Glyphosate

Identification

Generic Name
Glyphosate
DrugBank Accession Number
DB04539
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 170.081
Monoisotopic: 170.021833915
Chemical Formula
C3H9NO5P
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCytochrome P450 19A1Not AvailableHumans
U3-phosphoshikimate 1-carboxyvinyltransferaseNot AvailableEscherichia coli (strain K12)
U3-phosphoshikimate 1-carboxyvinyltransferase
inhibitor
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Organic phosphonic acids / Amino acids / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Organopnictogen compounds / Organophosphorus compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Aliphatic acyclic compound / Alpha-amino acid or derivatives / Amine / Amino acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic cation / Organic nitrogen compound
show 10 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
4632WW1X5A
CAS number
1071-83-6
InChI Key
XDDAORKBJWWYJS-UHFFFAOYSA-O
InChI
InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)/p+1
IUPAC Name
(carboxymethyl)(phosphonomethyl)azanium
SMILES
OC(=O)C[NH2+]CP(O)(O)=O

References

Synthesis Reference

Donald L. Fields, Jr., Len F. Lee, Thomas J. Richard, "Process for making glyphosate from n-phosphonomethyl-2-oxazolidone." U.S. Patent US4810426, issued November, 1966.

US4810426
General References
Not Available
KEGG Compound
C01705
PubChem Compound
5288464
PubChem Substance
46506916
ChemSpider
4450646
RxNav
1800093
ChEBI
27744
Therapeutic Targets Database
DNC000698
PDBe Ligand
GPJ
Wikipedia
Glyphosate
PDB Entries
1g6s / 1rf6 / 2aay / 2gga / 2ggd / 2qft / 2qfu / 3slh / 7f7m / 7tm6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)189.5 °CPhysProp
water solubility1.2E+004 mg/L (at 25 °C)WORTHING,CR & WALKER,SB (1987)
logP-4.00DAYLIGHT (1999)
pKa0.8TOMLIN,C (1997); pKa1
Predicted Properties
PropertyValueSource
Water Solubility10.7 mg/mLALOGPS
logP0.04ALOGPS
logP-3.1Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)-0.58Chemaxon
pKa (Strongest Basic)9.56Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area111.44 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity42.77 m3·mol-1Chemaxon
Polarizability13.37 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9956
Blood Brain Barrier+0.5739
Caco-2 permeable-0.6816
P-glycoprotein substrateNon-substrate0.655
P-glycoprotein inhibitor INon-inhibitor0.9747
P-glycoprotein inhibitor IINon-inhibitor0.9903
Renal organic cation transporterNon-inhibitor0.9596
CYP450 2C9 substrateNon-substrate0.8581
CYP450 2D6 substrateNon-substrate0.8221
CYP450 3A4 substrateNon-substrate0.7315
CYP450 1A2 substrateNon-inhibitor0.8677
CYP450 2C9 inhibitorNon-inhibitor0.8942
CYP450 2D6 inhibitorNon-inhibitor0.8993
CYP450 2C19 inhibitorNon-inhibitor0.8726
CYP450 3A4 inhibitorNon-inhibitor0.8383
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9902
Ames testNon AMES toxic0.8675
CarcinogenicityNon-carcinogens0.6755
BiodegradationReady biodegradable0.9055
Rat acute toxicity1.6553 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8196
hERG inhibition (predictor II)Non-inhibitor0.9169
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-007x-9300000000-8463a1d5c1211c7c502b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-117.497696
predicted
DeepCCS 1.0 (2019)
[M+H]+121.364784
predicted
DeepCCS 1.0 (2019)
[M+Na]+130.2568
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Richard S, Moslemi S, Sipahutar H, Benachour N, Seralini GE: Differential effects of glyphosate and roundup on human placental cells and aromatase. Environ Health Perspect. 2005 Jun;113(6):716-20. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
3-phosphoshikimate 1-carboxyvinyltransferase activity
Specific Function
Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name
aroA
Uniprot ID
P0A6D3
Uniprot Name
3-phosphoshikimate 1-carboxyvinyltransferase
Molecular Weight
46095.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
3-phosphoshikimate 1-carboxyvinyltransferase activity
Specific Function
Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name
aroA
Uniprot ID
Q9S400
Uniprot Name
3-phosphoshikimate 1-carboxyvinyltransferase
Molecular Weight
45765.42 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Yue Y, Zhang Y, Zhou L, Qin J, Chen X: In vitro study on the binding of herbicide glyphosate to human serum albumin by optical spectroscopy and molecular modeling. J Photochem Photobiol B. 2008 Jan 30;90(1):26-32. Epub 2007 Oct 18. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52