FUMITREMORGIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H41N3O7
Molecular Weight	579.6838
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCCN1C(=O)[C@]3(O)[C@@H](OCC=C(C)C)C4=C5N([C@H](OOC(C)(C)C[C@]5([H])N3C2=O)C=C(C)C)C6=CC(OC)=CC=C46

InChI

InChIKey=ACGHJVZDNQZJOV-BMOJZYMJSA-N

InChI=1S/C32H41N3O7/c1-18(2)12-14-40-28-26-21-11-10-20(39-7)16-23(21)34-25(15-19(3)4)41-42-31(5,6)17-24(27(26)34)35-29(36)22-9-8-13-33(22)30(37)32(28,35)38/h10-12,15-16,22,24-25,28,38H,8-9,13-14,17H2,1-7H3/t22-,24-,25+,28-,32+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C32H41N3O7
Molecular Weight	579.6838
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3735799
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6152472 | https://www.ncbi.nlm.nih.gov/pubmed/6198505

Fumitremorgin A (FTA) is the most potent mycotoxin among fumitremorgins, a series of tremorgenic toxins isolated from Aspergillus fumigatus by Yamazaki et al. in 1971. When injected intravenously in experimental animals, FTA causes tremor and generalized tonic-clonic convulsion. Both dopaminergic and gamma-aminobutyric acid (GABA)-ergic systems are involved in FTA-induced abnormal behaviors. On the other hand insignificant participation of serotonergic mechanism in modulation of those behavioral states elicited by FTA is conclusively suggested.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Tremorgenic toxins from Aspergillus fumigatus Fres.	1971 Aug	5122678
Production of the Tremorgenic Mycotoxins Verruculogen and Fumitremorgin B by Penicillium piscarium Westling.	1977 Mar	16345234
Chemistry of tremorogenic metabolites. I. Fumitremorgin A from Aspergillus fumigatus.	1980 Jan	6988091
Biochemical investigation on the abnormal behaviors induced by fumitremorgin A, a tremorgenic mycotoxin to mice.	1983 Oct	6198505
Abnormal behavioral effects elicited by a neurotropic mycotoxin, fumitremorgin A in mice.	1984 Dec	6152472
Central effects of the neurotropic mycotoxin fumitremorgin A in the rabbit (I). Effects on the spinal cord.	1989 Jun	2770054
Central effects of the neurotropic mycotoxin fumitremorgin A in the rabbit. (II). Effects on the brain stem.	1990 Feb	2313930

Patents

Sample Use Guides

In Vivo Use Guide

Fumitremorgin A (10-200 ug/kg, i.v.) caused clonic and tonic convulsion accompanied by nystagmus and miosis in conscious rabbits, after a latent period.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:42:37 GMT 2023` Edited by `admin` on `Sat Dec 16 07:42:37 GMT 2023`
Record UNII	ZR1C7949XT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FUMITREMORGIN A

Common Name

English

FUMITREMORGEN A

Common Name

English

Code System Code Type Description

CHEBI

72766