(±)-Naled
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Basic Info
| Common Name | (±)-Naled(F03447) |
| 2D Structure | |
| Description | (±)-Naled is an Agricultural insecticide, acaricide, bactericide and fungicide (±)-Naled belongs to the family of Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. |
| FRCD ID | F03447 |
| CAS Number | 300-76-5 |
| PubChem CID | 4420 |
| Formula | C4H7Br2Cl2O4P |
| IUPAC Name | (1,2-dibromo-2,2-dichloroethyl) dimethyl phosphate |
| InChI Key | BUYMVQAILCEWRR-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3 |
| Canonical SMILES | COP(=O)(OC)OC(C(Cl)(Cl)Br)Br |
| Isomeric SMILES | COP(=O)(OC)OC(C(Cl)(Cl)Br)Br |
| Synonyms |
Bromchlophos
naled
Dibrom
Bromex
300-76-5
Ortho-Dibrom
Dibromfos
Alvora
Fosbrom
Flibol Ex
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic phosphoric acids and derivatives |
| Subclass | Phosphate esters |
| Intermediate Tree Nodes | Alkyl phosphates |
| Direct Parent | Trialkyl phosphates |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Trialkyl phosphate - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organobromide - Organohalogen compound - Alkyl halide - Alkyl chloride - Alkyl bromide - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 380.778 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 206 |
| Monoisotopic Mass | 377.783 |
| Exact Mass | 379.781 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.9708 |
| Human Intestinal Absorption | HIA+ | 0.9791 |
| Caco-2 Permeability | Caco2- | 0.5869 |
| P-glycoprotein Substrate | Non-substrate | 0.8707 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9391 |
| Non-inhibitor | 0.9696 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9453 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7534 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8167 |
| CYP450 2D6 Substrate | Non-substrate | 0.8336 |
| CYP450 3A4 Substrate | Non-substrate | 0.5419 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8355 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8683 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9294 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6723 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9514 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9123 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9361 |
| Non-inhibitor | 0.9277 | |
| AMES Toxicity | AMES toxic | 0.8715 |
| Carcinogens | Carcinogens | 0.7534 |
| Fish Toxicity | High FHMT | 0.5578 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8129 |
| Honey Bee Toxicity | High HBT | 0.9166 |
| Biodegradation | Not ready biodegradable | 0.9558 |
| Acute Oral Toxicity | II | 0.6488 |
| Carcinogenicity (Three-class) | Non-required | 0.5353 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2178 | LogS |
| Caco-2 Permeability | 0.3800 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.6482 | LD50, mol/kg |
| Fish Toxicity | 1.2903 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2317 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Cotton Seed | Australia | 0.02mg/kg | |||
| Beans | Canada | 0. 5mg/kg | |||
| Vegetable | New Zealand | 2mg/kg | |||
| Brussels Sprouts | Canada | 1mg/kg | |||
| Cabbages | Canada | 1mg/kg | |||
| Cauliflower | Canada | 1mg/kg | |||
| Chard | Canada | 3mg/kg | |||
| Citrus Fruits | Canada | 3mg/kg | |||
| Cucumbers | Canada | 0. 5mg/kg | |||
| Lettuce | Canada | 1mg/kg | |||
| Melons | Canada | 0. 5mg/kg | |||
| Peas | Canada | 0. 5mg/kg | |||
| Peppers | Canada | 0. 5mg/kg | |||
| Pumpkins | Canada | 0. 5mg/kg | |||
| Rice | Canada | 0. 5mg/kg | |||
| Soybeans | Canada | 0. 5mg/kg | |||
| Spinach | Canada | 3mg/kg | |||
| Squash | Canada | 0. 5mg/kg | |||
| Strawberries | Canada | 1mg/kg | |||
| Tomatoes | Canada | 0. 5mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Community air monitoring for pesticides-part 2: multiresidue determination ofpesticides in air by gas chromatography, gas chromatography-mass spectrometry,and liquid chromatography-mass spectrometry. | Environ Monit Assess | 2014 Mar | 24370860 |
| Glove accumulation of pesticide residues for strawberry harvester exposureassessment. | Bull Environ Contam Toxicol | 2011 Jun | 21503692 |
| Evaluation of SPLAT with spinosad and methyl eugenol or cue-lure for"attract-and-kill" of oriental and melon fruit flies (Diptera: Tephritidae) inHawaii. | J Econ Entomol | 2008 Jun | 18613576 |
| Minimizing the impact of the mosquito adulticide naled on honey bees, Apismellifera (Hymenoptera: Apidae): aerial ultra-low-volume application using ahigh-pressure nozzle system. | J Econ Entomol | 2004 Feb | 14998120 |
| Impact of naled on honey bee Apis mellifera L. survival and productivity: aerial ULV application using a flat-fan nozzle system. | Arch Environ Contam Toxicol | 2003 Aug | 14565579 |
| Effects of ultra-low volume and thermal fog malathion, Scourge and naled applied against caged adult Culicoides furens and Culex quinquefasciatus in open andvegetated terrain. | J Am Mosq Control Assoc | 1992 Mar | 1583493 |
| Evaluation of ULV naled applied simultaneously against caged adult Aedestaeniorhynchus and Culicoides furens. | J Am Mosq Control Assoc | 1988 Sep | 3199122 |
| Use of the insecticide naled to control zearalenone production. | J Agric Food Chem | 1976 Sep-Oct | 965609 |
Targets
- General Function:
- Cytokine activity
- Specific Function:
- Cytokine that affects the growth, movement, or activation state of cells that participate in immune and inflammatory response. Chemotactic for activated T-cells. Binds to CXCR3.
- Gene Name:
- CXCL9
- Uniprot ID:
- Q07325
- Molecular Weight:
- 14018.72 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:
- 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
- Wani WY, Gudup S, Sunkaria A, Bal A, Singh PP, Kandimalla RJ, Sharma DR, Gill KD: Protective efficacy of mitochondrial targeted antioxidant MitoQ against dichlorvos induced oxidative stress and cell death in rat brain. Neuropharmacology. 2011 Dec;61(8):1193-201. doi: 10.1016/j.neuropharm.2011.07.008. Epub 2011 Jul 26. [21784090 ]
- 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
References
- Soininen H, Unni L, Shillcutt S: Effect of acute and chronic cholinesterase inhibition on biogenic amines in rat brain. Neurochem Res. 1990 Dec;15(12):1185-90. [1711162 ]
- 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
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:
- 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
- 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:
- Glutathione transferase activity
- Specific Function:
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
- Gene Name:
- GSTA2
- Uniprot ID:
- P09210
- Molecular Weight:
- 25663.675 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:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 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:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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:
- 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
- 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:
- Protein homodimerization activity
- Specific Function:
- Cytokine that plays an essential role in the regulation of survival, proliferation and differentiation of hematopoietic precursor cells, especially mononuclear phagocytes, such as macrophages and monocytes. Promotes the release of proinflammatory chemokines, and thereby plays an important role in innate immunity and in inflammatory processes. Plays an important role in the regulation of osteoclast proliferation and differentiation, the regulation of bone resorption, and is required for normal bone development. Required for normal male and female fertility. Promotes reorganization of the actin cytoskeleton, regulates formation of membrane ruffles, cell adhesion and cell migration. Plays a role in lipoprotein clearance.
- Gene Name:
- CSF1
- Uniprot ID:
- P09603
- Molecular Weight:
- 60178.885 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 ]