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CHEBI:132352 - triptoquinone A

ChEBI IDCHEBI:132352
ChEBI Nametriptoquinone A
Stars
DefinitionA tricyclic diterpenoid with formula C20H24O4, originally isolated from Tripterygium wilfordii.
Last Modified24 October 2016
Submitterliuqingping
DownloadsMolfile
FormulaC20H24O4
Net Charge0
Average Mass328.408
Monoisotopic Mass328.16746
SMILES[H][C@@]12CCC3=C(C(=O)C=C(C(C)C)C3=O)[C@@]1(C)CCC(C(=O)O)=C2C
InChIInChI=1S/C20H24O4/c1-10(2)14-9-16(21)17-13(18(14)22)5-6-15-11(3)12(19(23)24)7-8-20(15,17)4/h9-10,15H,5-8H2,1-4H3,(H,23,24)/t15-,20-/m0/s1
InChIKeyPDPFWAJAYGLYHD-YWZLYKJASA-N
Species of MetaboliteComponentSourceComments
Tripterygium wilfordii (ncbitaxon:458696) - PubMed (8699928)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
ChEBI Ontology
Outgoing Relation(s)
triptoquinone A (CHEBI:132352) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
triptoquinone A (CHEBI:132352) has role plant metabolite (CHEBI:76924)
triptoquinone A (CHEBI:132352) is a p-quinones (CHEBI:25830)
triptoquinone A (CHEBI:132352) is a abietane diterpenoid (CHEBI:36762)
triptoquinone A (CHEBI:132352) is a carbotricyclic compound (CHEBI:38032)
triptoquinone A (CHEBI:132352) is a cyclic terpene ketone (CHEBI:36130)
triptoquinone A (CHEBI:132352) is a tricyclic diterpenoid (CHEBI:79084)
triptoquinone A (CHEBI:132352) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(4aS,10aS)-1,4a-dimethyl-5,8-dioxo-7-(propan-2-yl)-3,4,4a,5,8,9,10,10a-octahydrophenanthrene-2-carboxylic acid
Synonym  Source
(4aS-trans)-3,4,4a,5,8,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylic acidChemIDplus
Manual XrefsDatabases
132524PubChem Compound
C00035774KNApSAcK
Registry NumbersSources
Reaxys:5450180Reaxys
CAS:142950-86-5KNApSAcK
CAS:142950-86-5ChemIDplus
Citations