MELEAGRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H23N5O4
Molecular Weight	433.4598
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CON1C2=C(C=CC=C2)[C@@]3(C=C(O)C(=O)N4\C(=C\C5=CN=CN5)C(=O)N[C@@]134)C(C)(C)C=C

InChI

InChIKey=JTJJJLSLKZFEPJ-ZAYCRUKZSA-N

InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26692349 | https://www.ncbi.nlm.nih.gov/pubmed/24312171

Meleagrin is an indole alkaloids, extracted from Penicillium chrysogenum mycelia, is a bacterial enoyl-acyl carrier protein reductase (FabI) inhibitor, and has at least has one additional mode of action that could have potential for treating multidrug-resistant bacteria. Also was shown, that this alkaloid is useful for the control of c-Met-dependent metastatic and invasive breast malignancies.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial enoyl-[acyl-carrier-protein] reductase 8 Target ID: CHEMBL2364678 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24312171	Inhibitor 8504		40.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi.	2016-02	26668029
The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Met-dependent breast cancer proliferation, migration and invasion.	2016-01-15	26692349
Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action.	2013	24312171

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Meleagrin with different range of concentrations (0 – 40 uM) inhibits HGF-induced proliferation of breast cancer cell lines: MDA-MB-231, MDA-MB-468, and BT-474, MCF7, MCF7-dox and T-47D as well as SKBR-3. Meleagrin also exhibited moderate cytotoxicity against the non-small cell lung cancer A-549 cells and the leukemia HL-60 cell line, with the IC50 values of 19.9 and 7.4 μM, respectively. The cytotoxic mechanisms of meleagrin was investigated by flow cytometric analysis. Meleagrin arrested the cell cycle through G2/M phase at the 5 and 10 μM.

Name

Type

Language

6-O-DEMETHYLOXALINE

Preferred Name

English

MELEAGRIN

Common Name

English

MELEAGRIN, (-)-

Common Name

English

(3E,7AR,12AS)-7A-(1,1-DIMETHYL-2-PROPEN-1-YL)-7A,12-DIHYDRO-6-HYDROXY-3-(1H-IMIDAZOL-5-YLMETHYLENE)-12-METHOXY-1H,5H-IMIDAZO(1',2':1,2)PYRIDO(2,3-B)INDOLE-2,5(3H)-DIONE

Systematic Name

English

1H,5H-IMIDAZO(1',2':1,2)PYRIDO(2,3-B)INDOLE-2,5(3H)-DIONE, 7A-(1,1-DIMETHYL-2-PROPEN-1-YL)-7A,12-DIHYDRO-6-HYDROXY-3-(1H-IMIDAZOL-5-YLMETHYLENE)-12-METHOXY-, (3E,7AR,12AS)-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Meleagrin