CHEBI:5371 - glaucarubinone

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ChEBI Name glaucarubinone
ChEBI ID CHEBI:5371
Definition A quassinoid with formula C25H34O10. It is a natural product isolated from several plant species and exhibits anti-cancer and anti-malarial properties.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H34O10
Net Charge 0
Average Mass 494.537
Monoisotopic Mass 494.21520
InChI InChI=1S/C25H34O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-12,14-18,20,27-28,31-32H,6,8-9H2,1-5H3/t11-,12+,14-,15-,16-,17-,18-,20-,22+,23-,24+,25+/m1/s1
InChIKey WRBGCYVAJRRQKP-STDAJNJZSA-N
SMILES [H][C@]12[C@@]3(O)OC[C@@]11[C@@]([H])(C[C@@]4([H])C(C)=CC(=O)[C@@H](O)[C@]24C)OC(=O)[C@H](OC(=O)[C@@](C)(O)CC)[C@@]1([H])[C@@H](C)[C@H]3O
Metabolite of Species Details
Simarouba amara (NCBI:txid101569) See: PubMed
Ailanthus excelsus (NCBI:txid1133704) Found in bark (BTO:0001301). Isolated form root bark. See: PubMed
Ailanthus excelsus (NCBI:txid1133704) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Ailanthus altissimus (NCBI:txid2768810) Isolated from the samara. See: PubMed
Simarouba glauca (NCBI:txid43729) Found in Root (BTO:0001188). See: PubMed
Nothospondias staudtii (NCBI:txid459131) See: PubMed
Odyendyea gabonensis (NCBI:txid459133) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Simarouba versicolor (NCBI:txid459157) See: PubMed
Simarouba versicolor (NCBI:txid459157) Found in bark (BTO:0001301). Isolated form root bark. 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.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing glaucarubinone (CHEBI:5371) has role antimalarial (CHEBI:38068)
glaucarubinone (CHEBI:5371) has role antineoplastic agent (CHEBI:35610)
glaucarubinone (CHEBI:5371) has role geroprotector (CHEBI:176497)
glaucarubinone (CHEBI:5371) has role plant metabolite (CHEBI:76924)
glaucarubinone (CHEBI:5371) is a carboxylic ester (CHEBI:33308)
glaucarubinone (CHEBI:5371) is a organic heteropentacyclic compound (CHEBI:38164)
glaucarubinone (CHEBI:5371) is a quassinoid (CHEBI:72485)
glaucarubinone (CHEBI:5371) is a secondary α-hydroxy ketone (CHEBI:2468)
glaucarubinone (CHEBI:5371) is a tertiary α-hydroxy ketone (CHEBI:139592)
glaucarubinone (CHEBI:5371) is a tetrol (CHEBI:33573)
IUPAC Name
1β,11α,12α-trihydroxy-2,16-dioxo-11,20-epoxypicras-3-en-15β-yl (2S)-2-hydroxy-2-methylbutanoate
Synonym Source
(+)-glaucarubinone ChEBI
Manual Xrefs Databases
390388 ChemSpider
C00003711 KNApSAcK
C08763 KEGG COMPOUND
View more database links
Registry Number Type Source
1259-86-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
11 October 2021