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

• ChemBase ID: 156473
• Molecular Formular: C20H32O5
• Molecular Mass: 352.46508
• Monoisotopic Mass: 352.22497412
• SMILES: CCCCC[C@@H](C=C[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C/CCCC(=O)O)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1C(=O)C[C@@H]([C@@H]1C/C=C/CCCC(=O)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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,18-/m0/s1
• InChIKey: BHMBVRSPMRCCGG-MLHJIOFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
• Synonyms: (5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic-acid; PGD2; Prostaglandin D2

Database IDs

• CAS Number: 41598-07-6
• MDL Number: MFCD00077857
• Beilstein Number: 2170623
• PubChem SID: 162250611
• PubChem CID: 71312324

CALCULATED PROPERTIES

• Acid pKa: 4.4045534
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.0978866
• LogD (pH = 7.4): 0.34078184
• 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

Safety Information

• RTECS: UK7930000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-22
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, 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: ≥96.0% (TLC)
• Empirical Formula (Hill Notation): C20H32O5

DETAILS

Sigma Aldrich - 82469

Biochem/physiol Actions
Primary prostaglandin in brain; induces inflammation; stimulates adenylyl cyclase.
Other Notes
Binding, conversion and metabolic effect of PGD2 on parenchymal liver cells.1