methyl (2Z,4E)-5-[(1R,6R)-6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate

• ChemBase ID: 158819
• Molecular Formular: C17H20O4
• Molecular Mass: 288.3383
• Monoisotopic Mass: 288.13615912
• SMILES: [C@]1(CC(=O)C=C([C@]1(O)/C=C/C(=C\C(=O)OC)/C)C)(C#C)C
• Canonical SMILES: COC(=O)/C=C(\C=C\[C@@]1(O)C(=CC(=O)C[C@]1(C)C#C)C)/C
• InChI: InChI=1S/C17H20O4/c1-6-16(4)11-14(18)10-13(3)17(16,20)8-7-12(2)9-15(19)21-5/h1,7-10,20H,11H2,2-5H3/b8-7+,12-9-/t16-,17+/m0/s1
• InChIKey: AIBVECHZVPKHDS-JQOGSSFGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2Z,4E)-5-[(1R,6R)-6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate
• IUPAC Traditional name: methyl (2Z,4E)-5-[(1R,6R)-6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate
• Synonyms: (2Z,4E)-rel-5-[(1R,6R)-6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic Acid Methyl Ester; PBI 429; rac 8'-Acetylene Abscisic Acid Methyl Ester

Database IDs

• CAS Number: 192987-96-5
• PubChem SID: 162252954
• PubChem CID: 71312703

CALCULATED PROPERTIES

• Acid pKa: 13.094353
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.1099167
• LogD (pH = 7.4): 2.109916
• Log P: 2.1099167
• Molar Refractivity: 82.8081 cm^3
• Polarizability: 30.951439 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A110010

Abscisic acid analog used to enhance growth control in plants.

REFERENCES

• Berkowitz, G., et al.: Plant Physiol., 86, 329 (1988)
• Churchill, G., et al.: Plant Growth Regul., 25, 35 (1988)
• Cutler, A., et al.: Biochem. 39, 13614 (1988)