(±)-Metalaxyl
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Basic Info
| Common Name | (±)-Metalaxyl(F04085) |
| 2D Structure | |
| Description | (±)-Metalaxyl is a systemic agricultural fungicide belonging to the family of Depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually I-amino and I-hydroxy acids), commonly but not necessarily regularly alternating. |
| FRCD ID | F04085 |
| CAS Number | 57837-19-1 |
| PubChem CID | 42586 |
| Formula | C15H21NO4 |
| IUPAC Name | methyl 2-(N-(2-methoxyacetyl)-2,6-dimethylanilino)propanoate |
| InChI Key | ZQEIXNIJLIKNTD-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3 |
| Canonical SMILES | CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC |
| Isomeric SMILES | CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC |
| Synonyms |
METALAXYL
57837-19-1
Ridomil
Allegiance
Metanaxin
Metasyl
Apron
Jiashuangling
Metalaxil
Metaxanin
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Alpha amino acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Alpha-amino acid ester - Alanine or derivatives - Anilide - M-xylene - Xylene - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Methyl ester - Carboxylic acid ester - Carboxamide group - Monocarboxylic acid or derivatives - Ether - Dialkyl ether - Organopnictogen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 279.336 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Complexity | 335 |
| Monoisotopic Mass | 279.147 |
| Exact Mass | 279.147 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9505 |
| Human Intestinal Absorption | HIA+ | 0.8096 |
| Caco-2 Permeability | Caco2+ | 0.6354 |
| P-glycoprotein Substrate | Non-substrate | 0.7580 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7157 |
| Non-inhibitor | 0.6135 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8969 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7228 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7957 |
| CYP450 2D6 Substrate | Non-substrate | 0.8077 |
| CYP450 3A4 Substrate | Substrate | 0.6675 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7646 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7594 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9333 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6393 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9049 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6610 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9914 |
| Non-inhibitor | 0.9065 | |
| AMES Toxicity | Non AMES toxic | 0.6961 |
| Carcinogens | Non-carcinogens | 0.7370 |
| Fish Toxicity | Low FHMT | 0.6740 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7171 |
| Honey Bee Toxicity | Low HBT | 0.8755 |
| Biodegradation | Not ready biodegradable | 0.7221 |
| Acute Oral Toxicity | III | 0.7911 |
| Carcinogenicity (Three-class) | Non-required | 0.6351 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.6620 | LogS |
| Caco-2 Permeability | 1.1367 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6617 | LD50, mol/kg |
| Fish Toxicity | 1.0404 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0837 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Reduction of pesticide residues from tomatoes by low intensity electrical currentand ultrasound applications. | Food Chem | 2018 Nov 30 | 29934190 |
| Metalaxyl Effects on Antioxidant Defenses in Leaves and Roots of Solanum nigrumL. | Front Plant Sci | 2017 Nov 30 | 29250085 |
| Acylamino acid chiral fungicides on toxiciepigenetics in lambda DNA methylation. | Food Chem Toxicol | 2017 Nov | 28456568 |
| Enantioselective Effects of Metalaxyl Enantiomers on Breast Cancer CellsMetabolic Profiling Using HPLC-QTOF-Based Metabolomics. | Int J Mol Sci | 2017 Jan 12 | 28085117 |
| Food safety in Thailand. 3: Pesticide residues detected in mangosteen (Garciniamangostana L.), queen of fruits. | J Sci Food Agric | 2017 Feb | 27185538 |
| Simultaneous removal of structurally different pesticides in a biomixture:Detoxification and effect of oxytetracycline. | Chemosphere | 2017 Feb | 27898329 |
| Effect of processing on the disappearance of pesticide residues in fresh-cutlettuce: Bioavailability and dietary risk. | J Environ Sci Health B | 2017 Dec 2 | 28949798 |
| Degradation Processes of Pesticides Used in Potato Cultivations. | Rev Environ Contam Toxicol | 2017 | 27718007 |
| Enantioselective metabolism and toxic effects of metalaxyl on primary hepatocytes from rat. | Environ Sci Pollut Res Int | 2016 Sep | 27306210 |
| Cultivating Chlorella vulgaris and Scenedesmus quadricauda microalgae to degrade inorganic compounds and pesticides in water. | Environ Sci Pollut Res Int | 2016 Sep | 27259964 |
| Evaluation of an organo-layered double hydroxide and two organic residues asamendments to immobilize metalaxyl enantiomers in soils: A comparative study. | J Environ Manage | 2016 Oct 1 | 27341374 |
| Food safety in Thailand 2: Pesticide residues found in Chinese kale (Brassicaoleracea), a commonly consumed vegetable in Asian countries. | Sci Total Environ | 2015 Nov 1 | 26093223 |
| Food safety in Thailand 1: it is safe to eat watermelon and durian in Thailand. | Environ Health Prev Med | 2015 May | 25697579 |
| Pesticide and trace metal occurrence and aquatic benchmark exceedances in surfacewaters and sediments of urban wetlands and retention ponds in Melbourne,Australia. | Environ Sci Pollut Res Int | 2015 Jul | 25697552 |
| Rapid metabolite discovery, identification, and accurate comparison of thestereoselective metabolism of metalaxyl in rat hepatic microsomes. | J Agric Food Chem | 2015 Jan 28 | 25581548 |
| Development, validation and determination of multiclass pesticide residues incocoa beans using gas chromatography and liquid chromatography tandem massspectrometry. | Food Chem | 2015 Apr 1 | 25442595 |
| Dissipation behaviour, processing factors and risk assessment for metalaxyl ingreenhouse-grown cucumber. | Pest Manag Sci | 2015 Apr | 25044468 |
| Determination of fungicides in white grape bagasse by pressurized liquidextraction and gas chromatography tandem mass spectrometry. | J Chromatogr A | 2014 May 23 | 24746069 |
| Analysis of 10 systemic pesticide residues in various baby foods using liquidchromatography-tandem mass spectrometry. | Biomed Chromatogr | 2014 Jun | 24861738 |
| Analytical approaches for the determination of pesticide residues innutraceutical products and related matrices by chromatographic techniques coupledto mass spectrometry. | Talanta | 2014 Jan | 24274299 |
Targets
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB4
- Uniprot ID:
- P30926
- Molecular Weight:
- 56378.985 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Receptor binding
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
- Gene Name:
- CHRNA10
- Uniprot ID:
- Q9GZZ6
- Molecular Weight:
- 49704.295 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA3
- Uniprot ID:
- P32297
- Molecular Weight:
- 57479.54 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
- Gene Name:
- CHRNA4
- Uniprot ID:
- P43681
- Molecular Weight:
- 69956.47 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Toxic substance binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
- Gene Name:
- CHRNA7
- Uniprot ID:
- P36544
- Molecular Weight:
- 56448.925 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Calcium channel activity
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
- Gene Name:
- CHRNA9
- Uniprot ID:
- Q9UGM1
- Molecular Weight:
- 54806.63 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
- Gene Name:
- CHRNB2
- Uniprot ID:
- P17787
- Molecular Weight:
- 57018.575 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB3
- Uniprot ID:
- Q05901
- Molecular Weight:
- 52728.215 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- 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:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular Weight:
- 76447.99 Da
References
- 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:
- 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
References
- 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
- 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:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA5
- Uniprot ID:
- P30532
- Molecular Weight:
- 53053.965 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- General Function:
- Acetylcholine-activated cation-selective channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA6
- Uniprot ID:
- Q15825
- Molecular Weight:
- 56897.745 Da
- Mechanism of Action:
- Binds to nAChRs in nervous systems.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- 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
- 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 ]