Forskolin

Status : experimental

Description

Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant Coleus forskohlii. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland. [PubChem]

Chemical Classification

This compound belongs to the class of organic compounds known as naphthopyrans. These are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Naphthopyrans

Organic compounds

Organoheterocyclic compounds

Naphthopyrans

Calculated Property

kind Value Source
logP 1.28 ALOGPS
logS -2.6 ALOGPS
Water Solubility 1.10e+00 g/l ALOGPS
logP 1.36 ChemAxon
IUPAC Name (3R,4aR,5S,6S,6aS,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 ChemAxon
Traditional IUPAC Name forskolin ChemAxon
Molecular Weight 410.5012 ChemAxon
Monoisotopic Weight 410.230453442 ChemAxon
SMILES [H][C@]1(O)CCC(C)(C)[C@]2([H])[C@]([H])(O)[C@]([H])(OC(C)=O)[C@@]3(C)O[C@](C)(CC(=O)[C@]3(O)[C@@]12C)C=C ChemAxon
Molecular Formula C22H34O7 ChemAxon
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 ChemAxon
InChIKey InChIKey=OHCQJHSOBUTRHG-KGGHGJDLSA-N ChemAxon
Polar Surface Area (PSA) 113.29 ChemAxon
Refractivity 104.47 ChemAxon
Polarizability 43.33 ChemAxon
Rotatable Bond Count 3 ChemAxon
H Bond Acceptor Count 6 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 11.57 ChemAxon
pKa (strongest basic) -3 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • Adenylate cyclase type 2 : in Human
  • Guanine nucleotide-binding protein G(s) subunit alpha isoforms short : in Human
  • Adenylate cyclase type 5 : in Human