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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 of FUMITREMORGIN A

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

ConditionModalityTargetsHighest PhaseProduct

PubMed

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
Record UNII
ZR1C7949XT
Record Status Validated (UNII)
Record Version