Identification

Name
Glyphosate
Accession Number
DB04539  (EXPT01639)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
4632WW1X5A
CAS number
1071-83-6
Weight
Average: 170.081
Monoisotopic: 170.021833915
Chemical Formula
C3H9NO5P
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-phosphoshikimate 1-carboxyvinyltransferase
inhibitor
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
U3-phosphoshikimate 1-carboxyvinyltransferaseNot AvailableEscherichia coli (strain K12)
UCytochrome P450 19A1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Glyphosate.Approved, Investigational
AmrinoneThe therapeutic efficacy of Glyphosate can be increased when used in combination with Amrinone.Approved
AzimilideThe therapeutic efficacy of Glyphosate can be increased when used in combination with Azimilide.Investigational
BuspironeThe metabolism of Buspirone can be decreased when combined with Glyphosate.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Glyphosate.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Glyphosate.Approved, Investigational, Withdrawn
DidanosineDidanosine can cause a decrease in the absorption of Glyphosate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Glyphosate.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Glyphosate.Approved
FosphenytoinThe serum concentration of Glyphosate can be decreased when it is combined with Fosphenytoin.Approved, Investigational
ProgesteroneThe absorption of Progesterone can be decreased when combined with Glyphosate.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Glyphosate.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Glyphosate.Approved, Investigational
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Glyphosate.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Glyphosate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Glyphosate.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Glyphosate.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Glyphosate.Approved, Investigational
Food Interactions
Not Available

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
External Links
KEGG Compound
C01705
PubChem Compound
5288464
PubChem Substance
46506916
ChemSpider
4450646
ChEBI
27744
Therapeutic Targets Database
DNC000698
HET
GPJ
Wikipedia
Glyphosate
PDB Entries
1g6s / 1rf6 / 2aay / 2gga / 2ggd / 2qft / 2qfu / 3nvs / 3slh

Clinical Trials

Clinical Trials
Not Available

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)6.34ChemAxon
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Alpha-amino acid or derivatives / Organophosphonic acid / Organophosphonic acid derivative / Amino acid / Carboxylic acid / Secondary aliphatic amine / Monocarboxylic acid or derivatives / Secondary amine / Organophosphorus compound / Organooxygen compound
show 10 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:15929894]

Carriers

Kind
Protein
Organism
Human
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. [PubMed:18035550]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 05:22