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CHEBI:65954 - gedunin
| Formula | C28H34O7 |
| Net Charge | 0 |
| Average Mass | 482.573 |
| Monoisotopic Mass | 482.23045 |
| 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 |
| 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 |
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Azadirachta indica (ncbitaxon:124943) | |||
| fruit (BTO:0000486) | PubMed (9134742) | ||
| leaf (BTO:0000713) | PubMed (9134742) | ||
| bark (BTO:0001301) | PubMed (9134742) | ||
| seed (BTO:0001226) | PubMed (21381696) | Defatted MeOH extract of seeds | |
| Cedrela sinensis (ncbitaxon:443222) | cortex (PO:0005708) | PubMed (16989525) | |
| Xylocarpus granatum (ncbitaxon:241841) | bark (BTO:0001301) | PubMed (17450509) | |
| Cedrela odorata (ncbitaxon:124947) | xylem (BTO:0001468) | PubMed (9134742) | Previous component: wood; |
| Khaya grandifoliola (IPNI:578853-1) | seed (BTO:0001226) | PubMed (10661881) |
| 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. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. Hsp90 inhibitor An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90. |
| 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 |
|---|---|
| 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 |
| (−)-gedunin | ChEBI |
| gedunine | ChemIDplus |
| NSC 113497 | ChemIDplus |
| Registry Numbers | Sources |
|---|---|
| Reaxys:1444894 | Reaxys |
| CAS:2753-30-2 | ChemIDplus |
| Citations |
|---|