CHEBI:72669 - (+)-phytocassane D

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ChEBI Name (+)-phytocassane D
ChEBI ID CHEBI:72669
Definition A phytocassane that is (+)-phytocassane A in which the hydroxy group at position 2 has been oxidised to the corresponding ketone, while the keto group at position 3 has been reduced to give the corresponding 3α hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
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/h6,9,11,13,16-18,23H,1,7-8,10H2,2-5H3/t11-,13-,16-,17+,18-,20-/m1/s1
InChIKey DGUIKAVSMBLZCL-MKSLXUROSA-N
SMILES C1C([C@H](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 D (CHEBI:72669) is a diketone (CHEBI:46640)
(+)-phytocassane D (CHEBI:72669) is a phytocassane (CHEBI:139395)
(+)-phytocassane D (CHEBI:72669) is a secondary α-hydroxy ketone (CHEBI:2468)
IUPAC Name
3α-hydroxy-14β-methyl-13-vinyl-5β,8α,9β,10α-podocarp-12-ene-2,11-dione
Synonyms Sources
(2S,4aR,4bR,8S,8aR,10aS)-2-hydroxy-1,1,4a,8-tetramethyl-7-vinyl-1,4a,4b,8,8a,9,10,10a-octahydrophenanthrene-3,5(2H,4H)-dione IUPAC
(2S,4aR,4bR,8S,8aR,10aS)-7-ethenyl-2-hydroxy-1,1,4a,8-tetramethyl-1,4a,4b,8,8a,9,10,10a-octahydrophenanthrene-3,5(2H,4H)-dione IUPAC
(3α,5β,8α,9β,10α,14β)-3-hydroxy-14-methyl-13-vinylpodocarp-12-ene-2,11-dione IUPAC
phytocassane D ChEBI
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).