 99.4351 cm^3
• Polarizability: 38.188305 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble10 mg/mL, clear, colorless to faintly yellow

Safety Information

• RTECS: UK8000000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-61-22
• Safety Statements: 53-22-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C20H32O5

DETAILS

Sigma Aldrich - 82475

Other Notes
Differential effect of PGE2 on transforming growth factor-β, and insulin-induced collagen formation in lung fibroblasts2
Biochem/physiol Actions
Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.1