CHEBI:27744 - glyphosate

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ChEBI Name glyphosate
ChEBI ID CHEBI:27744
Definition A phosphonic acid resulting from the formal oxidative coupling of the methyl group of methylphosphonic acid with the amino group of glycine. It is one of the most commonly used herbicdes worldwide, and the only one to target the enzyme 5-enolpyruvyl-3-shikimate phosphate synthase (EPSPS).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5510, CHEBI:24423, CHEBI:43013
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Formulae C3H8NO5P
C3H8NO5P
Net Charge 0
Average Mass 169.07310
Monoisotopic Mass 169.014
InChI InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)
InChIKey XDDAORKBJWWYJS-UHFFFAOYSA-N
SMILES OC(=O)CNCP(O)(O)=O
Roles Classification
Chemical Role(s): inorganic acid
A Bronsted acid derived from one or more inorganic compounds. Inorganic acids (also known as mineral acids) form hydrons and conjugate base ions when dissolved in water.
(via pnictogen oxoacid )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 2.5.1.19 (3-phosphoshikimate 1-carboxyvinyltransferase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of 3-phosphoshikimate 1-carboxyvinyltransferase (EC 2.5.1.19).
fungicide
A substance used to destroy fungal pests.
(via phosphonic acid )
Application(s): agrochemical
An agrochemical is a substance that is used in agriculture or horticulture.
herbicide
A substance used to destroy plant pests.
fungicide
A substance used to destroy fungal pests.
(via phosphonic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing glyphosate (CHEBI:27744) has role agrochemical (CHEBI:33286)
glyphosate (CHEBI:27744) has role EC 2.5.1.19 (3-phosphoshikimate 1-carboxyvinyltransferase) inhibitor (CHEBI:20569)
glyphosate (CHEBI:27744) has role herbicide (CHEBI:24527)
glyphosate (CHEBI:27744) is a glycine derivative (CHEBI:24373)
glyphosate (CHEBI:27744) is a phosphonic acid (CHEBI:44976)
glyphosate (CHEBI:27744) is conjugate acid of glyphosate(1−) (CHEBI:133673)
glyphosate (CHEBI:27744) is conjugate acid of glyphosate(2−) (CHEBI:67052)
Incoming glyphosate(1−) (CHEBI:133673) is conjugate base of glyphosate (CHEBI:27744)
glyphosate(2−) (CHEBI:67052) is conjugate base of glyphosate (CHEBI:27744)
IUPAC Name
N-(phosphonomethyl)glycine
Synonym Source
Glyphosate KEGG COMPOUND
Manual Xrefs Databases
373 PPDB
c0134 UM-BBD
C01705 KEGG COMPOUND
DB04539 DrugBank
glyphosate Alan Wood's Pesticides
Glyphosate Wikipedia
GPF PDBeChem
GPJ PDBeChem
View more database links
Registry Numbers Types Sources
1071-83-6 CAS Registry Number KEGG COMPOUND
1071-83-6 CAS Registry Number Alan Wood's Pesticides
1071-83-6 CAS Registry Number ChemIDplus
2045054 Beilstein Registry Number Beilstein
279222 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
27758090 PubMed citation Europe PMC
28266132 PubMed citation Europe PMC
28474816 PubMed citation Europe PMC
28643882 PubMed citation Europe PMC
28711546 PubMed citation Europe PMC
Last Modified
20 July 2017