LUPANINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H24N2O
Molecular Weight	248.3639
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CCC[C@@H]2[C@H]3C[C@@H](CN12)[C@@H]4CCCCN4C3

InChI

InChIKey=JYIJIIVLEOETIQ-XDQVBPFNSA-N

InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H24N2O
Molecular Weight	248.3639
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Determination of quinolizidine alkaloids in different Lupinus species by NACE using UV and MS detection.	2010-12-15	20580181
Overproduced Brucella abortus PdhS-mCherry forms soluble aggregates in Escherichia coli, partially associating with mobile foci of IbpA-YFP.	2010-09-28	20920169
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.	2009-10-26	19857257
Periplasmically-exported lupanine hydroxylase undergoes transition from soluble to functional inclusion bodies in Escherichia coli.	2009-04-01	19467626
Alkaloids and saponins as cytochrome P450 inhibitors from blue cohosh (Caulophyllum thalictroides) in an in vitro assay.	2009-03	19137500
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.	2008-12-02	19040102
Quinolizidine alkaloids in seeds of lupin genotypes of different origins.	2008-05-28	18433102
Evaluation of total quinolizidine alkaloids content in lupin flours, lupin-based ingredients, and foods.	2008-04	18324702
Influence of plant secondary metabolites on in vitro oxidation of methyl ferulate with cell wall peroxidases from lupine apoplast.	2008	17928101
Hypoglycaemic effect of quinolizidine alkaloids--lupanine and 2-thionosparteine on non-diabetic and streptozotocin-induced diabetic rats.	2007-06-22	17379208
Alkaloid profiles, concentration, and pools in velvet lupine (Lupinus leucophyllus) over the growing season.	2007-01	17146716
Phloem alkaloid tolerance allows feeding on resistant Lupinus angustifolius by the aphid Myzus persicae.	2006-09	16906361
Chemotaxonomy of Portuguese Ulex: quinolizidine alkaloids as taxonomical markers.	2006-09	16876210
Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food.	2006-04-21	16359686
Cytisus scoparius link--a natural antioxidant.	2006-03-16	16542432
Histological evaluation of brain damage caused by crude quinolizidine alkaloid extracts from lupines.	2005-10	16136497
A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry.	2005-07-27	16042152
Do naïve ruminants degrade alkaloids in the rumen?	2005-04	16124250
Quinolizidine alkaloids isolated from Lupinus species enhance insulin secretion.	2004-11-03	15507230
Comparison of plasma disposition of alkaloids after lupine challenge in cattle that had given birth to calves with lupine-induced arthrogryposis or clinically normal calves.	2004-11	15566098
The effect of body condition on disposition of alkaloids from silvery lupine (Lupinus argenteus pursh) in sheep.	2004-09	15446497
Mass spectrometry of bisquinolizidine alkaloids: 2- and 17-cyano-substituted derivatives of sparteine and lupanine.	2004-05	15170750
Quinolizidine alkaloid profiles of two taxa of Teline maderensis.	2004-01-10	14713148
The quinohaemoprotein lupanine hydroxylase from Pseudomonas putida.	2003-04-11	12686118
Cloning, sequencing and heterologous expression of the gene for lupanine hydroxylase, a quinocytochrome c from a Pseudomonas sp.	2002-10-15	12119046
Alkaloid profile of leaves and seeds of Lupinus hintonii C. P. Smith.	2002-06-18	12064721
Bacterial removal of quinolizidine alkaloids and other carbon sources from a Lupinus albus aqueous extract.	2002-04-10	11929291
Chemical composition, nutritive value, and toxicology evaluation of Mexican wild lupins.	2001-11	11714325
Mineralogical and chemical interactions of soils eaten by chimpanzees of the Mahale Mountains and Gombe Stream National Parks, Tanzania.	2001-02	14768816
Immunolocalization of alkaloids and X-ray microanalysis of elements in lupin seeds.	2001	11732315

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:33:56 GMT 2025` Edited by `admin` on `Mon Mar 31 19:33:56 GMT 2025`
Record UNII	183KU7535A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUPANINE D-FORM

Preferred Name

English

LUPANINE

Common Name

English

LUPANIN

Common Name

English

LUPANINE, (+)-

Common Name

English

7,14-METHANO-2H,11H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCIN-11-ONE, DODECAHYDRO-, (7S,7AR,14S,14AS)-

Common Name

English

LUPANINE, D-

Common Name

English

2-OXOSPARTEINE

Common Name

English

(+)-2-OXOSPARTEINE

Common Name

English

LUPANINE D-FORM [MI]

Common Name

English

(+)-LUPANINE

Common Name

English

Code System Code Type Description

PUBCHEM

91471