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gedunin (CHEBI:65954)

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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
See structure as:  Image  Applet
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Formula Source
C28H34O7 ChEBI
Net Charge 0
Average Mass 482.56540
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 Sources
Isolated from Khaya grandifoliola (IPNI:578853-1) found in seed (BTO:0001226) PubMed
Isolated from Azadirachta indica (NCBI:124943) found in leaf (BTO:0000713) PubMed
Isolated from Azadirachta indica (NCBI:124943) found in fruit (BTO:0000486 ) PubMed
Isolated from Azadirachta indica (NCBI:124943) found in bark (BTO:0001301 ) PubMed
Isolated from Cedrela odorata (NCBI:124947) found in wood (BTO:0001468) PubMed
Isolated from Xylocarpus granatum (NCBI:241841) found in bark (BTO:0001301) PubMed
Isolated from Cedrela sinensis (NCBI:443222) found in cortex (PO:0005708) PubMed
Isolated from Azadirachta indica (NCBI:124943) found in seed (BTO:0001226) PubMed
Roles Classification
Chemical Role(s): Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Biological Role(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.
Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
plant secondary metabolite
Any plant metabolite that is not directly involved in the normal growth, development or reproduction of plants.
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 on the 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 secondary metabolite (CHEBI:75766)
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 CiteXplore
10820113 PubMed citation CiteXplore
16134059 PubMed citation CiteXplore
16154614 PubMed citation CiteXplore
16989525 PubMed citation CiteXplore
17450509 PubMed citation CiteXplore
18816111 PubMed citation CiteXplore
19551731 PubMed citation CiteXplore
19955938 PubMed citation CiteXplore
19962286 PubMed citation CiteXplore
21381696 PubMed citation CiteXplore
21523424 PubMed citation CiteXplore
21787243 PubMed citation CiteXplore
22709475 PubMed citation CiteXplore
23355466 PubMed citation CiteXplore
9134742 PubMed citation CiteXplore
IND43669361 Agricola citation CiteXplore
Last Modified
09 January 2014

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