(3R,4aS,5S,6S,6aS,10aS)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate

• ChemBase ID: 133271
• Molecular Formular: C22H34O5
• Molecular Mass: 378.50236
• Monoisotopic Mass: 378.24062419
• SMILES: CC(=O)O[C@H]1[C@H]([C@@H]2[C@](CCCC2(C)C)(C2[C@@]1(O[C@@](CC2=O)(C)C=C)C)C)O
• Canonical SMILES: C=C[C@@]1(C)CC(=O)C2[C@@](O1)(C)[C@@H](OC(=O)C)[C@H]([C@@H]1[C@]2(C)CCCC1(C)C)O
• InChI: InChI=1S/C22H34O5/c1-8-20(5)12-14(24)16-21(6)11-9-10-19(3,4)17(21)15(25)18(26-13(2)23)22(16,7)27-20/h8,15-18,25H,1,9-12H2,2-7H3/t15-,16?,17-,18-,20-,21+,22-/m0/s1
• InChIKey: ZKZMDXUDDJYAIB-OJPJTMFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4aS,5S,6S,6aS,10aS)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
• IUPAC Traditional name: (3R,4aS,5S,6S,6aS,10aS)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-octahydronaphtho[2,1-b]pyran-5-yl acetate
• Synonyms: 7β-Acetoxy-6β-hydroxy-8,13-epoxy-labd-14-en-11-one; 1,9-Dideoxyforskolin from Coleus forskohlii

Database IDs

• CAS Number: 64657-18-7
• MDL Number: MFCD00082318
• PubChem SID: 24893774; 162227548
• PubChem CID: 10452268

CALCULATED PROPERTIES

• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 13.803038
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.1784444
• LogD (pH = 7.4): 3.1784441
• Log P: 3.1784444
• Molar Refractivity: 101.7066 cm^3
• Polarizability: 40.983833 Å^3

PROPERTIES

Physical Property

• Solubility: dilute aqueous acid and base: insoluble; DMSO: soluble3 mg/mL; ethanol: soluble6.6 mg/mL; methanol: soluble28 mg/mL
• Apperance: white solid
• Optical Rotation: [α]26/D +93.6°, c = 6.12 in chloroform(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97%

DETAILS

Sigma Aldrich - D3658

Application
Useful as a negative control for forskolin.
Biochem/physiol Actions
Biologically inactive forskolin analog. Does not stimulate adenylyl cyclase.