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Details

Stereochemistry RACEMIC
Molecular Formula C10H19NO
Molecular Weight 169.264
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

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

SMILES

[H][C@]12CCCCN1CCC[C@H]2CO

InChI

InChIKey=HDVAWXXJVMJBAR-VHSXEESVSA-N
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

HIDE SMILES / InChI
Molecular Formula C10H19NO
Molecular Weight 169.264
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Lupinine is a bitter tasting quinolizidine alkaloid present in Lupinus species of the Family Fabaceae. It has been shown to lower the locomotion excitation brought on by ethanol anesthesia in mice. Lupinine has also shown some ability to inhibit human and rabbit cholinesterases.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Cholinesterase
14
Target ID: P06276
Gene ID: 590.0
Gene Symbol: BCHE
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine.
2001 Mar
Indolizidine and quinolizidine alkaloids.
2001 Oct
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.
2002 Jun
Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives.
2004 Jul 5
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
2004 Jul-Aug
Cholinesterase hydrolysis of substituted lupinine benzoates.
2008 Mar-Apr
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.
2008 Sep-Oct
Epiquinamide: a poison that wasn't from a frog that was.
2009 Feb 27
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.
2009 Oct 26
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.
2010 Feb 5
Patents

Patents

07569583
6
20070197584
3
20080187936
3
20090269772
13
20120015378
3
20140206660
3

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:00:45 UTC 2023
Edited
by admin
on Sat Dec 16 08:00:45 UTC 2023
Record UNII
F74RAC8A5Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LUPININE, (±)-
Common Name English
2H-QUINOLIZINE-1-METHANOL, OCTAHYDRO-, (1R-TRANS)-(±)-
Systematic Name English
(±)-LUPININE
Common Name English
LUPININE DL-FORM [MI]
Common Name English
2H-QUINOLIZINE-1-METHANOL, OCTAHYDRO-, (1R,9AR)-REL-
Systematic Name English
Code System Code Type Description
CAS
10248-30-3
Created by admin on Sat Dec 16 08:00:45 UTC 2023 , Edited by admin on Sat Dec 16 08:00:45 UTC 2023
PRIMARY
MERCK INDEX
m6939
Created by admin on Sat Dec 16 08:00:45 UTC 2023 , Edited by admin on Sat Dec 16 08:00:45 UTC 2023
PRIMARY Merck Index
FDA UNII
F74RAC8A5Q
Created by admin on Sat Dec 16 08:00:45 UTC 2023 , Edited by admin on Sat Dec 16 08:00:45 UTC 2023
PRIMARY
PUBCHEM
91461
Created by admin on Sat Dec 16 08:00:45 UTC 2023 , Edited by admin on Sat Dec 16 08:00:45 UTC 2023
PRIMARY
NIH
NCATS
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