Glyphosate

Basic Info

Common NameGlyphosate(F05876)
2D Structure
FRCD IDF05876
CAS Number1071-83-6
PubChem CID3496
FormulaC3H8NO5P
IUPAC Name

2-(phosphonomethylamino)acetic acid

InChI Key

XDDAORKBJWWYJS-UHFFFAOYSA-N

InChI

InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)

Canonical SMILES

C(C(=O)O)NCP(=O)(O)O

Isomeric SMILES

C(C(=O)O)NCP(=O)(O)O

Synonyms
        
            glyphosate
        
            1071-83-6
        
            N-(Phosphonomethyl)glycine
        
            Glyphosphate
        
            Roundup
        
            Glycine, N-(phosphonomethyl)-
        
            Pondmaster
        
            Silglif
        
            Roundup Max
        
            2-(phosphonomethylamino)acetic acid
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsAlpha-amino acid or derivatives - Organophosphonic acid - Organophosphonic acid derivative - Amino acid - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Secondary amine - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organophosphorus compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Amine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Properties

Property NameProperty Value
Molecular Weight169.073
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Complexity162
Monoisotopic Mass169.014
Exact Mass169.014
XLogP-4.6
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.6217
Human Intestinal AbsorptionHIA-0.9571
Caco-2 PermeabilityCaco2-0.6921
P-glycoprotein SubstrateNon-substrate0.6474
P-glycoprotein InhibitorNon-inhibitor0.9502
Non-inhibitor0.9857
Renal Organic Cation TransporterNon-inhibitor0.9540
Distribution
Subcellular localizationMitochondria0.6329
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8166
CYP450 2D6 SubstrateNon-substrate0.8284
CYP450 3A4 SubstrateNon-substrate0.7249
CYP450 1A2 InhibitorNon-inhibitor0.9046
CYP450 2C9 InhibitorNon-inhibitor0.9096
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8358
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9856
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7582
Non-inhibitor0.9233
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.6623
Fish ToxicityHigh FHMT0.6278
Tetrahymena Pyriformis ToxicityLow TPT0.9558
Honey Bee ToxicityLow HBT0.5734
BiodegradationReady biodegradable0.7392
Acute Oral ToxicityIII0.7679
Carcinogenicity (Three-class)Non-required0.6419
Model Value Unit
Absorption
Aqueous solubility-0.8178LogS
Caco-2 Permeability-0.9867LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5712LD50, mol/kg
Fish Toxicity2.2860pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.5679pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.1*06/04/2013
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.1*06/04/2013
Azaroles/Mediterranean medlars0154070European Union0.1*06/04/2013
Elderberries (Bayberries, Buffalo berries, Che berries, Dwarf elderberries, Guelder rose berries, Hawberries, Midland hawberries, Phalsa fruits, Riberries, Rowan berries, Saskatoons/saskatoons berr...0154080European Union0.1*06/04/2013
Salsifies (Burdocks, Rampion roots, Scorzonera/black salsifies, Skirrets, Spanish salsifies,)0213090European Union0.1*06/04/2013
Tomatoes (Alkekengi/Chinese lanterns/ground cherries, Cape gooseberries, Cherry tomatoes, Dwarf Cape gooseberries/strawberry tomatoes, Gojiberries/wolfberries, Gojiberries/wolfberries, Litchi tomat...0231010European Union0.1*06/04/2013
Baby leaf crops (including brassica species) (Chards/beet leaves, Escaroles/broad-leaved endives, Indian mustards/mustard greens, Lettuces, Spinaches, Other species harvested at baby leaf stage,)0251080European Union0.1*06/04/2013
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.506/04/2013
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.1*06/04/2013
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.1*06/04/2013
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.506/04/2013
Others (2)0110990European Union0.1*06/04/2013
Tree nuts0120000European Union0.1*06/04/2013
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.1*06/04/2013
Brazil nuts0120020European Union0.1*06/04/2013
Cashew nuts0120030European Union0.1*06/04/2013
Chestnuts0120040European Union0.1*06/04/2013
Coconuts (Areca nuts/betel nuts,)0120050European Union0.1*06/04/2013
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.1*06/04/2013
Macadamias0120070European Union0.1*06/04/2013

References

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The Ramazzini Institute 13-week study on glyphosate-based herbicides athuman-equivalent dose in Sprague Dawley rats: study design and first in-lifeendpoints evaluation.Environ Health2018 May 2929843719
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Validation and application of analytical method for glyphosate and glufosinate infoods by liquid chromatography-tandem mass spectrometry.J Chromatogr A2018 May 1129588098
Six months exposure to a real life mixture of 13 chemicals' below individualNOAELs induced non monotonic sex-dependent biochemical and redox status changesin rats.Food Chem Toxicol2018 May29621577
Environmental and health effects of the herbicide glyphosate.Sci Total Environ2018 Mar29117584
Transgene escape and persistence in an agroecosystem: the case ofglyphosate-resistant Brassica rapa L. in central Argentina.Environ Sci Pollut Res Int2018 Mar29243152
Contact with a glyphosate-based herbicide has long-term effects on the activityand foraging of an agrobiont wolf spider.Chemosphere2018 Mar29247931
Confronting herbicide resistance with cooperative management.Pest Manag Sci2018 Jun 329862629
Ecotoxicological effects of the herbicide glyphosate in non-target aquaticspecies: Transcriptional responses in the mussel Mytilus galloprovincialis.Environ Pollut2018 Jun29505984
Influence of microplastic addition on glyphosate decay and soil microbialactivities in Chinese loess soil.Environ Pollut2018 Jul 329990941
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The mechanism of DNA damage induced by Roundup 360 PLUS, glyphosate and AMPA inhuman peripheral blood mononuclear cells - genotoxic risk assessement.Food Chem Toxicol2018 Jul 2530055318
The Herbicide Glyphosate Negatively Affects Midgut Bacterial Communities andSurvival of Honey Bee during Larvae Reared in Vitro.J Agric Food Chem2018 Jul 2529992812
An Amphibian with a Contracting Range Is Not More Vulnerable to Pesticides inOutdoor Experimental Communities Than Common Species.Environ Toxicol Chem2018 Jul 2330035389
Weeds and ground-dwelling predators' response to two different weed managementsystems in glyphosate-tolerant cotton: A farm-scale study.PLoS One2018 Jan 1929351549
Nanosensing of Pesticides by Zinc Oxide Quantum Dot: An Optical andElectrochemical Approach for the Detection of Pesticides in Water.J Agric Food Chem2018 Jan 1729239610
Glyphosate analysis using sensors and electromigration separation techniques asalternatives to gas or liquid chromatography.Anal Bioanal Chem2018 Jan29098335