CHEBI:66326 - 20-hydroxytubocapsanolide A

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ChEBI Name 20-hydroxytubocapsanolide A
ChEBI ID CHEBI:66326
Definition A withanolide that is the 20-hydroxy derivative of tubocapsanolide A. Isolated from Tubocapsicum anomalum, it exhibits cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H36O7
Net Charge 0
Average Mass 484.58120
Monoisotopic Mass 484.24610
InChI InChI=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
InChIKey ONOYEGAYNUISOH-QTRSZHGFSA-N
SMILES CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@@]12O[C@@H]1C[C@H]1[C@@H]3C[C@H]4O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]21C
Metabolite of Species Details
Tubocapsicum anomalum (NCBI:txid180580) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via withanolide )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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)
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-dienolide ChEBI
Registry Number Type Source
11130281 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17417907 PubMed citation Europe PMC
Last Modified
29 October 2019