CHEBI:65617 - 2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane

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ChEBI Name 2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane
ChEBI ID CHEBI:65617
ChEBI ASCII Name 2alpha-(2'-pyrrolyl)-4alpha-methoxycarbonyl-5beta-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane
Definition An oxazinane alkaloid that is methyl (4S)-1,3-oxazinane-4-carboxylate substituted by a (1H-pyrrol-2-yl group at position 2 and a 2-methylheptyl group at position 5. Isolated from Celastrus angulatus, it exhibits cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H30N2O3
Net Charge 0
Average Mass 322.44240
Monoisotopic Mass 322.22564
InChI InChI=1S/C18H30N2O3/c1-4-5-6-8-13(2)11-14-12-23-17(15-9-7-10-19-15)20-16(14)18(21)22-3/h7,9-10,13-14,16-17,19-20H,4-6,8,11-12H2,1-3H3/t13?,14-,16-,17+/m0/s1
InChIKey UNQFHHAPQIDJED-AZZBFNOKSA-N
SMILES CCCCCC(C)C[C@H]1CO[C@@H](N[C@@H]1C(=O)OC)c1ccc[nH]1
Metabolite of Species Details
Celastrus angulatus (NCBI:txid489977) Found in seed (BTO:0001226). See: DOI
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane (CHEBI:65617) has role antineoplastic agent (CHEBI:35610)
2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane (CHEBI:65617) has role metabolite (CHEBI:25212)
2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane (CHEBI:65617) is a alkaloid (CHEBI:22315)
2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane (CHEBI:65617) is a methyl ester (CHEBI:25248)
2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane (CHEBI:65617) is a oxazinane (CHEBI:46952)
2α-(2'-pyrrolyl)-4α-methoxycarbonyl-5β-[(2''-methyl)-heptyl]-1,3-oxazacyclohexane (CHEBI:65617) is a pyrroles (CHEBI:26455)
IUPAC Name
methyl (2R,4S,5R)-5-(2-methylheptyl)-2-(1H-pyrrol-2-yl)-1,3-oxazinane-4-carboxylatemethyl (2R,4S,5R)-5-(2-methylheptyl)-2-(1H-pyrrol-2-yl)-1,3-oxazinane-4-carboxylate
Synonyms Sources
4α-methoxycarbonyl-5β-(2''-methylheptyl)-2α-(2'-pyrrolyl)-3,4,5,6-tetrahydro-1,3,2H-oxazine ChEBI
chinese bittersweet alkaloid II ChEBI
Registry Number Type Source
8503882 Reaxys Registry Number Reaxys
Last Modified
03 March 2015
General Comment
2013-07-30 Phytochemistry (1999), 52, 1731-1734