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 herbicides 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
Supplier Information ChemicalBook:CB7680517, eMolecules:498956, ZINC000003872713
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Glyphosate (IUPAC name: N-(phosphonomethyl)glycine) is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). Glyphosate-based herbicides are used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000. Farmers quickly adopted glyphosate for agricultural weed control, especially after Monsanto introduced glyphosate-resistant Roundup Ready crops, enabling farmers to kill weeds without killing their crops. In 2007, glyphosate was the most used herbicide in the United States' agricultural sector and the second-most used (after 2,4-D) in home and garden, government and industry, and commercial applications. From the late 1970s to 2016, there was a 100-fold increase in the frequency and volume of application of glyphosate-based herbicides (GBHs) worldwide, with further increases expected in the future. Glyphosate is absorbed through foliage, and minimally through roots, and from there translocated to growing points. It inhibits EPSP synthase, a plant enzyme involved in the synthesis of three aromatic amino acids: tyrosine, tryptophan, and phenylalanine. It is therefore effective only on actively growing plants and is not effective as a pre-emergence herbicide. Crops have been genetically engineered to be tolerant of glyphosate (e.g. Roundup Ready soybean, the first Roundup Ready crop, also created by Monsanto), which allows farmers to use glyphosate as a post-emergence herbicide against weeds. While glyphosate and formulations such as Roundup have been approved by regulatory bodies worldwide, concerns about their effects on humans and the environment have persisted. A number of regulatory and scholarly reviews have evaluated the relative toxicity of glyphosate as an herbicide. The WHO and FAO Joint committee on pesticide residues issued a report in 2016 stating the use of glyphosate formulations does not necessarily constitute a health risk, and giving an acceptable daily intake limit of 1 milligram per kilogram of body weight per day for chronic toxicity. The consensus among national pesticide regulatory agencies and scientific organizations is that labeled uses of glyphosate have demonstrated no evidence of human carcinogenicity. In March 2015, the World Health Organization's International Agency for Research on Cancer (IARC) classified glyphosate as "probably carcinogenic in humans" (category 2A) based on epidemiological studies, animal studies, and in vitro studies. In contrast, the European Food Safety Authority concluded in November 2015 that "the substance is unlikely to be genotoxic (i.e. damaging to DNA) or to pose a carcinogenic threat to humans", later clarifying that while carcinogenic glyphosate-containing formulations may exist, studies that "look solely at the active substance glyphosate do not show this effect". In 2017, the European Chemicals Agency (ECHA) classified glyphosate as causing serious eye damage and as toxic to aquatic life but did not find evidence implicating it as a carcinogen, a mutagen, toxic to reproduction, nor toxic to specific organs.
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Formula C3H8NO5P
Net Charge 0
Average Mass 169.07310
Monoisotopic Mass 169.01401
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
Brand Name Source
Roundup 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
Last Modified
21 June 2022