CHEBI:66328 - tubocapsanolide F

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ChEBI Name tubocapsanolide F
ChEBI ID CHEBI:66328
Definition A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 17 (the 4β,5β,6β,22R stereoisomer). 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 C28H38O6
Net Charge 0
Average Mass 470.59770
Monoisotopic Mass 470.26684
InChI InChI=1S/C28H38O6/c1-14-12-20(33-24(31)15(14)2)16(3)27(32)11-9-18-17-13-23-28(34-23)22(30)7-6-21(29)26(28,5)19(17)8-10-25(18,27)4/h6-7,16-20,22-23,30,32H,8-13H2,1-5H3/t16-,17+,18+,19+,20-,22+,23-,25+,26+,27+,28-/m1/s1
InChIKey FBVUDUMNPFUQRB-PCLPIYRRSA-N
SMILES [H][C@@]1(CC(C)=C(C)C(=O)O1)[C@@H](C)[C@@]1(O)CC[C@@]2([H])[C@]3([H])C[C@@]4([H])O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C
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 tubocapsanolide F (CHEBI:66328) has role antineoplastic agent (CHEBI:35610)
tubocapsanolide F (CHEBI:66328) is a δ-lactone (CHEBI:18946)
tubocapsanolide F (CHEBI:66328) is a 17α-hydroxy steroid (CHEBI:35342)
tubocapsanolide F (CHEBI:66328) is a 4-hydroxy steroid (CHEBI:62846)
tubocapsanolide F (CHEBI:66328) is a enone (CHEBI:51689)
tubocapsanolide F (CHEBI:66328) is a epoxy steroid (CHEBI:145217)
tubocapsanolide F (CHEBI:66328) is a ergostanoid (CHEBI:50403)
tubocapsanolide F (CHEBI:66328) is a secondary alcohol (CHEBI:35681)
tubocapsanolide F (CHEBI:66328) is a tertiary alcohol (CHEBI:26878)
tubocapsanolide F (CHEBI:66328) is a withanolide (CHEBI:74716)
IUPAC Name
(4β,5β,6β,22R)-4,17-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Synonyms Sources
17-hydroxy-27-deoxywithaferin A ChEBI
5β,6β-epoxy-4β,17α-dihydroxy-1-oxo-witha-2,24-dienolide ChEBI
Registry Number Type Source
11130284 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17417907 PubMed citation Europe PMC
Last Modified
28 October 2019