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
[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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16749796https://www.ncbi.nlm.nih.gov/pubmed/15459237Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16749796https://www.ncbi.nlm.nih.gov/pubmed/15459237
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16091783 | https://www.ncbi.nlm.nih.gov/pubmed/1498664
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363032 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1287276 |
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Target ID: 1.04573632E8 Gene Symbol: ADCY1 |
5.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Partial reversal of doxorubicin resistance by forskolin and 1,9-dideoxyforskolin in murine sarcoma S180 variants. | 1988 Feb 1 |
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Differential identification and localization of adenylyl cyclase and glucose transporter in brain using iodinated derivatives of forskolin. | 1992 May 22 |
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Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex. | 2001 Feb |
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PKA modulation of Kv4.2-encoded A-type potassium channels requires formation of a supramolecular complex. | 2002 Dec 1 |
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Molecular identification of P-glycoprotein: a role in lens circulation? | 2002 Sep |
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The adenylate cyclase activator forskolin partially protects L929 cells against tumour necrosis factor-alpha-mediated cytotoxicity via a cAMP-independent mechanism. | 2002 Sep 7 |
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Extracellular acidification elicits a chloride current that shares characteristics with ICl(swell). | 2004 Nov |
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Analysis of glycoproteins in human colon cancers, normal tissues and in human colon carcinoma cells reactive with monoclonal antibody NCL-19-9. | 2005 Sep |
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Tamoxifen does not inhibit the swell activated chloride channel in human neutrophils during the respiratory burst. | 2008 Oct 31 |
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The adenylyl cyclase-cAMP system suppresses TARC/CCL17 and MDC/CCL22 production through p38 MAPK and NF-kappaB in HaCaT keratinocytes. | 2009 Jun |
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Anti-HIV diterpenes from Coleus forskohlii. | 2009 Sep |
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Extracellular osmolarity modulates G protein-coupled receptor-dependent ATP release from 1321N1 astrocytoma cells. | 2010 Feb |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3005280
10 uM 1,9-dideoxyforskolin inhibited carbachol-stimulated 86Rb+ uptake in C12 cells by approximately 80%.
Substance Class |
Chemical
Created
by
admin
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Edited
Sat Dec 16 08:45:44 GMT 2023
by
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Sat Dec 16 08:45:44 GMT 2023
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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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