LAUROTETANINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H21NO4
Molecular Weight	327.3743
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC3=C(C=C(OC)C(O)=C3)C4=C(OC)C(OC)=CC(CCN1)=C24

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	327.3743
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8083812 | https://www.ncbi.nlm.nih.gov/pubmed/21809579 | https://www.ncbi.nlm.nih.gov/pubmed/22119096 | https://www.ncbi.nlm.nih.gov/pubmed/27086149

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27086149	Inhibitor 8297	132.0 µM [IC50]
Acetylcholinesterase 207 Target ID: CHEMBL4768 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22119096	Inhibitor 8297	3.2 µM [IC50]
Acidic alpha-glucosidase 3 Target ID: CHEMBL3513 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22119096	Inhibitor 8297	22.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27086149	Curative		Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21809579	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Alkaloids from roots and stems of Litsea cubeba].	2014 Oct	25751947
Cytotoxic Alkaloids from the Stem of Xylopia laevigata.	2016 Jul 8	27399666
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).	2016 Sep 15	27492195
Computer-Aided (13)C NMR Chemical Profiling of Crude Natural Extracts without Fractionation.	2017 May 26	28414230

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

(+)-laurotetanine exhibited strong antiplasmodial activities with IC(50) value of 0.189 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:55:07 UTC 2023` Edited by `admin` on `Fri Dec 15 17:55:07 UTC 2023`
Record UNII	SDW3N623LN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAUROTETANINE

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

NSC

106610