CHEBI:28012 - lupinine

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ChEBI Name lupinine
ChEBI ID CHEBI:28012
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6573, CHEBI:25084
Supplier Information
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Formula C10H19NO
Net Charge 0
Average Mass 169.26400
Monoisotopic Mass 169.147
InChI InChI=1S/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1
InChIKey HDVAWXXJVMJBAR-VHSXEESVSA-N
SMILES [H][C@]12CCCCN1CCC[C@H]2CO
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 )
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ChEBI Ontology
Outgoing lupinine (CHEBI:28012) is a quinolizidine alkaloid (CHEBI:26515)
IUPAC Name
(1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol
Synonyms Sources
1S-cis-octahydro-2H-quinolizine-1-methanol ChEBI
Lupinine KEGG COMPOUND
Database Links Databases
C00002226 KNApSAcK
C10773 KEGG COMPOUND
LSM-19023 LINCS
View more database links
Registry Number Type Source
486-70-4 CAS Registry Number KEGG COMPOUND
Last Modified
25 February 2016
General Comment
2007-06-14 Confusion exists in the literature between lupinine and lupanine. Thus lupinine (this entry) is a bicyclic quinolizidine alkaloid whereas lupanine has a methylene-bridged dipyridodiazocine structure containing two quinolizidine systems (see, e.g., entry for 13-hydroxylupanine). Unfortunately the two terms are sometimes used synonomously.