CHEBI:72664 - (+)-phytocassane A

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ChEBI Name (+)-phytocassane A
ChEBI ID CHEBI:72664
Definition A phytocassane that is ent-podocarp-12-ene-3,11-dione carrying additional hydroxy, vinyl and methyl substituents at the 2α, 13 and 14 positions, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H28O3
Net Charge 0
Average Mass 316.435
Monoisotopic Mass 316.20384
InChI InChI=1S/C20H28O3/c1-6-12-9-14(21)17-13(11(12)2)7-8-16-19(3,4)18(23)15(22)10-20(16,17)5/h6,9,11,13,15-17,22H,1,7-8,10H2,2-5H3/t11-,13-,15-,16-,17+,20-/m1/s1
InChIKey XVEOIKIXOSKAFL-BJASISCMSA-N
SMILES C1[C@H](C(C([C@]2([H])[C@]1(C)[C@@]3(C(C=C([C@H]([C@]3(CC2)[H])C)C=C)=O)[H])(C)C)=O)O
Roles Classification
Biological Role(s): phytoalexin
A toxin made by a plant that acts against an organism attacking it.
(via phytocassane )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via phytocassane )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via phytocassane )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (+)-phytocassane A (CHEBI:72664) is a diketone (CHEBI:46640)
(+)-phytocassane A (CHEBI:72664) is a phytocassane (CHEBI:139395)
(+)-phytocassane A (CHEBI:72664) is a secondary α-hydroxy ketone (CHEBI:2468)
IUPAC Name
2α-hydroxy-14β-methyl-13-vinyl-5β,8α,9β,10α-podocarp-12-ene-3,11-dione
Synonyms Sources
(2α,5β,8α,9β,10α,14β)-2-hydroxy-14-methyl-13-vinylpodocarp-12-ene-3,11-dione IUPAC
(3R,4aR,4bR,8S,8aR,10aS)-3-hydroxy-1,1,4a,8-tetramethyl-7-vinyl-1,3,4,4a,4b,8,8a,9,10,10a-decahydrophenanthrene-2,5-dione IUPAC
ent-2β-hydroxy-12,15-cassadiene-3,11-dione ChEBI
phytocassane A ChEBI
Manual Xref Database
CPD-7094 MetaCyc
View more database links
Registry Number Type Source
8509348 Reaxys Registry Number Reaxys
Last Modified
06 February 2018
General Comment
2018-01-11 The phytocassanes were originally proposed as cassane diterpenoids. It was later shown that their stereochemistry is that of ent-cassane (Tetrahedron Lett., 2000, v1, pp. 351-354).