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CHEBI:66325 - tubocapsanolide A

ChEBI IDCHEBI:66325
ChEBI Nametubocapsanolide A
Stars
DefinitionA withanolide that is 5β,6β:16α,17α-diepoxywitha-2,24-dienolide substituted by a hydroxy group at position 4 and an oxo group at position 1. Isolated from Tubocapsicum anomalum, it exhibits cytotoxic activity.
Last Modified28 October 2019
DownloadsMolfile
FormulaC28H36O6
Net Charge0
Average Mass468.590
Monoisotopic Mass468.25119
SMILES[H][C@@]12C[C@@]3([H])O[C@]34[C@@H](O)C=CC(=O)[C@]4(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])C[C@@]2([H])O[C@@]12[C@H](C)[C@@]1([H])CC(C)=C(C)C(=O)O1
InChIInChI=1S/C28H36O6/c1-13-10-19(32-24(31)14(13)2)15(3)27-23(33-27)12-18-16-11-22-28(34-22)21(30)7-6-20(29)26(28,5)17(16)8-9-25(18,27)4/h6-7,15-19,21-23,30H,8-12H2,1-5H3/t15-,16-,17+,18+,19-,21+,22-,23-,25+,26+,27-,28-/m1/s1
InChIKeyRQGXOMVMGPVOQK-KAUDDYPASA-N
Species of MetaboliteComponentSourceComments
Tubocapsicum anomalum (ncbitaxon:180580) - PubMed (17417907)
Roles Classification
Biological Roles:
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
tubocapsanolide A (CHEBI:66325) has role antineoplastic agent (CHEBI:35610)
tubocapsanolide A (CHEBI:66325) has role NF-κB inhibitor (CHEBI:73240)
tubocapsanolide A (CHEBI:66325) is a 4-hydroxy steroid (CHEBI:62846)
tubocapsanolide A (CHEBI:66325) is a enone (CHEBI:51689)
tubocapsanolide A (CHEBI:66325) is a epoxy steroid (CHEBI:145217)
tubocapsanolide A (CHEBI:66325) is a ergostanoid (CHEBI:50403)
tubocapsanolide A (CHEBI:66325) is a secondary alcohol (CHEBI:35681)
tubocapsanolide A (CHEBI:66325) is a withanolide (CHEBI:74716)
tubocapsanolide A (CHEBI:66325) is a δ-lactone (CHEBI:18946)
Incoming Relation(s)
20-hydroxytubocapsanolide A (CHEBI:66326) has functional parent tubocapsanolide A (CHEBI:66325)
23-hydroxytubocapsanolide A (CHEBI:66327) has functional parent tubocapsanolide A (CHEBI:66325)
IUPAC Name 
(4β,5β,6β,16α,17α)-17-{(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-4-hydroxy-5,6:16,17-diepoxyandrost-2-en-1-one
Synonym  Source
5β,6β:16α,17α-diepoxy-4β-hydroxy-1-oxo-witha-2,24-dienolideChEBI
Registry NumbersSources
Reaxys:11130280Reaxys
Citations