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CHEBI:66122 - jerantinine D

Default Structure
ChEBI IDCHEBI:66122
ChEBI Namejerantinine D
Stars
DefinitionAn indole alkaloid that is jerantinine C substituted by an epoxy group across positions 14 and 15. Isolated from Tabernaemontana corymbosa, it exhibits cytotoxicity against human KB cells.
Last Modified30 March 2015
DownloadsMolfile
FormulaC22H24N2O6
Net Charge0
Average Mass412.442
Monoisotopic Mass412.16344
SMILES[H][C@]12O[C@@]1([H])C(=O)N1CC[C@]34C(=C(C(=O)OC)C[C@@]2(CC)[C@]13[H])Nc1cc(OC)c(O)cc14
InChIInChI=1S/C22H24N2O6/c1-4-21-9-10(19(27)29-3)16-22(11-7-13(25)14(28-2)8-12(11)23-16)5-6-24(20(21)22)18(26)15-17(21)30-15/h7-8,15,17,20,23,25H,4-6,9H2,1-3H3/t15-,17+,20+,21-,22+/m1/s1
InChIKeyNCDJGOXCXAXUIG-PVUPTQESSA-N
Species of MetaboliteComponentSourceComments
Tabernaemontana corymbosa (IPNI:82070-1) leaf (BTO:0000713) PubMed (18778099)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
jerantinine D (CHEBI:66122) has functional parent jerantinine C (CHEBI:66121)
jerantinine D (CHEBI:66122) has role antineoplastic agent (CHEBI:35610)
jerantinine D (CHEBI:66122) has role metabolite (CHEBI:25212)
jerantinine D (CHEBI:66122) is a alkaloid ester (CHEBI:38481)
jerantinine D (CHEBI:66122) is a aromatic ether (CHEBI:35618)
jerantinine D (CHEBI:66122) is a epoxide (CHEBI:32955)
jerantinine D (CHEBI:66122) is a indole alkaloid (CHEBI:38958)
jerantinine D (CHEBI:66122) is a lactam (CHEBI:24995)
jerantinine D (CHEBI:66122) is a methyl ester (CHEBI:25248)
jerantinine D (CHEBI:66122) is a organic heterohexacyclic compound (CHEBI:51914)
jerantinine D (CHEBI:66122) is a phenols (CHEBI:33853)
IUPAC Name 
methyl (5α,6α,7α,12β,19α)-15-hydroxy-16-methoxy-8-oxo-2,3-didehydro-6,7-epoxyaspidospermidine-3-carboxylate
Registry NumbersSources
Reaxys:19172526Reaxys
Citations