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Identification
NameGlyphosate
Accession NumberDB04539  (EXPT01639)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII4632WW1X5A
CAS number1071-83-6
WeightAverage: 170.081
Monoisotopic: 170.021833915
Chemical FormulaC3H9NO5P
InChI KeyInChIKey=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
Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Quaternary ammonium salt
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point189.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24