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Structure Database (LMSD)

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Common Name

forskolin

Systematic Name

(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxododecahydro-1H-benzo[f]chromen-5-yl acetate

Synonyms

7beta-acetoxy-8,13-epoxy-1alpha,6beta,9alpha-trihydroxylabd-14-en-11-one
FORSKOLIN
colforsina
colforsine
colforsinum

LM ID

LMPR0104030004

Formula

C₂₂H₃₄O₇

Exact Mass

Calculate m/z

410.230455

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Forskolin is a naturally occurring diterpene that is produced by the Indian Coleus plant (C. forskohlii).¹ It directly activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations.² Forskolin binds to adenylyl cyclase in membranes from stably transfected Sf9 cells expressing type 1 adenylyl cyclase with an IC50 value of 41 nM and demonstrates an EC50 value of 0.5 μM in an activation assay assessing formation of cAMP from ATP.¹ Forskolin also interacts with glucose transporters and certain ion channels and has been used for examining adenylyl cyclase expression, regulation, and G protein signaling.²

This information has been provided by Cayman Chemical

References

1. Robbins, J.D., Boring, D.L., Tang, W.J., et al. Forskolin carbamates: Binding and activation studies with type I adenylyl cyclase. J. Med. Chem. 39(14), 2745-2752 (1996).

2. Insel, P.A., and Ostrom, R.S. Forskolin as a tool for examining adenylyl cyclase expression, regulation, and G protein signaling. Cell Mol. Neurobiol. 23(3), 305-314 (2003).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Plectranthus barbatus (#41228)

Magnoliopsida (#3398)

Structures and stereochemistry of new labdane diterpiniods from coleus forskohlii briq.,
Tetrahedron Letts, 1977

DOI: 10.1016/S0040-4039(01)93245-9

String Representations

InChiKey (Click to copy)

OHCQJHSOBUTRHG-KGGHGJDLSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1C([C@]2([C@]([C@@]3(O)C(=O)C[C@@](C)(O[C@]3(C)[C@H]([C@H]2O)OC(C)=O)C=C)(C)[C@@H](O)C1)[H])(C)C