Chlorpropham
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Basic Info
| Common Name | Chlorpropham(F03981) |
| 2D Structure | |
| Description | Chlorpropham 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 ID | F03981 |
| CAS Number | 101-21-3 |
| PubChem CID | 2728 |
| Formula | C10H12ClNO2 |
| IUPAC Name | propan-2-yl N-(3-chlorophenyl)carbamate |
| InChI Key | CWJSHJJYOPWUGX-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H12ClNO2/c1-7(2)14-10(13)12-9-5-3-4-8(11)6-9/h3-7H,1-2H3,(H,12,13) |
| Canonical SMILES | CC(C)OC(=O)NC1=CC(=CC=C1)Cl |
| Isomeric SMILES | CC(C)OC(=O)NC1=CC(=CC=C1)Cl |
| Wikipedia | Chlorpropham |
| Synonyms |
Isopropyl m-chlorocarbanilate
chlorpropham
101-21-3
CHLOROPROPHAM
Chloro-IPC
CIPC
Chlorprophame
Elbanil
Isopropyl N-(3-chlorophenyl)carbamate
Metoxon
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenylcarbamic acid esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylcarbamic acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylcarbamic acid ester - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 213.661 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 197 |
| Monoisotopic Mass | 213.056 |
| Exact Mass | 213.056 |
| XLogP | 3.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| 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+ | 0.9910 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7416 |
| P-glycoprotein Substrate | Non-substrate | 0.8833 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9388 |
| Non-inhibitor | 0.9230 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9288 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7524 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7886 |
| CYP450 2D6 Substrate | Non-substrate | 0.7557 |
| CYP450 3A4 Substrate | Substrate | 0.5781 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9043 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6778 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8724 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5751 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9264 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5609 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9509 |
| Non-inhibitor | 0.9354 | |
| AMES Toxicity | Non AMES toxic | 0.5993 |
| Carcinogens | Non-carcinogens | 0.5265 |
| Fish Toxicity | High FHMT | 0.9601 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9877 |
| Honey Bee Toxicity | High HBT | 0.5269 |
| Biodegradation | Not ready biodegradable | 0.9482 |
| Acute Oral Toxicity | III | 0.8273 |
| Carcinogenicity (Three-class) | Non-required | 0.6933 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.3177 | LogS |
| Caco-2 Permeability | 1.8381 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2819 | LD50, mol/kg |
| Fish Toxicity | 0.7825 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2524 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Carrot | Japan | 0.05ppm | |||
| Huckleberry | Japan | 0.05ppm | |||
| Japanese Radish,Leaves(Including Radish) | Japan | 0.05ppm | |||
| Asparagus | Japan | 0.05ppm | |||
| Lettuce(Including Cos Lettuce And Leaf Lettuce) | Japan | 0.05ppm | |||
| Citrus fruits | 0110000 | European Union | 0.01* | 19/08/2014 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 19/08/2014 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 19/08/2014 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 19/08/2014 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 19/08/2014 | |
| Others (2) | 0110990 | European Union | 0.01* | 19/08/2014 | |
| Tree nuts | 0120000 | European Union | 0.01* | 19/08/2014 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 19/08/2014 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 19/08/2014 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 19/08/2014 | |
| Chestnuts | 0120040 | European Union | 0.01* | 19/08/2014 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 19/08/2014 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 19/08/2014 | |
| Macadamias | 0120070 | European Union | 0.01* | 19/08/2014 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 19/08/2014 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of chlorpropham (CIPC) residues, in the concrete flooring of potatostores, using quantitative (HPLC UV/VIS) and qualitative (GCMS) methods. | Chemosphere | 2018 Mar | 29258008 |
| Chronic dietary exposure to pesticide residues and associated risk in the French ELFE cohort of pregnant women. | Environ Int | 2016 Jul-Aug | 27187793 |
| Application of zirconium dioxide nanoparticle sorbent for the clean-up step inpost-harvest pesticide residue analysis. | Talanta | 2015 Nov 1 | 26452791 |
| Pesticides in fresh potatoes sold in farmers' markets in Alberta, Canada. | Bull Environ Contam Toxicol | 2011 Nov | 21909624 |
| [Multiresidue method for determination of pesticide residues in processed foodsby GC/MS]. | Shokuhin Eiseigaku Zasshi | 2009 Oct | 19897945 |
| Level and fate of chlorpropham in potatoes during storage and processing. | J Environ Sci Health B | 2009 Jan | 19089708 |
| Exposure assessment of the Belgian population to pesticide residues through fruitand vegetable consumption. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2008Jul | 18569004 |
| Rapid determination of aniline metabolites of chlorpropham in potatoes bymicellar electrokinetic chromatography using negative-charged mixed micelles and laser-induced fluorescence detection. | Electrophoresis | 2005 Aug | 15995980 |
| Chlorpropham-induced splenotoxicity and its recovery in rats. | Food Chem Toxicol | 2004 Sep | 15234077 |
| Canadian Total Diet Study in 1998: pesticide levels in foods from Whitehorse,Yukon, Canada, and corresponding dietary intake estimates. | Food Addit Contam | 2004 Mar | 15195471 |
| Effects of chlorpropham (CIPC) on the hemopoietic system of rats. | Food Chem Toxicol | 2001 Mar | 11278057 |
| Residue levels of chlorpropham in individual tubers and composite samples ofpostharvest-treated potatoes. | J Agric Food Chem | 2001 Feb | 11262017 |
| Reproductive and neurobehavioural toxicity study of chlorpropham in mice. | Food Addit Contam | 1999 Apr | 10560570 |
| Cytogenetic effects on human lymphocytes of a mixture of fifteen pesticidescommonly used in Italy. | Mutat Res | 1994 Sep | 7521012 |
| Genetic toxicity of a mixture of fifteen pesticides commonly found in the Italiandiet. | Cell Biol Toxicol | 1993 Oct-Dec | 8039010 |
| Comparison of an HPTLC and an HPLC procedure for the determination ofchlorpropham, propham and thiabendazole residues in potatoes. | Food Addit Contam | 1991 Sep-Oct | 1818834 |
Targets
- 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
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- 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
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Serine-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 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:
- 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
- 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
- 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:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 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:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 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:
- 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
- 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
- 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:
- 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 ]