Basic Info

Common NameCarbaril(F03972)
2D Structure
Description

Carbaril is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

FRCD IDF03972
CAS Number63-25-2
PubChem CID6129
FormulaC12H11NO2
IUPAC Name

naphthalen-1-yl N-methylcarbamate

InChI Key

CVXBEEMKQHEXEN-UHFFFAOYSA-N

InChI

InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)

Canonical SMILES

CNC(=O)OC1=CC=CC2=CC=CC=C21

Isomeric SMILES

CNC(=O)OC1=CC=CC2=CC=CC=C21

Synonyms
        
            CARBARYL
        
            Carbaril
        
            63-25-2
        
            Sevin
        
            naphthalen-1-yl methylcarbamate
        
            1-Naphthyl N-methylcarbamate
        
            Caprolin
        
            Carbatox
        
            Carbavur
        
            Carylderm
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassNaphthalenes
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentNaphthalenes
Alternative Parents
Molecular FrameworkAromatic homopolycyclic compounds
SubstituentsNaphthalene - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homopolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Properties

Property NameProperty Value
Molecular Weight201.225
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity230
Monoisotopic Mass201.079
Exact Mass201.079
XLogP2.4
Formal Charge0
Heavy Atom Count15
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+0.9704
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7451
P-glycoprotein SubstrateNon-substrate0.7803
P-glycoprotein InhibitorNon-inhibitor0.8782
Non-inhibitor0.8382
Renal Organic Cation TransporterNon-inhibitor0.8520
Distribution
Subcellular localizationMitochondria0.5315
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7077
CYP450 2D6 SubstrateSubstrate0.8919
CYP450 3A4 SubstrateSubstrate0.5689
CYP450 1A2 InhibitorInhibitor0.8713
CYP450 2C9 InhibitorNon-inhibitor0.9167
CYP450 2D6 InhibitorNon-inhibitor0.8911
CYP450 2C19 InhibitorNon-inhibitor0.8167
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6550
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9097
Non-inhibitor0.9156
AMES ToxicityAMES toxic0.9107
CarcinogensNon-carcinogens0.9126
Fish ToxicityHigh FHMT0.9286
Tetrahymena Pyriformis ToxicityHigh TPT0.9907
Honey Bee ToxicityHigh HBT0.8439
BiodegradationNot ready biodegradable0.8678
Acute Oral ToxicityII0.7541
Carcinogenicity (Three-class)Warning0.5193

Model Value Unit
Absorption
Aqueous solubility-3.3427LogS
Caco-2 Permeability1.5334LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.9106LD50, mol/kg
Fish Toxicity1.0406pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5835pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Mace0870010European Union0.05*07/05/2015
Others (2)0870990European Union0.05*07/05/2015
Citrus fruits0110000European Union0.01*07/05/2015
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*07/05/2015
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*07/05/2015
Others (2)0110990European Union0.01*07/05/2015
Brazil nuts0120020European Union0.02*07/05/2015
Cashew nuts0120030European Union0.02*07/05/2015
Chestnuts0120040European Union0.02*07/05/2015
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*07/05/2015
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*07/05/2015
Macadamias0120070European Union0.02*07/05/2015
Pecans (Hickory nuts,)0120080European Union0.02*07/05/2015
Pistachios0120100European Union0.02*07/05/2015
Walnuts0120110European Union0.02*07/05/2015
Others (2)0120990European Union0.02*07/05/2015
Pome fruits0130000European Union0.01*07/05/2015
Apples (Crab apples/wild apples, Tejocotes,)0130010European Union0.01*07/05/2015
Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,)0130020European Union0.01*07/05/2015
Quinces (Chinese quinces, Japanese quinces,)0130030European Union0.01*07/05/2015

References

TitleJournalDatePubmed ID
Pharmaceuticals, hormones, pesticides, and other bioactive contaminants in water,sediment, and tissue from Rocky Mountain National Park, 2012-2013.Sci Total Environ2018 Jun 2629957431
An Amphibian with a Contracting Range Is Not More Vulnerable to Pesticides inOutdoor Experimental Communities Than Common Species.Environ Toxicol Chem2018 Jul 2330035389
Analytical Method for Pesticides in Avocado and Papaya by Means of Ultra-HighPerformance Liquid Chromatography Coupled to a Triple Quadrupole Mass Detector:Validation and Uncertainty Assessment.J Food Sci2018 Jul 1430007040
Development of a biomimetic enzyme-linked immunosorbent assay based onmolecularly imprinted polymers on paper for the detection of carbaryl.Food Chem2018 Feb 128946356
Nano carbon black-based screen printed sensor for carbofuran, isoprocarb,carbaryl and fenobucarb detection: application to grain samples.Talanta2018 Aug 1529784378
An integrated approach for assessing the migration behavior of chlorpyrifos andcarbaryl in the unsaturated soil zone.J Environ Sci Health B2018 Apr 6:1-729624471
Simultaneous Voltammetric Detection of Carbaryl and Paraquat Pesticides onGraphene-Modified Boron-Doped Diamond Electrode.Sensors (Basel)2017 Sep 628878151
Revealing Pesticide Residues Under High Pesticide Stress in Taiwan's AgriculturalEnvironment Probed by Fresh Honey Bee (Hymenoptera: Apidae) Pollen.J Econ Entomol2017 Oct 128981672
Comparison of Lindane and Carbaryl Pesticide Bioaccumulation in the Common Sole(Solea solea).Bull Environ Contam Toxicol2017 May28289805
Selection and Characterization of DNA Aptamers for Electrochemical Biosensing of Carbendazim.Anal Chem2017 Mar 728264568
Determination of a broad spectrum of endocrine-disrupting pesticides in fishsamples by UHPLC-MS/MS using the pass-through cleanup approach.J Sep Sci2017 Mar28098419
Aged garlic extract ameliorates immunotoxicity, hematotoxicity and impairedburn-healing in malathion- and carbaryl-treated male albino rats.Environ Toxicol2017 Mar27214522
Using Standing Gold Nanorod Arrays as Surface-Enhanced Raman Spectroscopy (SERS) Substrates for Detection of Carbaryl Residues in Fruit Juice and Milk.J Agric Food Chem2017 Jan 2528080039
Sex-dependent effects of developmental exposure to different pesticides onspatial learning. The role of induced neuroinflammation in the hippocampus.Food Chem Toxicol2017 Jan27908700
Inducible Tolerance to Agrochemicals Was Paved by Evolutionary Responses toPredators.Environ Sci Technol2017 Dec 529087697
Kinetic studies of the reaction between pesticides and hydroxyl radical generatedby laser flash photolysis.J Sci Food Agric2016 Mar 3025974279
Effects of washing, peeling, storage, and fermentation on residue contents ofcarbaryl and mancozeb in cucumbers grown in greenhouses.Toxicol Ind Health2016 Jun25342670
Brain acetylcholinesterase of jaguar cichlid (Parachromis managuensis): Fromphysicochemical and kinetic properties to its potential as biomarker ofpesticides and metal ions.Aquat Toxicol2016 Aug27288599
If you see one, have you seen them all?: Community-wide effects of insecticidecross-resistance in zooplankton populations near and far from agriculture.Environ Pollut2016 Aug27208756
Food safety in Thailand 2: Pesticide residues found in Chinese kale (Brassicaoleracea), a commonly consumed vegetable in Asian countries.Sci Total Environ2015 Nov 126093223

Targets

General Function:
Fatty acid amide hydrolase activity
Specific Function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:
FAAH
Uniprot ID:
O00519
Molecular Weight:
63065.28 Da
References
  1. Seierstad M, Breitenbucher JG: Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors. J Med Chem. 2008 Dec 11;51(23):7327-43. doi: 10.1021/jm800311k. [18983142 ]
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. Tarzia G, Duranti A, Tontini A, Piersanti G, Mor M, Rivara S, Plazzi PV, Park C, Kathuria S, Piomelli D: Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors. J Med Chem. 2003 Jun 5;46(12):2352-60. [12773040 ]
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
General Function:
Type iii transforming growth factor beta receptor binding
Specific Function:
Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
Gene Name:
TGFB1
Uniprot ID:
P01137
Molecular Weight:
44340.685 Da
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 ]
General Function:
Zinc ion binding
Specific Function:
Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
Gene Name:
MMP1
Uniprot ID:
P03956
Molecular Weight:
54006.61 Da
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 ]
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular Weight:
39759.945 Da
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 ]
General Function:
Primary amine oxidase activity
Specific Function:
Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and signal transduction. The VCAM1/ITGA4/ITGB1 interaction may play a pathophysiologic role both in immune responses and in leukocyte emigration to sites of inflammation.
Gene Name:
VCAM1
Uniprot ID:
P19320
Molecular Weight:
81275.43 Da
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 ]
General Function:
Sulfotransferase activity
Specific Function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular Weight:
33779.57 Da
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 ]
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
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 ]
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
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 ]
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
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 ]
General Function:
Cholesterol binding
Specific Function:
Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
Gene Name:
TSPO
Uniprot ID:
P30536
Molecular Weight:
18827.81 Da
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 ]
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
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 ]
General Function:
Ubiquitin protein ligase binding
Specific Function:
Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
Gene Name:
EGFR
Uniprot ID:
P00533
Molecular Weight:
134276.185 Da
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 ]
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
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 ]