Guthion (T3D0135)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (14)XML
Targets (14)
Record Information
Version2.0
Creation Date2009-03-06 18:58:08 UTC
Update Date2014-12-24 20:21:11 UTC
Accession NumberT3D0135
Identification
Common NameGuthion
ClassSmall Molecule
DescriptionGuthion, also called azinphos-methyl, is a synthetic organophosphorous pesticide. It has been used on many different crops, especially apples, pears, cherries, peaches, almonds, and cotton. Due to its toxicity, its use has been banned or tightly regulated in most areas today. (4)
Compound Type
  • Ester
  • Food Toxin
  • Organic Compound
  • Organophosphate
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioate
Azimil
Azinfos-methyl
Azinophos-methyl
Azinphos
Azinphos methyl
Azinphos methyl mixture
Azinphos-me
Azinphos-metile
Azinphosmethyl
Beetle buster
Benzotriazinedithiophosphoric acid dimethoxy ester
Carfene
Cotneon
Cotnion
Cotnion methyl
Crysthyon
Dimethyl dithiophosphoric acid N-methylbenzazimidyl ester
Dimethyldithiophosphoric acid N-methylbenzazimide ester
Go thnion
Gothnion
Gusathion
Gusathion methyl
Gusthion m
Guthion (azinphos-methyl)
Guthion mixture
Guthion(r)
Guthion, gusation
Gution
Metazintox
Methyl azinphos
Methyl gusathion
Methyl guthion
Methylazinphos
Methylgusathion
Methyltriazotin
Metiltriazotion
N-Methylbenzazimide, dimethyl dithiophosphoric acid ester
N-methylbenzazimide, dimethyldithiophosphoric acid ester
Nitrinal
O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate
O,O-dimethyl S-(be nzaziminomethyl) dithiophosphate
O,O-dimethyl S-(benzaziminomethyl) dithiophosphate
O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphate
O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat
O,O-dimethyl-s-(benzaziminomethyl) dithiophosphate
Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester
Zinphos methyl
Chemical FormulaC10H12N3O3PS2
Average Molecular Mass317.324 g/mol
Monoisotopic Mass317.006 g/mol
CAS Registry Number86-50-0
IUPAC NameO,O-dimethyl {[(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)methyl]sulfanyl}phosphonothioate
Traditional NameO,O-dimethyl [(4-oxo-1,2,3-benzotriazin-3-yl)methyl]sulfanylphosphonothioate
SMILESCOP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O
InChI IdentifierInChI=1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3
InChI KeyInChIKey=CJJOSEISRRTUQB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzotriazine organothiophosphates. These are aromatic compounds containing a benzo-1,2,3-triazine, which is substituted by an organothiophosphate group at the 3-position. Their general structure is R-CSP(=S)(OR')OR'', where R=benzo-1,2,3-triazine, R',R\" = any atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzo-1,2,3-triazines
Sub ClassBenzotriazine organothiophosphates
Direct ParentBenzotriazine organothiophosphates
Alternative Parents
Substituents
  • Benzotriazine organothiophosphate
  • Triazinone
  • Triazine
  • Dithiophosphate s-ester
  • Benzenoid
  • 1,2,3-triazine
  • Dithiophosphate o-ester
  • Heteroaromatic compound
  • Organic dithiophosphate
  • Lactam
  • Azacycle
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceColorless to white crystals.
Experimental Properties
PropertyValue
Melting Point73°C
Boiling PointNot Available
Solubility0.0209 mg/mL at 20 °C [BOWMAN,BT & SANS,WW (1983)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP2.75ALOGPS
logP3.24ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.49 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.64 m³·mol⁻¹ChemAxon
Polarizability29.62 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-0910000000-8a90862fb34d7f1de4d62021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-008c-0900000000-c3d2041851aea43793d82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-d45bfd942d49cb4291ae2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0kdj-9300000000-8aab23fdf429810129832021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-008c-0900000000-1af926d96f15ea4fe0292021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0kdm-9600000000-87f03e4a5118de93472b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-65ca1a571d6e6181a0882021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-c34b6732021b15900ca62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-7cfe94f327d288d4482c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-56fb2b538788f6a5dd632021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000x-0900000000-02de58086414fbca0a4b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000x-1900000000-eacce6bcbada6302fcfb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-03ec-0910000000-4f5411792d4477abc5882021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-1900000000-0d479bb903e25e1f854e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0kbg-5900000000-3e0b563fe56090b9433a2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0119000000-6b01cea6b4efafb87ffc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-2c07ac5163df5ab1dc152016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-4a556662783ce60fac922016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0902000000-8064bfc10805102a22bc2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-e2f755731cfbdd47a5622021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-e63b011d200285b09caa2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-0639000000-d7afc7588998311cc61f2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-6908000000-2adf23de316e0ef841d42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-6900000000-ab0ac3300b9628fd5fa42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-c86324755309401cbaea2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-558e5a824d096c6201922021-10-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0in9-8900000000-dcab6b11e3ab3e51c6c82014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; dermal (4) ; inhalation (4)
Mechanism of ToxicityGuthion is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesLD50: 11 mg/kg (Oral, Rat) (2) LD50: 4900 ug/kg (Intraperitoneal, Rat) (1) LD50: 7500 ug/kg (Intravenous, Rat) (1) LD50: 65 mg/kg (Dermal, Mouse) (1) LC50: 0.15 mg/L over 4 hours (Inhalation, Rat) (2)
Lethal Dose5 to 50 mg/kg for an adult human. (5)
Carcinogenicity (IARC Classification)Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (6)
Uses/SourcesGuthion is used as a pesticide, thus exposure usually occurs from eating contaminated food. (4)
Minimum Risk LevelAcute Inhalation: 0.02 mg/m3 (3) Intermediate Inhalation: 0.01 mg/m3 (3) Chronic Inhalation: 0.01 mg/m3 (3) Acute Oral: 0.01 mg/kg/day (3) Intermediate Oral: 0.003 mg/kg/day (3) Chronic Oral: mg/kg/day (3)
Health EffectsAcute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
SymptomsGuthion interferes with the nerves and brain normal way. Exposure to very high levels of guthion for a short period in air, water, or food may cause difficulty breathing, chest tightness, vomiting, cramps, diarrhea, blurred vision, sweating, headaches, dizziness, loss of consciousness, and death. (4)
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID2268
ChEMBL IDCHEMBL530115
ChemSpider ID2181
KEGG IDC11018
UniProt IDNot Available
OMIM ID
ChEBI ID2953
BioCyc IDNot Available
CTD IDD001387
Stitch IDGuthion
PDB IDNot Available
ACToR ID123
Wikipedia LinkAzinphos-methyl
References
Synthesis ReferenceNot Available
MSDST3D0135.pdf
General References
  1. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  2. Tomlin CDS (ed) (2002). Azinphos methyl (86-50-0). In: The e-Pesticide Manual, Version 2.2. Surrey UK: British Crop Protection Council.
  3. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (1990). Toxicological profile for guthion. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. International Programme on Chemical Safety (IPCS) INCHEM (2009). Pesticide Document for Azinphos-methyl. [Link]
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Acetylcholinesterase
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1990). Toxicological profile for guthion. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Target Details
2. Cytochrome P450 2C19
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.16 uMNVS_ADME_hCYP2C19Novascreen
AC500.21 uMNVS_ADME_hCYP2C19Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
3. Cytochrome P450 2B6
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.28 uMNVS_ADME_hCYP2B6Novascreen
AC500.53 uMCLZD_CYP2B6_6CellzDirect
AC509.87 uMCLZD_CYP2B6_24CellzDirect
AC509.93 uMCLZD_CYP2B6_48CellzDirect
AC500.28 uMNVS_ADME_hCYP2B6Novascreen
AC500.53 uMCLZD_CYP2B6_6CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
4. Cytochrome P450 1A1
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.33 uMNVS_ADME_hCYP1A1Novascreen
AC505.11 uMCLZD_CYP1A1_24CellzDirect
AC506.16 uMCLZD_CYP1A1_48CellzDirect
AC500.36 uMNVS_ADME_hCYP1A1Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
5. Cytochrome P450 3A4
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.49 uMCLZD_CYP3A4_6CellzDirect
AC507.13 uMCLZD_CYP3A4_24CellzDirect
AC506.12 uMCLZD_CYP3A4_48CellzDirect
AC500.49 uMCLZD_CYP3A4_6CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
6. Cytochrome P450 2J2
General Function:
Steroid hydroxylase activity
Specific Function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular Weight:
57610.165 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.54 uMNVS_ADME_hCYP2J2Novascreen
AC503.30 uMNVS_ADME_hCYP2J2Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
7. Cytochrome P450 1A2
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.12 uMNVS_ADME_hCYP1A2Novascreen
AC507.15 uMCLZD_CYP1A2_24CellzDirect
AC501.19 uMCLZD_CYP1A2_48CellzDirect
AC506.00 uMNVS_ADME_hCYP1A2Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
8. Cytochrome P450 2C18
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.55 uMNVS_ADME_hCYP2C18Novascreen
AC502.10 uMNVS_ADME_hCYP2C18Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
9. Cytochrome P450 3A5
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.04 uMNVS_ADME_hCYP3A5Novascreen
AC503.10 uMNVS_ADME_hCYP3A5Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
10. UDP-glucuronosyltransferase 1-1
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.68 uMCLZD_UGT1A1_6CellzDirect
AC509.73 uMCLZD_UGT1A1_24CellzDirect
AC508.65 uMCLZD_UGT1A1_48CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
11. Cytochrome P450 2C9
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.32 uMNVS_ADME_hCYP2C9Novascreen
AC5010.00 uMNVS_ADME_hCYP2C9Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
12. Cytochrome P450 2D6
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.37 uMNVS_ADME_hCYP2D6Novascreen
AC509.80 uMNVS_ADME_hCYP2D6Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
13. Tissue factor
General Function:
Protease binding
Specific Function:
Initiates blood coagulation by forming a complex with circulating factor VII or VIIa. The [TF:VIIa] complex activates factors IX or X by specific limited protolysis. TF plays a role in normal hemostasis by initiating the cell-surface assembly and propagation of the coagulation protease cascade.
Gene Name:
F3
Uniprot ID:
P13726
Molecular Weight:
33067.3 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.44 uMBSK_3C_TissueFactor_downBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
14. P2Y purinoceptor 1
General Function:
Scaffold protein binding
Specific Function:
Receptor for extracellular adenine nucleotides such as ATP and ADP. In platelets binding to ADP leads to mobilization of intracellular calcium ions via activation of phospholipase C, a change in platelet shape, and probably to platelet aggregation.
Gene Name:
P2RY1
Uniprot ID:
P47900
Molecular Weight:
42071.08 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.77 uMNVS_GPCR_hPY2Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]