FUMITREMORGIN C

Inquiry

For Research Use Only.

Category

Alkaloids

Cat.No.

NP0401

CAS

118974-02-0

Product Name

FUMITREMORGIN C

Structure

Product Details

Description

Fumitremorgin C, isolated from Aspergillus fumigatus, is 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.

Synonyms

tryproquivaline D (2'S-(2'alpha,9'alpha(4R*(S*)),9'abeta))-isomer; tryproquivaline L (9'R-(9'alpha(R*),9'abeta))-isomer; tryproquivaline M (2'S-(2'alpha,9'alpha(4R*(S*)),9'abeta))-isomer; tryproquivaline N (2'S-(2'alpha,9'alpha(R*),9'abeta))-isomer; tryptoquivaline; (5aS,12S,14aS)-1,2,3,5a,6,11,12,14a-Octahydro-9-methoxy-12-(2-methyl-1-propen-1-yl)-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione

IUPAC Name

(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione

Molecular Weight

379.45

Molecular Formula

C22H25N3O3

Canonical SMILES

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

InChI

InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1

InChIKey

DBEYVIGIPJSTOR-FHWLQOOXSA-N

Boiling Point

642.9±55.0°C at 760 Torr

Melting Point

259.5-260.5°C

Purity

≥95%

Density

1.34±0.1 g/cm3

Solubility

Slightly soluble in DMSO, Chloroform

Appearance

White to Light Yellow Solid

Storage

Store at -20°C

Definition

ChEBI: An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter.

Form

Powder

pKa

17.16±0.40(Predicted)

Safety Statements

22-24/25

Uses

Fumitremorgin C is a tremorgenic mycotoxin isolated from aspergillus fumigatus. Recent research has determined fumitremorgin C as a potent inhibitor of the breast cancer resistance protein BCRP/ABCG2 multidrug transporter.

WGK Germany

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