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

• ChemBase ID: 1821
• Molecular Formular: C20H32O5
• Molecular Mass: 352.46508
• Monoisotopic Mass: 352.22497412
• SMILES: C(=O)(CCC/C=C\C[C@H]1[C@H](CC(=O)[C@@H]1/C=C/[C@H](CCCCC)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)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
• InChIKey: BHMBVRSPMRCCGG-OUTUXVNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: prostaglandin d2
• Synonyms: (5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic-acid; PGD2; Prostaglandin D2; (5e,13e)-9,15-Dihydroxy-11-Oxoprosta-5,13-Dien-1-Oicacid

Database IDs

• CAS Number: 41598-07-6
• MDL Number: MFCD00077857
• Beilstein Number: 2170623
• PubChem SID: 46504574; 24898605; 160965276
• PubChem CID: 448457

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.12
• LOG S: -3.61
• Solubility (Water): 8.60e-02 g/l

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: ≥95%
• Biological Source: synthetic

DETAILS

DrugBank - DB02056

• Drug Groups: experimental
• Description: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects. [PubChem]

Sigma Aldrich - P5172

Biochem/physiol Actions
Primary prostaglandin in brain; induces inflammation; stimulates adenylyl cyclase.