fusarithioamide A (CHEBI:141359)

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ChEBI Name	fusarithioamide A

ChEBI ID	CHEBI:141359

Definition	A member of the class of benzamides that is 2-aminobenzoic acid in which the hydrogen atom of the carboxy group has been substituted by a [(1S)-1-hydroxy-3-mercaptopropyl]nitrilo group and in which one of the the hydrogens of the amino group has been substituted by a (2R)-2-aminopropanoyl group. It is a metabolite isolated from the endophytic fungus, Fusarium chlamydosporium.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	R. Stephan

Supplier Information

Download	Molfile XML SDF

Formula

C13H19N3O3S

Net Charge

Average Mass

297.375

Monoisotopic Mass

297.11471

InChI

InChI=1S/C13H19N3O3S/c1-8(14)12(18)15-10-5-3-2-4-9(10)13(19)16-11(17)6-7-20/h2-5,8,11,17,20H,6-7,14H2,1H3,(H,15,18)(H,16,19)/t8-,11+/m1/s1

InChIKey

DQGIXJCPVVNGMY-KCJUWKMLSA-N

SMILES

C[C@H](C(NC1=CC=CC=C1C(N[C@H](CCS)O)=O)=O)N

Metabolite of Species	Details
Fusarium chlamydosporum (NCBI:txid86545)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	fusarithioamide A (CHEBI:141359) has functional parent D-alanine (CHEBI:15570) fusarithioamide A (CHEBI:141359) has role antifungal agent (CHEBI:35718) fusarithioamide A (CHEBI:141359) has role antineoplastic agent (CHEBI:35610) fusarithioamide A (CHEBI:141359) has role fungal metabolite (CHEBI:76946) fusarithioamide A (CHEBI:141359) is a benzamides (CHEBI:22702) fusarithioamide A (CHEBI:141359) is a organic hydroxy compound (CHEBI:33822) fusarithioamide A (CHEBI:141359) is a primary amino compound (CHEBI:50994) fusarithioamide A (CHEBI:141359) is a secondary carboxamide (CHEBI:140325) fusarithioamide A (CHEBI:141359) is a thiol (CHEBI:29256)

IUPAC Names

2-(D-alanylamino)-N-[(1S)-1-hydroxy-3-mercaptopropyl]benzamide

2-(D-alanylamino)-N-[(1S)-1-hydroxy-3-sulfanylpropyl]benzamide

Registry Number	Type	Source
30208318	Reaxys Registry Number	Reaxys

Last Modified

11 June 2019