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CHEBI:65954 - gedunin

Default Structure
ChEBI IDCHEBI:65954
ChEBI Namegedunin
Stars
DefinitionA pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata.
Secondary ChEBI IDCHEBI:67295
Last Modified9 January 2014
DownloadsMolfile
FormulaC28H34O7
Net Charge0
Average Mass482.573
Monoisotopic Mass482.23045
SMILES[H][C@]12CC[C@@]3(C)[C@H](c4ccoc4)OC(=O)[C@H]4O[C@]43[C@]1(C)[C@H](OC(C)=O)C[C@@]1([H])C(C)(C)C(=O)C=C[C@]21C
InChIInChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
InChIKeyYJXDGWUNRYLINJ-BHAPSIHVSA-N
Species of MetaboliteComponentSourceComments
Azadirachta indica (ncbitaxon:124943)
fruit (BTO:0000486) PubMed (9134742)
seed (BTO:0001226) PubMed (21381696) Defatted MeOH extract of seeds
leaf (BTO:0000713) PubMed (9134742)
bark (BTO:0001301) PubMed (9134742)
Cedrela odorata (ncbitaxon:124947) xylem (BTO:0001468) PubMed (9134742) Previous component: wood;
Cedrela sinensis (ncbitaxon:443222) cortex (PO:0005708) PubMed (16989525)
Khaya grandifoliola (IPNI:578853-1) seed (BTO:0001226) PubMed (10661881)
Xylocarpus granatum (ncbitaxon:241841) bark (BTO:0001301) PubMed (17450509)
Roles Classification
Biological Roles:
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.
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
gedunin (CHEBI:65954) has role antimalarial (CHEBI:38068)
gedunin (CHEBI:65954) has role antineoplastic agent (CHEBI:35610)
gedunin (CHEBI:65954) has role Hsp90 inhibitor (CHEBI:63962)
gedunin (CHEBI:65954) has role plant metabolite (CHEBI:76924)
gedunin (CHEBI:65954) is a acetate ester (CHEBI:47622)
gedunin (CHEBI:65954) is a enone (CHEBI:51689)
gedunin (CHEBI:65954) is a epoxide (CHEBI:32955)
gedunin (CHEBI:65954) is a furans (CHEBI:24129)
gedunin (CHEBI:65954) is a lactone (CHEBI:25000)
gedunin (CHEBI:65954) is a limonoid (CHEBI:39434)
gedunin (CHEBI:65954) is a organic heteropentacyclic compound (CHEBI:38164)
gedunin (CHEBI:65954) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming Relation(s)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) has functional parent gedunin (CHEBI:65954)
7-deacetylgedunin (CHEBI:67296) has functional parent gedunin (CHEBI:65954)
IUPAC Name 
(4aR,6R,6aS,6bR,7aS,10R,10aS,12aR,12bR)-10-(3-furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydrooxireno[c]phenanthro[1,2-d]pyran-6-yl acetate
Synonyms  Source
(−)-geduninChEBI
gedunineChemIDplus
NSC 113497ChemIDplus
Oxireno(c)phenanthro(1,2-d)pyran-3,8(3aH,4bH)-dione, 5-(acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyl-,(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-ChEBI
D-homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-(5α,7α,13α,14β,15β,17aα)-ChemIDplus
Registry NumbersSources
Reaxys:1444894Reaxys
CAS:2753-30-2ChemIDplus
Citations