Structure Database (LMSD)

Common Name
1,9-dideoxyforskolin
Systematic Name
(3R,4aS,5S,6S,6aS,10aS,10bR)-3-ethenyl-6-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxododecahydro-1H-benzo[f]chromen-5-yl acetate
Synonyms
  • (3R,4aS,5S,6S,6aS,10aS,10bR)-5-(acetyloxy)-3-ethenyldodecahydro-6-hydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran-1-one
  • (3R-(3alpha,4abeta,5beta,6beta,6aalpha,10abeta,10balpha))-5-(acetyloxy)-3-ethenyldodecahydro-6-hydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran-1-one
  • 7beta-acetoxy-8,13-epoxy-6beta-hydroxylabd-14-en-11-one
LM ID
LMPR0104030009
Formula
C22H34O5
Exact Mass
Calculate m/z
378.240626
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C20 isoprenoids (diterpenes) [PR0104]
Labdane and halimane diterpenoids [PR010403]

Biological Context

1,9-dideoxy Forskolin is an analog of forskolin that interacts with, but does not activate, adenylyl cyclase.1,2

This information has been provided by Cayman Chemical

References

1. McHugh, E.M., and McGee, R., Jr. Direct anesthetic-like effects of forskolin on the nicotinic acetylcholine receptors of PC12 cells. The Journal of Biological Chemisty 261(7), 3103-3106 (1986).
1. McHugh, E.M., and McGee, R., Jr. Direct anesthetic-like effects of forskolin on the nicotinic acetylcholine receptors of PC12 cells. The Journal of Biological Chemisty 261(7), 3103-3106 (1986).
2. Pinto, C., Hübner, M., Gille, A., et al. Differential interactions of the catalytic subunits of adenylyl cyclase with forskolin analogs. Biochem. Pharmacol. 78(1), 62-69 (2009).
2. Pinto, C., Hübner, M., Gille, A., et al. Differential interactions of the catalytic subunits of adenylyl cyclase with forskolin analogs. Biochem. Pharmacol. 78(1), 62-69 (2009).

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

String Representations

InChiKey (Click to copy)
ZKZMDXUDDJYAIB-SUCLLAFCSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1C([C@]2([C@]([C@@]3([H])C(=O)C[C@@](C)(O[C@]3(C)[C@H]([C@H]2O)OC(C)=O)C=C)(C)CC1)[H])(C)C

Other Databases

CHEBI ID
50295
PubChem CID
107948
Cayman ID
11664
GuidePharm ID
4100

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 3
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 388.11
Topological Polar Surface Area 74.90
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 4.58
Molar Refractivity 104.04

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