Fumitremorgin C

Molecular Formula

C22H25N3O3

M.W.

379.46

CAS number

118974-02-0

Details

Source

Aspergillus sp.

Fermentek product Code

FUC-001

Brand/grade

For research

Specifications

Appearance

Crystalline solid

Purity by HPLC

≥98% ; refer to CoA for more data

Purity By TLC

≥98% ; refer to CoA for more data

Melting point

255°C - 271°C

Solubility test

Clear colorless solution at 10mg/ml of
Methanol or Acetonitrile.

Chemical identification

Names and identifiers

Synonyms:

Chemical names:

IUPAC: (5aS,12S,14aS)-9-Methoxy-12-(2-methyl-1-propen-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione

RTECS# UY8709670

EU number

Not listed

Chemical name

Fumitremorgin C

Description

Fumitremorgin C is a tremorgenic mycotoxin isolated from Aspergillus fumigatus. Recent research has recognized Fumitremorgin C as a potent and specific inhibitor of the breast cancer resistance protein (BCRP/ABCG2) multidrug transporter. It reverses multidrug resistance mediated by BCRP and increases cytotoxicity of several anticancer agents in vitro.

InChl Key

DBEYVIGIPJSTOR-FHWLQOOXSA-N

Canonical SMILES

CC(=CC1C2=C(CC3N1C(=O)C4CCCN4C3=O)C5=C(N2)C=C(C=C5)OC)C

Isomeric SMILES

CC(=C[C@H]1C2=C(C[C@@H]3N1C(=O)[C@@H]4CCCN4C3=O)C5=C(N2)C=C(C=C5)OC)C

Further Information

Solubility ( literature )

Soluble in Ethanol, Methanol, DMF, DMSO Chloroform.

Negligible solubility ( 35 mg in 1 liter water @25°C) has been reported.

Compound Classification

Breast cancer resistance protein inhibitor