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Details

Stereochemistry RACEMIC
Molecular Formula C15H24N2O
Molecular Weight 248.3639
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUPANINE, (±)-

SMILES

[H][C@]12CN3CCCC[C@@]3([H])[C@]([H])(CN4C(=O)CCC[C@]14[H])C2

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

PubMed

TitleDatePubMed
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
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
Do naïve ruminants degrade alkaloids in the rumen?
2005 Apr
A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry.
2005 Jul-Aug
Histological evaluation of brain damage caused by crude quinolizidine alkaloid extracts from lupines.
2005 Oct
Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food.
2006 Apr 21
Cytisus scoparius link--a natural antioxidant.
2006 Mar 16
Phloem alkaloid tolerance allows feeding on resistant Lupinus angustifolius by the aphid Myzus persicae.
2006 Sep
Chemotaxonomy of Portuguese Ulex: quinolizidine alkaloids as taxonomical markers.
2006 Sep
Alkaloid profiles, concentration, and pools in velvet lupine (Lupinus leucophyllus) over the growing season.
2007 Jan
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 Dec 16 09:13:17 GMT 2023
Edited
by admin
on Sat Dec 16 09:13:17 GMT 2023
Record UNII
9K48888N9P
Record Status Validated (UNII)
Record Version
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Name Type Language
LUPANINE, (±)-
Common Name English
(±)-LUPANINE
Common Name English
(±)-2-OXOSPARTEINE
Common Name English
(RAC)-2-OXOSPARTEINE
Common Name English
7,14-METHANO-2H,11H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCIN-11-ONE, DODECAHYDRO-, (7R,7AS,14R,14AR)-REL-
Systematic Name English
DL-LUPANINE
Common Name English
LUPANINE DL-FORM [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m6937
Created by admin on Sat Dec 16 09:13:17 GMT 2023 , Edited by admin on Sat Dec 16 09:13:17 GMT 2023
PRIMARY Merck Index
CAS
4356-43-8
Created by admin on Sat Dec 16 09:13:17 GMT 2023 , Edited by admin on Sat Dec 16 09:13:17 GMT 2023
PRIMARY
FDA UNII
9K48888N9P
Created by admin on Sat Dec 16 09:13:17 GMT 2023 , Edited by admin on Sat Dec 16 09:13:17 GMT 2023
PRIMARY
PUBCHEM
91471
Created by admin on Sat Dec 16 09:13:17 GMT 2023 , Edited by admin on Sat Dec 16 09:13:17 GMT 2023
PRIMARY