ISOCORYDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H23NO4
Molecular Weight	341.4009
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC3=CC=C(OC)C(O)=C3C4=C1C(CCN2C)=CC(OC)=C4OC

InChI

InChIKey=QELDJEKNFOQJOY-ZDUSSCGKSA-N

InChI=1S/C20H23NO4/c1-21-8-7-12-10-15(24-3)20(25-4)18-16(12)13(21)9-11-5-6-14(23-2)19(22)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-/m0/s1

HIDE SMILES / InChI

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0030184 | https://www.ncbi.nlm.nih.gov/pubmed/22623962

Isocorydine is a member of the class of compounds known as aporphines. Isocorydine is practically insoluble in water and weakly acidic. It is a naturally occurring plant metabolite which can be found in cherimoya and poppy. Isocorydine has generated interest as a potential anti-cancer compound for its ability to induce G2/M cell cycle arrest and apoptosis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell cycle G2/M phase transition 21 Target ID: GO:0044839 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22623962	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22623962	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Effects of isocorydine on contraction of the rabbit oviduct smooth muscle].	1990	2099095
Isocorydine inhibits cell proliferation in hepatocellular carcinoma cell lines by inducing G2/m cell cycle arrest and apoptosis.	2012	22623962
Isocorydine targets the drug-resistant cellular side population through PDCD4-related apoptosis in hepatocellular carcinoma.	2012 Sep 25	22714713
[Extraction and purification of isocorydine from Dicranostigma leptopodum].	2013 May	24218977
[Research on anticancer activity of isocorydine and its derivatives].	2017 Aug	29171235

Patents

Sample Use Guides

In Vivo Use Guide

In a pharmacokinetic study, Isocorydine was administered to rats at an oral dose of 20 mg/kg and intravenous injection of 5 mg/kg.

Route of Administration: Other

In Vitro Use Guide

The human HCC cell lines SMMC-7721, MHCC-97L and Huh7 were cultured in Dulbecco's Modified Eagle's Medium containing 10% heat-inactivated fetal bovine serum and supplemented with 100 IU/mL penicillin G and 100 micro-g/mL streptomycin. Incubations were conducted at 37 deg-C in a 5% CO2 atmosphere. Cell cultures were incubated with various concentrations (0 - 459 micro-g/mL) of Isocorydine for 48 hours. Isocorydine exhibited dose-dependent growth inhibition profile. IC50 values for each cell line were determined as 200, 250 and 300 µg/ml for SMMC-7721, Huh7 and PLC/PRF/5, respectively.

Name

Type

Language

ISOCORYDINE

Common Name

English

LUTEANIN

Common Name

English

UZOKORIDIN

Common Name

English

S-(+)-ISOCORYDINE

Common Name

English

NSC-32979

Code

English

ISOCORYDINE [MI]

Common Name

English

LUTEANINE

Common Name

English

(S)-(+)-ISOCORYDINE

Common Name

English

4H-DIBENZO(DE,G)QUINOLIN-11-OL, 5,6,6A,7-TETRAHYDRO-1,2,10-TRIMETHOXY-6-METHYL-, (6AS)-

Common Name

English

6A-.ALPHA.-APORPHIN-11-OL, 1,2,10-TRIMETHOXY-

Common Name

English

4H-DIBENZO(DE,G)QUINOLIN-11-OL, 5,6,6A,7-TETRAHYDRO-1,2,10-TRIMETHOXY-6-METHYL-, (S)-

Common Name

English

D-ISOCORYDINE

Common Name

English

NSC-645316

Code

English

ISOCORYDINE, (+)-

Common Name

English

L-(+)-ISOCORYDINE

Common Name

English

(+)-(S)-ISOCORYDINE

Common Name

English

ARTABOTRINE

Common Name

English

ARTABOTRIN

Common Name

English

LINDCARPINE, N,O-DIMETHYL-

Common Name

English

(+)-ISOCORYDINE

Common Name

English

APORPHIN-11-OL, 1,2,10-TRIMETHOXY-

Systematic Name

English

Code System Code Type Description

CAS

475-67-2