Forskolin (CHEM003783)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (17)XML
Record Information
Version1.0
Creation Date2014-09-11 05:18:11 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003783
Identification
Common NameForskolin
ClassSmall Molecule
DescriptionPotent 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.
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7beta-Acetoxy-8,13-epoxy-1alpha,6beta,9alpha-trihydroxylabd-14-en-11-oneChEBI
ColeonolChEBI
ColeonolkChEBI
ColforsinaChEBI
ColforsineChEBI
ColforsinumChEBI
ForskolinKegg
7b-Acetoxy-8,13-epoxy-1a,6b,9a-trihydroxylabd-14-en-11-oneGenerator
7Β-acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-oneGenerator
ColforsinChEBI
N,N-Dimethyl-beta-alanine-5-(acetyloxy)-3-ethenyldodecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho(2,1-b)pyran-6-yl ester HCLMeSH
NKH 477MeSH
NKH-477MeSH
Chemical FormulaC22H34O7
Average Molecular Mass410.501 g/mol
Monoisotopic Mass410.230 g/mol
CAS Registry Number64657-11-0 and 66575-29-9
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
Traditional Nameforskolin
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
InChI IdentifierInChI=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
InChI KeyOHCQJHSOBUTRHG-KGGHGJDLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Naphthopyran
  • Naphthalene
  • Pyran
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.1 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 Area113.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.47 m³·mol⁻¹ChemAxon
Polarizability43.33 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0001900000-7d8f5636999f6b276cd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0k92-0349200000-7e9f95896c6366092dc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zgi-0895000000-d5ffd6e415b7071865cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0941000000-0d4b697cc719902e9cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1009200000-20fab1621372984846a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxu-2009000000-f130396db84635f9cd93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-9101000000-237fd86ca77bf89a6101Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3009600000-51bddbda26cd550ea75aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-6139100000-fb3680fca9d4a76753d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-894a6ba44b323c93d1b5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02587
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003416
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkForskolin
Chemspider IDNot Available
ChEBI ID42471
PubChem Compound ID47936
Kegg Compound IDC09076
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

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

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11816015
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12676767
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12836714
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14691682
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15135319
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15380183
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=1547891
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15525467
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16644480
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17570033
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19831022
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7755573
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=7875530
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=7898427
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=7929167
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=8489512
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=8985363
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=9478958
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=9828101