EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:136429 - usaramine N-oxide

ChEBI IDCHEBI:136429
ChEBI Nameusaramine N-oxide
Stars
ASCII Nameusaramine N-oxide
DefinitionA pyrrolizine alkaloid that is senecionane bearing two additional hydroxy substituents at positions 12 and 18, two additional oxo groups at positions 11 and 16 and an N-oxido substituent.
Last Modified2 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC18H25NO7
Net Charge0
Average Mass367.398
Monoisotopic Mass367.16310
SMILES[H][C@]12C3=CC[N+]1([O-])CC[C@H]2OC(=O)/C(=C/C)C[C@@H](C)[C@](O)(CO)C(=O)OC3
InChIInChI=1S/C18H25NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-,19?/m1/s1
InChIKeyIDIMIWQPUHURPV-BEPQMMTDSA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) MetaboLights (MTBLS429)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
Senecio vulgaris (ncbitaxon:76276) - PubMed (28828276)
Crotalaria pallida (ncbitaxon:3830) - PubMed (28777979)
Roles Classification
Biological Roles:
Jacobaea metabolite  Any plant metabolite that is produced by the genus Jacobaea.
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)
usaramine N-oxide (CHEBI:136429) has functional parent usaramine (CHEBI:9912)
usaramine N-oxide (CHEBI:136429) has role Jacobaea metabolite (CHEBI:139566)
usaramine N-oxide (CHEBI:136429) is a diol (CHEBI:23824)
usaramine N-oxide (CHEBI:136429) is a macrocyclic lactone (CHEBI:63944)
usaramine N-oxide (CHEBI:136429) is a olefinic compound (CHEBI:78840)
usaramine N-oxide (CHEBI:136429) is a organic heterotricyclic compound (CHEBI:26979)
usaramine N-oxide (CHEBI:136429) is a primary alcohol (CHEBI:15734)
usaramine N-oxide (CHEBI:136429) is a pyrrolizine alkaloid (CHEBI:38521)
usaramine N-oxide (CHEBI:136429) is a tertiary alcohol (CHEBI:26878)
usaramine N-oxide (CHEBI:136429) is a tertiary amine oxide (CHEBI:134363)
IUPAC Name 
(3E,5R,6S,14aR,14bR)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-12-oxo-3,4,5,6,11,12,13,14,14a,14b-decahydro-9H-12λ5-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
Synonyms  Source
mucronatine N-oxideChEBI
(15E)-12,18-dihydroxysenecionan-11,16-dione N-oxideChEBI
(15E)-12,18-dihydroxysenecionan-11,16-dione 4-oxideChEBI
Registry NumbersSources
Reaxys:19963004Reaxys
Citations