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CHEBI:66327 - 23-hydroxytubocapsanolide A

ChEBI IDCHEBI:66327
ChEBI Name23-hydroxytubocapsanolide A
Stars
DefinitionA withanolide that is the 23-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@@]1([C@@H](C)[C@@]23O[C@]2([H])C[C@@]2([H])[C@]4([H])C[C@H]5O[C@]56[C@@H](O)C=CC(=O)[C@]6(C)[C@@]4([H])CC[C@@]23C)OC(=O)C(C)=C(C)[C@@H]1O
InChIInChI=1S/C28H36O7/c1-12-13(2)24(32)33-23(22(12)31)14(3)27-21(34-27)11-17-15-10-20-28(35-20)19(30)7-6-18(29)26(28,5)16(15)8-9-25(17,27)4/h6-7,14-17,19-23,30-31H,8-11H2,1-5H3/t14-,15-,16+,17+,19+,20-,21-,22+,23+,25+,26+,27-,28-/m1/s1
InChIKeyZTDAKBMARSMGBP-FVMAOMGMSA-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)
23-hydroxytubocapsanolide A (CHEBI:66327) has functional parent tubocapsanolide A (CHEBI:66325)
23-hydroxytubocapsanolide A (CHEBI:66327) has role antineoplastic agent (CHEBI:35610)
23-hydroxytubocapsanolide A (CHEBI:66327) is a 23-hydroxy steroid (CHEBI:36866)
23-hydroxytubocapsanolide A (CHEBI:66327) is a 4-hydroxy steroid (CHEBI:62846)
23-hydroxytubocapsanolide A (CHEBI:66327) is a enone (CHEBI:51689)
23-hydroxytubocapsanolide A (CHEBI:66327) is a epoxy steroid (CHEBI:145217)
23-hydroxytubocapsanolide A (CHEBI:66327) is a ergostanoid (CHEBI:50403)
23-hydroxytubocapsanolide A (CHEBI:66327) is a secondary alcohol (CHEBI:35681)
23-hydroxytubocapsanolide A (CHEBI:66327) is a withanolide (CHEBI:74716)
23-hydroxytubocapsanolide A (CHEBI:66327) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4β,5β,6β,16α,17α)-4-hydroxy-17-{(1R)-1-[(2S,3S)-3-hydroxy-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-5,6:16,17-diepoxyandrost-2-en-1-one
Synonym  Source
5β,6β:16α,17α-diepoxy-4β,23-dihydroxy-1-oxo-witha-2,24-dienolideChEBI
Registry NumbersSources
Reaxys:11130282Reaxys
Citations