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CHEBI:72669 - (+)-phytocassane D

Default Structure
ChEBI IDCHEBI:72669
ChEBI Name(+)-phytocassane D
Stars
DefinitionA 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.
Last Modified6 February 2018
SubmitterSteve
DownloadsMolfile
FormulaC20H28O3
Net Charge0
Average Mass316.441
Monoisotopic Mass316.20384
SMILES[H][C@@]12C(=O)C=C(C=C)[C@@H](C)[C@@]1([H])CC[C@]1([H])C(C)(C)[C@H](O)C(=O)C[C@@]21C
InChIInChI=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
InChIKeyDGUIKAVSMBLZCL-MKSLXUROSA-N
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
phytoalexin  A toxin made by a plant that acts against an organism attacking it.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(+)-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  Source
(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)-dioneIUPAC
(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)-dioneIUPAC
(3α,5β,8α,9β,10α,14β)-3-hydroxy-14-methyl-13-vinylpodocarp-12-ene-2,11-dioneIUPAC
phytocassane DChEBI