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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO4
Molecular Weight 327.3751
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAUROTETANINE

SMILES

COc1cc-2c(C[C@@]3([H])c4c(CCN3)cc(c(c24)OC)OC)cc1O

InChI

InChIKey=GVVXPMORGFYVOO-ZDUSSCGKSA-N
InChI=1S/C19H21NO4/c1-22-15-9-12-11(7-14(15)21)6-13-17-10(4-5-20-13)8-16(23-2)19(24-3)18(12)17/h7-9,13,20-21H,4-6H2,1-3H3/t13-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H21NO4
Molecular Weight 327.3751
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Laurotetanine is an alkaloid isolated from the leaves of Peumus boldus and other plants. It was demonstrated that laurotetanine from Beilschmiedia species possess an anti-acetylcholinesterase (AChE), anti-α-glucosidase, anti-leishmanial and anti-fungal activities. Laurotetanine exhibits antiplasmodial activity and good antioxidant activities also. It relaxed the rat thoracic aorta mainly by suppressing the Ca2+ influx through both voltage- and receptor-operated calcium channels. It showed significant anti-tumor metastatic activities.

Originator

Sources: DOI: 10.1002/cber.189002302331

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
132.0 µM [IC50]
3.2 µM [IC50]
22.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Alkaloids from roots and stems of Litsea cubeba].
2014 Oct
In vitro antiplasmodial and antioxidant activities of bisbenzylisoquinoline alkaloids from Alseodaphne corneri Kosterm.
2016 Apr
Cytotoxic Alkaloids from the Stem of Xylopia laevigata.
2016 Jul 8
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
2016 Sep 15
Computer-Aided (13)C NMR Chemical Profiling of Crude Natural Extracts without Fractionation.
2017 May 26
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
(+)-laurotetanine exhibited strong antiplasmodial activities with IC(50) value of 0.189 uM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:23:18 UTC 2021
Edited
by admin
on Sat Jun 26 12:23:18 UTC 2021
Record UNII
SDW3N623LN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAUROTETANINE
MI  
Common Name English
NSC-106610
Code English
(6AS)-5,6,6A,7-TETRAHYDRO-1,2,10-TRIMETHOXY-4H-DIBENZO(DE,G)QUINOLIN-9-OL
Common Name English
LAUROTETANINE [MI]
Common Name English
LITSOEINE
Common Name English
Code System Code Type Description
CAS
128-76-7
Created by admin on Sat Jun 26 12:23:18 UTC 2021 , Edited by admin on Sat Jun 26 12:23:18 UTC 2021
PRIMARY
MESH
C008256
Created by admin on Sat Jun 26 12:23:18 UTC 2021 , Edited by admin on Sat Jun 26 12:23:18 UTC 2021
PRIMARY
MERCK INDEX
M6713
Created by admin on Sat Jun 26 12:23:18 UTC 2021 , Edited by admin on Sat Jun 26 12:23:18 UTC 2021
PRIMARY Merck Index
PUBCHEM
31415
Created by admin on Sat Jun 26 12:23:18 UTC 2021 , Edited by admin on Sat Jun 26 12:23:18 UTC 2021
PRIMARY
FDA UNII
SDW3N623LN
Created by admin on Sat Jun 26 12:23:18 UTC 2021 , Edited by admin on Sat Jun 26 12:23:18 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT