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66428-89-5 molecular structure
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(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

ChemBase ID: 2315
Molecular Formular: C22H34O7
Molecular Mass: 410.50116
Monoisotopic Mass: 410.23045343
SMILES and InChIs

SMILES:
[C@H]1(O)CCC([C@@H]2[C@H](O)[C@H](OC(=O)C)[C@]3(O[C@](CC(=O)[C@]3(O)[C@@]12C)(C=C)C)C)(C)C
Canonical SMILES:
C=C[C@@]1(C)CC(=O)[C@]2([C@@](O1)(C)[C@@H](OC(=O)C)[C@H]([C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C)O)O
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
InChIKey:
OHCQJHSOBUTRHG-KGGHGJDLSA-N

Cite this record

CBID:2315 http://www.chembase.cn/molecule-2315.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
forskolin
Synonyms
(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(Acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1H-Naphtho[2,1-b]pyran-1-one
(-)-Forskolin
ForsLean
HL 362
L 75-1362B
NSC 357088
7β-Acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one
Coleonol
Colforsin
Forskolin
Forskolin
CAS Number
66428-89-5
64657-11-0
66575-29-9
EC Number
266-410-9
MDL Number
MFCD00082317
Beilstein Number
1692716
PubChem SID
160965767
24894799
46509044
24278035
PubChem CID
47936
CHEBI ID
42471
CHEMBL
52606
Chemspider ID
43607
DrugBank ID
DB02587
Unique Ingredient Identifier
1F7A44V6OU
Wikipedia Title
Forskolin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.565541  H Acceptors
H Donor LogD (pH = 5.5) 1.3561152 
LogD (pH = 7.4) 1.356086  Log P 1.3561156 
Molar Refractivity 104.4681 cm3 Polarizability 42.281574 Å3
Polar Surface Area 113.29 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.28  LOG S -2.57 
Solubility (Water) 1.10e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO: soluble5 mg/mL (stable at least 6 months at room temperature) expand Show data source
ethanol: soluble expand Show data source
Methanol expand Show data source
soluble in organic solvents such as ethanol, chloroform and DMSO expand Show data source
Apperance
off-white powder expand Show data source
White Solid expand Show data source
Melting Point
219-222°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
QL6150000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
21 expand Show data source
Safety Statements
22-36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H312 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
Target
cAMP expand Show data source
Gene Information
human ... OPRK1(4986), SLC2A10(81031), TNF(7124) expand Show data source
Purity
≥98% expand Show data source
≥98% (HPLC) expand Show data source
≥98.0% (TLC) expand Show data source
Grade
for molecular biology expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
from Coleus forskohlii expand Show data source
Product Line
BioReagent expand Show data source
Empirical Formula (Hill Notation)
C22H34O7 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB02587 external link
Item Information
Drug Groups experimental
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]
External Links
Wikipedia
Drugs.com
Sigma Aldrich - F3917 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Analysis Note
Tested for inhibition of interleukin-2 production by Jurkat cells.
Biochem/physiol Actions
Cell-permeable diterpenoid that possesses anti-hypertensive, positive inotropic, and adenylyl cyclase activating properties. Many of its biological effects are due to its activation of adenylyl cyclase and the resulting increase in intracellular cAMP concentration.1 Forskolin effects calcium currents and inhibits MAP kinase.
Sigma Aldrich - F6886 external link
Biochem/physiol Actions
Cell-permeable diterpenoid that possesses anti-hypertensive, positive inotropic, and adenylyl cyclase activating properties. Many of its biological effects are due to its activation of adenylyl cyclase and the resulting increase in intracellular cAMP concentration.1 Forskolin effects calcium currents and inhibits MAP kinase.
Sigma Aldrich - 47735 external link
Biochem/physiol Actions
Cell-permeable diterpenoid that possesses anti-hypertensive, positive inotropic, and adenylyl cyclase activating properties. Many of its biological effects are due to its activation of adenylyl cyclase and the resulting increase in intracellular cAMP concentration.1 Forskolin effects calcium currents and inhibits MAP kinase.
Toronto Research Chemicals - F701800 external link
Forskolin is a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Lindner, E., et al.: Arzneim.-Forsch., 28, 284 (1984)
  • • Hoever, G., et al.: J. Med. Chem., 48, 1256 (1984)
  • • Lai, S., et al.: Eur. J. Clin. Microbiol. Infect. Dis., 24, 5831 (1984)
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PATENTS

PATENTS

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INTERNET

INTERNET

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