(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: [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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

JChem

• Acid pKa: 11.565541
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.3561152
• LogD (pH = 7.4): 1.356086
• Log P: 1.3561156
• Molar Refractivity: 104.4681 cm^3
• Polarizability: 42.281574 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.28
• LOG S: -2.57
• Solubility (Water): 1.10e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: soluble5 mg/mL (stable at least 6 months at room temperature); ethanol: soluble; Methanol; soluble in organic solvents such as ethanol, chloroform and DMSO
• Apperance: off-white powder; White Solid
• Melting Point: 219-222°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: QL6150000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 21
• Safety Statements: 22-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H312
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Target: cAMP
• Gene Information: human ... OPRK1(4986), SLC2A10(81031), TNF(7124)

Product Information

• Purity: ≥98%; ≥98% (HPLC); ≥98.0% (TLC)
• Grade: for molecular biology
• Salt Data: Free Base
• Biological Source: from Coleus forskohlii
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C22H34O7

DETAILS

DrugBank - DB02587

• 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

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

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

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

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

• 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)