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CHEBI:66326 - 20-hydroxytubocapsanolide A

ChEBI IDCHEBI:66326
ChEBI Name20-hydroxytubocapsanolide A
Stars
DefinitionA withanolide that is the 20-hydroxy derivative of tubocapsanolide A. Isolated from Tubocapsicum anomalum, it exhibits cytotoxic activity.
Last Modified29 October 2019
DownloadsMolfile
FormulaC28H36O7
Net Charge0
Average Mass484.589
Monoisotopic Mass484.24610
SMILES[H][C@@]12C[C@H]3O[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@@](C)(O)[C@@]1([H])CC(C)=C(C)C(=O)O1
InChIInChI=1S/C28H36O7/c1-13-10-20(33-23(31)14(13)2)26(5,32)28-22(35-28)12-17-15-11-21-27(34-21)19(30)7-6-18(29)25(27,4)16(15)8-9-24(17,28)3/h6-7,15-17,19-22,30,32H,8-12H2,1-5H3/t15-,16+,17+,19+,20-,21-,22-,24+,25+,26+,27-,28-/m1/s1
InChIKeyONOYEGAYNUISOH-QTRSZHGFSA-N
Species of MetaboliteComponentSourceComments
Tubocapsicum anomalum (ncbitaxon:180580) - PubMed (17417907)
Roles Classification
Biological Role:
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)
20-hydroxytubocapsanolide A (CHEBI:66326) has functional parent tubocapsanolide A (CHEBI:66325)
20-hydroxytubocapsanolide A (CHEBI:66326) has role antineoplastic agent (CHEBI:35610)
20-hydroxytubocapsanolide A (CHEBI:66326) is a 20-hydroxy steroid (CHEBI:36854)
20-hydroxytubocapsanolide A (CHEBI:66326) is a 4-hydroxy steroid (CHEBI:62846)
20-hydroxytubocapsanolide A (CHEBI:66326) is a enone (CHEBI:51689)
20-hydroxytubocapsanolide A (CHEBI:66326) is a epoxy steroid (CHEBI:145217)
20-hydroxytubocapsanolide A (CHEBI:66326) is a ergostanoid (CHEBI:50403)
20-hydroxytubocapsanolide A (CHEBI:66326) is a secondary alcohol (CHEBI:35681)
20-hydroxytubocapsanolide A (CHEBI:66326) is a tertiary alcohol (CHEBI:26878)
20-hydroxytubocapsanolide A (CHEBI:66326) is a withanolide (CHEBI:74716)
20-hydroxytubocapsanolide A (CHEBI:66326) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4β,5β,6β,16α,17α)-17-{(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl}-4-hydroxy-5,6:16,17-diepoxyandrost-2-en-1-one
Synonym  Source
5β,6β:16α,17α-diepoxy-4β,20-dihydroxy-1-oxo-witha-2,24-dienolideChEBI
Registry NumbersSources
Reaxys:11130281Reaxys
Citations