CHEBI:66325 - tubocapsanolide A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name tubocapsanolide A
ChEBI ID CHEBI:66325
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C28H36O6
Net Charge 0
Average Mass 468.58180
Monoisotopic Mass 468.25119
InChI InChI=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
InChIKey RQGXOMVMGPVOQK-KAUDDYPASA-N
SMILES [H][C@@]1(CC(C)=C(C)C(=O)O1)[C@@H](C)[C@@]12O[C@]1([H])C[C@@]1([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@]21C
Metabolite of Species Details
Tubocapsicum anomalum (NCBI:txid180580) See: PubMed
Roles Classification
Biological Role(s): NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-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.
(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 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 δ-lactone (CHEBI:18946)
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)
Incoming 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-dienolide ChEBI
Registry Number Type Source
11130280 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17417907 PubMed citation Europe PMC
17513606 PubMed citation Europe PMC
19049961 PubMed citation Europe PMC
Last Modified
28 October 2019