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

COC1=CC2=C(C=C1)C3=C4[C@H](CC(C)(C)OO[C@H](C=C(C)C)N24)N5C(=O)[C@@H]6CCCN6C(=O)[C@]5(O)[C@H]3OCC=C(C)C

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 2596

PubMed

Title	Date	PubMed
Central effects of the neurotropic mycotoxin fumitremorgin A in the rabbit. (II). Effects on the brain stem.	1990-02	2313930
Central effects of the neurotropic mycotoxin fumitremorgin A in the rabbit (I). Effects on the spinal cord.	1989-06	2770054
Abnormal behavioral effects elicited by a neurotropic mycotoxin, fumitremorgin A in mice.	1984-12	6152472
Biochemical investigation on the abnormal behaviors induced by fumitremorgin A, a tremorgenic mycotoxin to mice.	1983-10	6198505
Chemistry of tremorogenic metabolites. I. Fumitremorgin A from Aspergillus fumigatus.	1980-01	6988091
Production of the Tremorgenic Mycotoxins Verruculogen and Fumitremorgin B by Penicillium piscarium Westling.	1977-03	16345234
Tremorgenic toxins from Aspergillus fumigatus Fres.	1971-08	5122678

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 `Mon Mar 31 21:43:05 GMT 2025` Edited by `admin` on `Mon Mar 31 21:43:05 GMT 2025`
Record UNII	ZR1C7949XT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FUMITREMORGEN A

Preferred Name

English

FUMITREMORGIN A

Common Name

English

Code System Code Type Description

CHEBI

72766