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
SMILES
CC(=O)O[C@H]1[C@@H](O)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]3C(=O)C[C@@](C)(O[C@]13C)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
| Molecular Formula | C22H34O5 |
| Molecular Weight | 378.5024 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1287276
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1287276
1,9-Dideoxyforskolin (DFK) is an inhibitor of glucose transporter, has been synthesized in 8 steps and 37% overall yield. 1,9-Dideoxyforskolin is a biologically inactive forskolin analog and does not stimulate adenylyl cyclase. DFK mimics some activity of forskolin, demonstrating alteration of K+ channel activity, reversal of doxorubicin resistance in multidrug resistant sarcoma cells, protection against TNF-α-mediated cytotoxicity, and desensitization at GABAA receptors. The inhibitory effect of DFK on high K (+)-induced contraction was antagonized by an increase in extracellular Ca2+ concentration. DFK inhibited the increase in cytosolic Ca2+ level and contraction in parallel whereas forskolin inhibited the contraction more strongly than the cytosolic Ca2+ level. These results suggest that DFK, but not forskolin, inhibits vascular smooth muscle contraction by a Ca2+ channel blocker-like action.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of Coleus forskohlii and its major constituents on cytochrome P450 induction. | 2016-01 |
|
| Extracellular osmolarity modulates G protein-coupled receptor-dependent ATP release from 1321N1 astrocytoma cells. | 2010-02 |
|
| Anti-HIV diterpenes from Coleus forskohlii. | 2009-09 |
|
| The adenylyl cyclase-cAMP system suppresses TARC/CCL17 and MDC/CCL22 production through p38 MAPK and NF-kappaB in HaCaT keratinocytes. | 2009-06 |
|
| Tamoxifen does not inhibit the swell activated chloride channel in human neutrophils during the respiratory burst. | 2008-10-31 |
|
| 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. | 2007-02 |
|
| Synthetic transformation of ptychantin into forskolin and 1,9-dideoxyforskolin. | 2006-06-09 |
|
| Block of spontaneous termination of paroxysmal depolarizations by forskolin (buccal ganglia, Helix pomatia). | 2006-01-09 |
|
| Analysis of glycoproteins in human colon cancers, normal tissues and in human colon carcinoma cells reactive with monoclonal antibody NCL-19-9. | 2005-09 |
|
| Induction of drug metabolism by forskolin: the role of the pregnane X receptor and the protein kinase a signal transduction pathway. | 2005-02 |
|
| Extracellular acidification elicits a chloride current that shares characteristics with ICl(swell). | 2004-11 |
|
| Apoptosis to necrosis switching downstream of apoptosome formation requires inhibition of both glycolysis and oxidative phosphorylation in a BCL-X(L)- and PKB/AKT-independent fashion. | 2004-03 |
|
| PKA modulation of Kv4.2-encoded A-type potassium channels requires formation of a supramolecular complex. | 2002-12-01 |
|
| Characterization of the taurine transport pathway in A6 kidney cells. | 2002-11-15 |
|
| The adenylate cyclase activator forskolin partially protects L929 cells against tumour necrosis factor-alpha-mediated cytotoxicity via a cAMP-independent mechanism. | 2002-09-07 |
|
| Molecular identification of P-glycoprotein: a role in lens circulation? | 2002-09 |
|
| The expression and regulation of depolarization-activated K+ channels in the insulin-secreting cell line INS-1. | 2001-04 |
|
| Functional characterisation of the volume-sensitive anion channel in rat pancreatic beta-cells. | 2001-03 |
|
| Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex. | 2001-02 |
|
| Catecholaminergic regulation of Na-K-Cl cotransport in pigmented ciliary epithelium: differences between PE and NPE. | 2001-01 |
|
| Differential identification and localization of adenylyl cyclase and glucose transporter in brain using iodinated derivatives of forskolin. | 1992-05-22 |
|
| Effect of forskolin on voltage-gated K+ channels is independent of adenylate cyclase activation. | 1988-06-17 |
|
| Partial reversal of doxorubicin resistance by forskolin and 1,9-dideoxyforskolin in murine sarcoma S180 variants. | 1988-02-01 |
|
| Direct anesthetic-like effects of forskolin on the nicotinic acetylcholine receptors of PC12 cells. | 1986-03-05 |
|
| Forskolin: unique diterpene activator of adenylate cyclase in membranes and in intact cells. | 1981-06 |
Sample Use Guides
250 mg of a 10% forskolin extract twice daily for 12 weeks has been studied in obesity. Oral forskolin has been studied using 10 mg daily over 2 to 6 months in asthma
Route of Administration:
Oral
Treatment with low concentrations (1 uM) of forskolin produced robust induction of CYP3A gene expression in wild-type mouse hepatocytes but not in PXR knockout hepatocytes. Treatment of hepatocytes with higher concentrations of forskolin (10 and 100 uM) produced very modest levels of CYP3A gene expression in PXR knockout hepatocytes when compared with that achieved in wild-type hepatocytes.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 22:17:50 GMT 2025
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admin
on
Mon Mar 31 22:17:50 GMT 2025
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| Record UNII |
OAW710HWIX
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID5040384
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64657-18-7
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OAW710HWIX
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admin on Mon Mar 31 22:17:50 GMT 2025 , Edited by admin on Mon Mar 31 22:17:50 GMT 2025
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