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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H34O5
Molecular Weight 378.5024
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,9-DIDEOXYFORSKOLIN

SMILES

[H][C@@]12[C@H](O)[C@H](OC(C)=O)[C@@]3(C)O[C@](C)(CC(=O)[C@]3([H])[C@@]1(C)CCCC2(C)C)C=C

InChI

InChIKey=ZKZMDXUDDJYAIB-SUCLLAFCSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/16749796 | https://clinicaltrials.gov/ct2/show/NCT02143349 | https://www.ncbi.nlm.nih.gov/pubmed/2454506 | https://www.drugs.com/npp/forskolin.html | https://www.ncbi.nlm.nih.gov/pubmed/19831022

1,9-dideoxyforskolin from Coleus forskohlii (forskolin), a highly oxygenated labdane diterpenoid is an activator of adenylate cyclase. An extract of the plant Coleus forskohlii has been used for centuries in Ayurvedic medicine to treat various diseases such as hypothyroidism, heart disease, and respiratory disorders. Preliminary studies have shown that forskolin can increase fat metabolism thus reduce fat accumulation in both animals and humans. Coleus forskohlii extract and forskolin extract were investigated for treatment obesity and in preventing asthma attacks in patients with mild persistent or moderate persistent asthma. Extracted from the aerial parts of Coleus forskohlii forskolin was also found to be active against HIV(NL4-3). Forskolin can be synthesized in 12 steps (12% overall yield) from ptychantin A, which has been isolated from liverwort Ptychanthus striatus and is a widely used as a biochemical tool. It activates adenyl cyclase, thereby increasing intracellular concentration of cAMP and thus activating the protein kinase A (PKA) signal transduction pathway. PKA-dependent and -independent effects of forskolin on the expression of drug-metabolizing enzymes in liver suggested that herbal therapy with C. forskohlii extract should be approached cautiously due to the potential for herb-drug interactions in patients on combination therapy.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Direct anesthetic-like effects of forskolin on the nicotinic acetylcholine receptors of PC12 cells.
1986 Mar 5
Effect of forskolin on voltage-gated K+ channels is independent of adenylate cyclase activation.
1988 Jun 17
Differential identification and localization of adenylyl cyclase and glucose transporter in brain using iodinated derivatives of forskolin.
1992 May 22
The expression and regulation of depolarization-activated K+ channels in the insulin-secreting cell line INS-1.
2001 Apr
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.
2001 Feb
Functional characterisation of the volume-sensitive anion channel in rat pancreatic beta-cells.
2001 Mar
Characterization of the taurine transport pathway in A6 kidney cells.
2002 Nov 15
Extracellular acidification elicits a chloride current that shares characteristics with ICl(swell).
2004 Nov
Analysis of glycoproteins in human colon cancers, normal tissues and in human colon carcinoma cells reactive with monoclonal antibody NCL-19-9.
2005 Sep
Synthetic transformation of ptychantin into forskolin and 1,9-dideoxyforskolin.
2006 Jun 9
Ca2+-independent, inhibitory effects of cyclic adenosine 5'-monophosphate on Ca2+ regulation of phosphoinositide 3-kinase C2alpha, Rho, and myosin phosphatase in vascular smooth muscle.
2007 Feb
Tamoxifen does not inhibit the swell activated chloride channel in human neutrophils during the respiratory burst.
2008 Oct 31
The adenylyl cyclase-cAMP system suppresses TARC/CCL17 and MDC/CCL22 production through p38 MAPK and NF-kappaB in HaCaT keratinocytes.
2009 Jun
Anti-HIV diterpenes from Coleus forskohlii.
2009 Sep
Extracellular osmolarity modulates G protein-coupled receptor-dependent ATP release from 1321N1 astrocytoma cells.
2010 Feb

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
10 uM 1,9-dideoxyforskolin inhibited carbachol-stimulated 86Rb+ uptake in C12 cells by approximately 80%.
Name Type Language
1,9-DIDEOXYFORSKOLIN
Common Name English
(-)-1,9-DIDEOXYFORSKOLIN
Common Name English
1H-NAPHTHO(2,1-B)PYRAN-1-ONE, 5-(ACETYLOXY)-3-ETHENYLDODECAHYDRO-6-HYDROXY-3,4A,7,7,10A-PENTAMETHYL-, (3R,4AS,5S,6S,6AS,10AS,10BR)-
Systematic Name English
1,9-DIDEOXYFORSKOLIN, (-)-
Common Name English
Code System Code Type Description
PUBCHEM
107948
Created by admin on Sat Dec 16 08:45:44 GMT 2023 , Edited by admin on Sat Dec 16 08:45:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID5040384
Created by admin on Sat Dec 16 08:45:44 GMT 2023 , Edited by admin on Sat Dec 16 08:45:44 GMT 2023
PRIMARY
CAS
64657-18-7
Created by admin on Sat Dec 16 08:45:44 GMT 2023 , Edited by admin on Sat Dec 16 08:45:44 GMT 2023
PRIMARY
FDA UNII
OAW710HWIX
Created by admin on Sat Dec 16 08:45:44 GMT 2023 , Edited by admin on Sat Dec 16 08:45:44 GMT 2023
PRIMARY