8-[(1R,5R)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]octanoic acid

• ChemBase ID: 176106
• Molecular Formular: C18H28O3
• Molecular Mass: 292.41312
• Monoisotopic Mass: 292.20384476
• SMILES: C1=C[C@H]([C@H](C1=O)C/C=C\CC)CCCCCCCC(=O)O
• Canonical SMILES: CC/C=C\C[C@@H]1[C@H](CCCCCCCC(=O)O)C=CC1=O
• InChI: InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16-/m1/s1
• InChIKey: PMTMAFAPLCGXGK-GTOOTHNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(1R,5R)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]octanoic acid
• IUPAC Traditional name: 12-oxo-pda
• Synonyms: (1R,5R)-rel-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-octanoic Acid; [1α,5α(Z)]-(+/-)-4-Oxo-5-(2-pentenyl)-2-cyclopentene-1-octanoic Acid; (+/-)-12-Oxophytodienoic Acid; rac 12-Oxophytodienoic Acid

Database IDs

• CAS Number: 85551-10-6
• PubChem SID: 164232016
• PubChem CID: 5282268

CALCULATED PROPERTIES

• Acid pKa: 4.7845836
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.288313
• LogD (pH = 7.4): 2.5130265
• Log P: 5.0795465
• Molar Refractivity: 87.2558 cm^3
• Polarizability: 33.251522 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O870200

The octadecanoid 12-oxo-phytodienoic acid (OPDA) is an intermediate in biosynthesis of jasmonic acid in plants. 12-Oxo-phytodienoic acid (OPDA)-induced expression changes in Arabidopsis by cDNA macroarray.

REFERENCES

• Laemmli, U., et al.: Nature, 227, 680 (1970)
• Palmgren, M., et al.: Plant Physiology, 90, 1009 (1970)
• Mueller, M., et al.: Anal. Biochem., 218, 425 (1970)