(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

• ChemBase ID: 3506
• Molecular Formular: C20H32O6
• Molecular Mass: 368.46448
• Monoisotopic Mass: 368.21988874
• SMILES: C(=O)(CCC/C=C\C[C@H]1[C@@H]2C[C@H]([C@@H]1/C=C/[C@H](CCCCC)OO)OO2)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H]2OO[C@H]([C@@H]1C/C=C\CCCC(=O)O)C2)OO
• InChI: InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
• InChIKey: SGUKUZOVHSFKPH-YNNPMVKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
• IUPAC Traditional name: prostaglandin G2
• Synonyms: Prostaglandin G2

Database IDs

• PubChem SID: 160966945; 46509030
• PubChem CID: 5280883

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.3552938
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.2332852
• LogD (pH = 7.4): 1.4841852
• Log P: 4.406263
• Molar Refractivity: 99.3921 cm^3
• Polarizability: 38.86798 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.31
• LOG S: -4.15
• Solubility (Water): 2.64e-02 g/l

DETAILS

DrugBank - DB03866

• Drug Groups: experimental
• Description: A cyclic endoperoxide intermediate produced by the action of CYCLOOXYGENASE on ARACHIDONIC ACID. It is further converted by a series of specific enzymes to the series 2 prostaglandins. [PubChem]