trimethoprim (CHEBI:45924)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	trimethoprim

ChEBI ID	CHEBI:45924

Definition	An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.

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

Secondary ChEBI IDs	CHEBI:45921, CHEBI:9731

Supplier Information

Download	Molfile XML SDF

more structures >>

Wikipedia	License

Read full article at Wikipedia

Formula

C14H18N4O3

Net Charge

Average Mass

290.318

Monoisotopic Mass

290.13789

InChI

InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)

InChIKey

IEDVJHCEMCRBQM-UHFFFAOYSA-N

SMILES

C=1(CC=2C(=NC(N)=NC2)N)C=C(C(OC)=C(C1)OC)OC

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	drug allergen Any drug which causes the onset of an allergic reaction. antibacterial drug A drug used to treat or prevent bacterial infections. EC 1.5.1.3 (dihydrofolate reductase) inhibitor An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3). xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	drug allergen Any drug which causes the onset of an allergic reaction. antibacterial drug A drug used to treat or prevent bacterial infections. diuretic An agent that promotes the excretion of urine through its effects on kidney function.

ChEBI Ontology
Outgoing	trimethoprim (CHEBI:45924) has role antibacterial drug (CHEBI:36047) trimethoprim (CHEBI:45924) has role diuretic (CHEBI:35498) trimethoprim (CHEBI:45924) has role drug allergen (CHEBI:88188) trimethoprim (CHEBI:45924) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683) trimethoprim (CHEBI:45924) has role environmental contaminant (CHEBI:78298) trimethoprim (CHEBI:45924) has role xenobiotic (CHEBI:35703) trimethoprim (CHEBI:45924) is a aminopyrimidine (CHEBI:38338) trimethoprim (CHEBI:45924) is a methoxybenzenes (CHEBI:51683)

Incoming	6-chlorotrimethoprim (CHEBI:351351) has functional parent trimethoprim (CHEBI:45924) 6-hydroxytrimethoprim (CHEBI:58969) has functional parent trimethoprim (CHEBI:45924) co-trimoxazole (CHEBI:3770) has part trimethoprim (CHEBI:45924) 5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl group (CHEBI:55508) is substituent group from trimethoprim (CHEBI:45924)

IUPAC Name

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Synonyms	Sources
2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine	NIST Chemistry WebBook
5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine	NIST Chemistry WebBook
Proloprim	ChemIDplus
Trimethoprim	KEGG COMPOUND
TRIMETHOPRIM	PDBeChem
Trimpex	ChemIDplus

Last Modified

20 June 2017

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag