CHEBI:65907 - forskoditerpenoside C

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ChEBI Name forskoditerpenoside C
ChEBI ID CHEBI:65907
Definition A diterpene glycoside that is labd-14-en-11-one substituted by β-acetoxy group at position 6, an epoxy group between positions 8 and 13, a β-hydroxy group at position 7 and a β-D-glucopyranosyloxy group at position 1 (the 1α stereoisomer). Isolated from the whole plant of Coleus forskohlii, it shows relaxative effects on isolated guinea pig tracheal spirals in vitro.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H44O11
Net Charge 0
Average Mass 556.64240
Monoisotopic Mass 556.28836
InChI InChI=1S/C28H44O11/c1-8-26(5)11-14(31)21-27(6)16(38-24-19(34)18(33)17(32)15(12-29)37-24)9-10-25(3,4)22(27)20(36-13(2)30)23(35)28(21,7)39-26/h8,15-24,29,32-35H,1,9-12H2,2-7H3/t15-,16+,17-,18+,19-,20+,21-,22+,23+,24+,26+,27-,28+/m1/s1
InChIKey JLNFSODBKULJEE-NEXFZGQFSA-N
SMILES [H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O[C@H]1CCC(C)(C)[C@]2([H])[C@H](OC(C)=O)[C@H](O)[C@@]3(C)O[C@](C)(CC(=O)[C@]3([H])[C@@]12C)C=C
Metabolite of Species Details
Coleus forskohlii (NCBI:txid41228) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing forskoditerpenoside C (CHEBI:65907) has role metabolite (CHEBI:25212)
forskoditerpenoside C (CHEBI:65907) has role muscle relaxant (CHEBI:51371)
forskoditerpenoside C (CHEBI:65907) is a β-D-glucoside (CHEBI:22798)
forskoditerpenoside C (CHEBI:65907) is a acetate ester (CHEBI:47622)
forskoditerpenoside C (CHEBI:65907) is a cyclic ether (CHEBI:37407)
forskoditerpenoside C (CHEBI:65907) is a cyclic ketone (CHEBI:3992)
forskoditerpenoside C (CHEBI:65907) is a diterpene glycoside (CHEBI:71939)
forskoditerpenoside C (CHEBI:65907) is a labdane diterpenoid (CHEBI:36770)
IUPAC Name
(3R,4aS,5S,6S,6aS,10S,10aS,10bR)-10-(β-D-glucopyranosyloxy)-5-hydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyldodecahydro-1H-benzo[f]chromen-6-yl acetate
Synonym Source
6β-acetoxy-7β-hydroxy-8,13-epoxy-labd-14-en-11-one-1α-O-β-D-glucopyranoside ChEBI
Registry Number Type Source
15762063 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18175974 PubMed citation Europe PMC
Last Modified
25 January 2013