CHEBI:65954 - gedunin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name gedunin
ChEBI ID CHEBI:65954
Definition A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:67295
Supplier Information
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Formula C28H34O7
Net Charge 0
Average Mass 482.56540
Monoisotopic Mass 482.230
InChI InChI=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
InChIKey YJXDGWUNRYLINJ-BHAPSIHVSA-N
SMILES [H][C@@]12C[C@@H](OC(C)=O)[C@]3(C)[C@]([H])(CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)c3ccoc3)[C@@]1(C)C=CC(=O)C2(C)C
Metabolite of Species Details
Khaya grandifoliola (IPNI:578853-1) Found in seed (BTO:0001226). See: PubMed
Azadirachta indica (NCBI:124943) Found in leaf (BTO:0000713). See: PubMed
Azadirachta indica (NCBI:124943) Found in fruit (BTO:0000486). See: PubMed
Azadirachta indica (NCBI:124943) Found in bark (BTO:0001301). See: PubMed
Cedrela odorata (NCBI:124947) Found in xylem (BTO:0001468). Previous component: wood; See: PubMed
Xylocarpus granatum (NCBI:241841) Found in bark (BTO:0001301). See: PubMed
Cedrela sinensis (NCBI:443222) Found in cortex (PO:0005708). See: PubMed
Azadirachta indica (NCBI:124943) Found in seed (BTO:0001226). Defatted MeOH extract of seeds 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.
Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(−)-gedunin 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
gedunine ChemIDplus
NSC 113497 ChemIDplus
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
Registry Numbers Types Sources
1444894 Reaxys Registry Number Reaxys
2753-30-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10661881 PubMed citation Europe PMC
10820113 PubMed citation Europe PMC
16134059 PubMed citation Europe PMC
16154614 PubMed citation Europe PMC
16989525 PubMed citation Europe PMC
17450509 PubMed citation Europe PMC
18816111 PubMed citation Europe PMC
19551731 PubMed citation Europe PMC
19955938 PubMed citation Europe PMC
19962286 PubMed citation Europe PMC
21381696 PubMed citation Europe PMC
21523424 PubMed citation Europe PMC
21787243 PubMed citation Europe PMC
22709475 PubMed citation Europe PMC
23355466 PubMed citation Europe PMC
9134742 PubMed citation Europe PMC
IND43669361 Agricola citation Europe PMC
Last Modified
09 January 2014