CHEBI:18328 - 13-hydroxylupanine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 13-hydroxylupanine
ChEBI ID CHEBI:18328
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:751, CHEBI:11321, CHEBI:19148
Supplier Information
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Formula C15H24N2O2
Net Charge 0
Average Mass 264.36334
Monoisotopic Mass 264.18378
InChI InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12+,13-,14-/m1/s1
InChIKey JVYKIBAJVKEZSQ-RKQHYHRCSA-N
SMILES [H][C@]12CCCC(=O)N1C[C@H]1C[C@@H]2CN2CC[C@H](O)C[C@]12[H]
ChEBI Ontology
Outgoing 13-hydroxylupanine (CHEBI:18328) has functional parent lupanine (CHEBI:28193)
13-hydroxylupanine (CHEBI:18328) is a organic heterotetracyclic compound (CHEBI:38163)
13-hydroxylupanine (CHEBI:18328) is conjugate base of 13-hydroxylupaninium (CHEBI:58446)
Incoming 13-hydroxylupaninium (CHEBI:58446) is conjugate acid of 13-hydroxylupanine (CHEBI:18328)
IUPAC Name
(2S,7R,7aR,14R,14aR)-2-hydroxydodecahydro-2H,11H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one
Synonyms Sources
(+)-13alpha-Hydroxylupanine KEGG COMPOUND
13-Hydroxylupanine KEGG COMPOUND
13-Hydroxylupinine KEGG COMPOUND
13α-hydroxyspartein-2-one ChEBI
Manual Xrefs Databases
C00002221 KNApSAcK
C02621 KEGG COMPOUND
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Registry Number Type Source
15358-48-2 CAS Registry Number KEGG COMPOUND
Last Modified
04 August 2014
General Comment
2007-06-14 Confusion exists in the literature between lupinine and lupanine. Thus lupinine is a bicyclic quinolizidine alkaloid whereas lupanine has a methylene-bridged dipyridodiazocine structure containing two quinolizidine systems; the current compound is an example. Unfortunately the two terms are sometimes used synonomously.