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Identification
NameForskolin
Accession NumberDB02587  (EXPT01467)
Typesmall molecule
Groupsexperimental
Description

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

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number64657-11-0
WeightAverage: 410.5012
Monoisotopic: 410.230453442
Chemical FormulaC22H34O7
InChI KeyOHCQJHSOBUTRHG-KGGHGJDLSA-N
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
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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassPrenol Lipids
SubclassDiterpenes
Direct parentDiterpenes
Alternative parentsNaphthopyrans; Naphthalenes; Cyclohexanols; Pyrans; Oxanes; Tertiary Alcohols; Carboxylic Acid Esters; Ketones; Cyclic Alcohols and Derivatives; Polyols; Enolates; Ethers; Polyamines
Substituentsacene; naphthalene; cyclohexanol; oxane; pyran; cyclic alcohol; tertiary alcohol; polyol; secondary alcohol; carboxylic acid ester; ketone; enolate; ether; polyamine; carboxylic acid derivative; carbonyl group; alcohol
Classification descriptionThis compound belongs to the diterpenes. These are terpene compounds formed by four isoprene units.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.6195
Blood Brain Barrier + 0.6888
Caco-2 permeable - 0.6796
P-glycoprotein substrate Substrate 0.8361
P-glycoprotein inhibitor I Inhibitor 0.8198
P-glycoprotein inhibitor II Inhibitor 0.6788
Renal organic cation transporter Non-inhibitor 0.8998
CYP450 2C9 substrate Non-substrate 0.7961
CYP450 2D6 substrate Non-substrate 0.892
CYP450 3A4 substrate Substrate 0.7016
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.935
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Inhibitor 0.7959
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9606
Ames test Non AMES toxic 0.6284
Carcinogenicity Non-carcinogens 0.9539
Biodegradation Not ready biodegradable 0.9792
Rat acute toxicity 2.2384 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9911
hERG inhibition (predictor II) Non-inhibitor 0.8782
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.10e+00 g/lALOGPS
logP1.28ALOGPS
logP1.36ChemAxon
logS-2.6ALOGPS
pKa (strongest acidic)11.57ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count3ChemAxon
polar surface area113.29ChemAxon
rotatable bond count3ChemAxon
refractivity104.47ChemAxon
polarizability43.33ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Emiko Yamasaki, Takaaki Ohkuma, “Lyophilized preparation of 6-(3-dimethylaminopropionyl)forskolin.” U.S. Patent US5051132, issued June, 1974.

US5051132
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound47936
PubChem Substance46509044
ChemSpider43607
ChEBI42471
ChEMBL
PharmGKBPA146096022
HETFOK
Drugs.comhttp://www.drugs.com/npc/forskolin.html
WikipediaForskolin
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Adenylate cyclase type 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenylate cyclase type 2 Q08462 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Guanine nucleotide-binding protein G(s) subunit alpha isoforms short

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short P63092 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Adenylate cyclase type 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenylate cyclase type 5 O95622 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18