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

• ChemBase ID: 105515
• Molecular Formular: C22H34O7
• Molecular Mass: 410.50116
• Monoisotopic Mass: 410.23045343
• SMILES: C=C[C@@]1(C)CC(=O)[C@@]2([C@@]3(C)[C@H](CCC(C)(C)C3[C@@H]([C@@H]([C@@]2(C)O1)OC(=O)C)O)O)O
• Canonical SMILES: C=C[C@@]1(C)CC(=O)[C@]2([C@@](O1)(C)[C@@H](OC(=O)C)[C@H](C1[C@]2(C)[C@@H](O)CCC1(C)C)O)O
• InChI: InChI=1S/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16?,17-,19-,20-,21+,22-/m0/s1
• InChIKey: OHCQJHSOBUTRHG-VDCUXWMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4aR,5S,6S,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
• IUPAC Traditional name: (3R,4aR,5S,6S,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2H-naphtho[2,1-b]pyran-5-yl acetate
• Synonyms: FORSKOLIN

Database IDs

• CAS Number: 66575-29-9
• EC Number: 266-410-9
• PubChem SID: 162093617
• PubChem CID: 5702265

CALCULATED PROPERTIES

• Acid pKa: 11.565541
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.3561152
• LogD (pH = 7.4): 1.356086
• Log P: 1.3561156
• Molar Refractivity: 104.4681 cm^3
• Polarizability: 42.281574 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 228-230°C

Safety Information

• Storage Condition: 0°C, Desiccate
• RTECS: QL6150000

DETAILS

MP Biomedicals - 02194803

From Coleus forskohlii
(7 β-acetoxy-8,13-epoxy-1α,6 β,9α-trihydroxy-labd-14-ene-11-one)
Molecular Biology Reagent
Functions as an antihypertensive and vasodilator. Adenylcyclase activator.

MP Biomedicals - 02190669

From Coleus forskohlii (7β-acetoxy-8,13-epoxy-1a,6β,9a-trihydroxy-labd-14-ene-11-one)
Reported to demonstrate positive inotropic and heart rate-increasing activity at low doses in animals. Also functions as an antihypertensive and vasodilator at higher doses. Activates adenylcyclase in rat liver membranes.

REFERENCES

• Huang, R., et al., J. Cyclic Nucleotide Research, 8 : 385 (1982).
• H. Metzger and E.Lindner, I.R.C.S. Med. Sci., Biochem., Cardiovascular System Pharm., 9: 99 (1981).