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CHEBI:67302 - 23-epivepaol

ChEBI IDCHEBI:67302
ChEBI Name23-epivepaol
Stars
DefinitionA limonoid that is the C-23 epimer of vepaol. It has been isolated from Azadirachta indica.
Last Modified3 March 2015
DownloadsMolfile
FormulaC36H48O17
Net Charge0
Average Mass752.763
Monoisotopic Mass752.28915
SMILES[H][C@@]12O[C@@H](OC)C[C@]1(O)[C@]1([H])C[C@]([H])(O2)[C@@]2([C@]3(C)[C@H](O)[C@]4([H])OC[C@]5(C(=O)OC)[C@H](OC(C)=O)C[C@H](OC(=O)/C(C)=C/C)[C@@]6(CO[C@](O)(C(=O)OC)[C@@]36[H])[C@@]45[H])O[C@@]12C
InChIInChI=1S/C36H48O17/c1-9-15(2)25(39)50-18-11-19(49-16(3)37)33(27(40)45-7)13-47-22-23(33)32(18)14-48-35(43,28(41)46-8)26(32)30(4,24(22)38)36-20-10-17(31(36,5)53-36)34(42)12-21(44-6)52-29(34)51-20/h9,17-24,26,29,38,42-43H,10-14H2,1-8H3/b15-9+/t17-,18+,19-,20+,21-,22-,23-,24-,26+,29-,30-,31+,32+,33+,34+,35+,36+/m1/s1
InChIKeyHAIAPLNAMFKNPR-QYMXIDFGSA-N
Species of MetaboliteComponentSourceComments
Azadirachta indica (ncbitaxon:124943) seed (BTO:0001226) PubMed (21381696) Defatted MeOH extract of seeds
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
23-epivepaol (CHEBI:67302) has functional parent tiglic acid (CHEBI:9592)
23-epivepaol (CHEBI:67302) has role metabolite (CHEBI:25212)
23-epivepaol (CHEBI:67302) has role plant metabolite (CHEBI:76924)
23-epivepaol (CHEBI:67302) is a acetate ester (CHEBI:47622)
23-epivepaol (CHEBI:67302) is a epoxide (CHEBI:32955)
23-epivepaol (CHEBI:67302) is a limonoid (CHEBI:39434)
23-epivepaol (CHEBI:67302) is a methyl ester (CHEBI:25248)
23-epivepaol (CHEBI:67302) is a secondary alcohol (CHEBI:35681)
23-epivepaol (CHEBI:67302) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(acetyloxy)-3,5-dihydroxy-4-[(1aR,2S,3aR,5R,6aS,7S,7aS)-6a-hydroxy-5-methoxy-7a-methylhexahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8H)-dicarboxylate
Synonym  Source
IsovepaolChEBI
Registry NumbersSources
Reaxys:11303121Reaxys
Citations