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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24N2O
Molecular Weight 248.3644
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUPANINE

SMILES

C1CCN2C[C@]3([H])C[C@@]([H])(CN4[C@]3([H])CCCC4=O)[C@]2([H])C1

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 248.3644
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Immunolocalization of alkaloids and X-ray microanalysis of elements in lupin seeds.
2001
Mineralogical and chemical interactions of soils eaten by chimpanzees of the Mahale Mountains and Gombe Stream National Parks, Tanzania.
2001 Feb
Chemical composition, nutritive value, and toxicology evaluation of Mexican wild lupins.
2001 Nov
Bacterial removal of quinolizidine alkaloids and other carbon sources from a Lupinus albus aqueous extract.
2002 Apr 10
Alkaloid profile of leaves and seeds of Lupinus hintonii C. P. Smith.
2002 Mar-Apr
Cloning, sequencing and heterologous expression of the gene for lupanine hydroxylase, a quinocytochrome c from a Pseudomonas sp.
2002 Oct 15
Quinolizidine alkaloid profiles of two taxa of Teline maderensis.
2003 Nov-Dec
Mass spectrometry of bisquinolizidine alkaloids: 2- and 17-cyano-substituted derivatives of sparteine and lupanine.
2004 May
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 Nov
Quinolizidine alkaloids isolated from Lupinus species enhance insulin secretion.
2004 Nov 3
The effect of body condition on disposition of alkaloids from silvery lupine (Lupinus argenteus pursh) in sheep.
2004 Sep
A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry.
2005 Jul-Aug
Hypoglycaemic effect of quinolizidine alkaloids--lupanine and 2-thionosparteine on non-diabetic and streptozotocin-induced diabetic rats.
2007 Jun 22
Influence of plant secondary metabolites on in vitro oxidation of methyl ferulate with cell wall peroxidases from lupine apoplast.
2008
Evaluation of total quinolizidine alkaloids content in lupin flours, lupin-based ingredients, and foods.
2008 Apr
Quinolizidine alkaloids in seeds of lupin genotypes of different origins.
2008 May 28
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.
2008 Sep-Oct
Periplasmically-exported lupanine hydroxylase undergoes transition from soluble to functional inclusion bodies in Escherichia coli.
2009 Apr 1
Alkaloids and saponins as cytochrome P450 inhibitors from blue cohosh (Caulophyllum thalictroides) in an in vitro assay.
2009 Mar
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.
2009 Oct 26
Determination of quinolizidine alkaloids in different Lupinus species by NACE using UV and MS detection.
2010 Dec 15
Overproduced Brucella abortus PdhS-mCherry forms soluble aggregates in Escherichia coli, partially associating with mobile foci of IbpA-YFP.
2010 Sep 28
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:58:52 UTC 2021
Edited
by admin
on Sat Jun 26 09:58:52 UTC 2021
Record UNII
183KU7535A
Record Status Validated (UNII)
Record Version
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Name Type Language
LUPANINE
Common Name English
LUPANIN
Common Name English
LUPANINE D-FORM
MI  
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
Created by admin on Sat Jun 26 09:58:52 UTC 2021 , Edited by admin on Sat Jun 26 09:58:52 UTC 2021
PRIMARY
MERCK INDEX
M6937
Created by admin on Sat Jun 26 09:58:52 UTC 2021 , Edited by admin on Sat Jun 26 09:58:52 UTC 2021
PRIMARY Merck Index
FDA UNII
183KU7535A
Created by admin on Sat Jun 26 09:58:52 UTC 2021 , Edited by admin on Sat Jun 26 09:58:52 UTC 2021
PRIMARY
CAS
550-90-3
Created by admin on Sat Jun 26 09:58:52 UTC 2021 , Edited by admin on Sat Jun 26 09:58:52 UTC 2021
PRIMARY
MESH
C008298
Created by admin on Sat Jun 26 09:58:52 UTC 2021 , Edited by admin on Sat Jun 26 09:58:52 UTC 2021
PRIMARY
Related Record Type Details
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