Diphenylamine
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Basic Info
| Common Name | Diphenylamine(F05408) |
| 2D Structure | |
| Description | Diphenylamine is found in coriander. Diphenylamine is used for control of superficial scald in stored apples Diphenylamine is the organic compound with the formula (C6H5)2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities. It is a weak base, with a KB of 10 14. With strong acids, it forms the water soluble salt. Diphenylamine belongs to the family of Aromatic Homomonocyclic Compounds. These are aromatic compounds containig only one ring, which is homocyclic. |
| FRCD ID | F05408 |
| CAS Number | 122-39-4 |
| PubChem CID | 11487 |
| Formula | C12H11N |
| IUPAC Name | N-phenylaniline |
| InChI Key | DMBHHRLKUKUOEG-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H |
| Canonical SMILES | C1=CC=C(C=C1)NC2=CC=CC=C2 |
| Isomeric SMILES | C1=CC=C(C=C1)NC2=CC=CC=C2 |
| Wikipedia | Diphenylamine |
| Synonyms |
Diphenylamine
N-Phenylaniline
122-39-4
N-Phenylbenzenamine
Anilinobenzene
Benzenamine, N-phenyl-
N,N-DIPHENYLAMINE
Phenylaniline
Scaldip
N-Phenylbenzeneamine
|
| Classifies |
Pollutant
Pesticide
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Aniline and substituted anilines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aniline and substituted anilines |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Aniline or substituted anilines - Secondary amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 169.227 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Complexity | 116 |
| Monoisotopic Mass | 169.089 |
| Exact Mass | 169.089 |
| XLogP | 3.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.9730 |
| Human Intestinal Absorption | HIA+ | 0.9849 |
| Caco-2 Permeability | Caco2+ | 0.9022 |
| P-glycoprotein Substrate | Non-substrate | 0.8597 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9265 |
| Non-inhibitor | 0.9428 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8064 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5991 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7817 |
| CYP450 2D6 Substrate | Non-substrate | 0.8893 |
| CYP450 3A4 Substrate | Non-substrate | 0.7542 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8167 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5217 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.6147 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.9259 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9376 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7860 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9333 |
| Non-inhibitor | 0.8909 | |
| AMES Toxicity | Non AMES toxic | 0.7618 |
| Carcinogens | Non-carcinogens | 0.5209 |
| Fish Toxicity | High FHMT | 0.9050 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9946 |
| Honey Bee Toxicity | Low HBT | 0.6287 |
| Biodegradation | Not ready biodegradable | 0.8121 |
| Acute Oral Toxicity | III | 0.9158 |
| Carcinogenicity (Three-class) | Non-required | 0.6625 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4474 | LogS |
| Caco-2 Permeability | 1.9858 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1474 | LD50, mol/kg |
| Fish Toxicity | 0.7035 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0925 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Kidney | 1017040 | European Union | 0.05* | 11/02/2016 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 11/02/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 11/02/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 11/02/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 11/02/2016 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 11/02/2016 | |
| Others (2) | 0110990 | European Union | 0.05* | 11/02/2016 | |
| Tree nuts | 0120000 | European Union | 0.05* | 11/02/2016 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 11/02/2016 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 11/02/2016 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 11/02/2016 | |
| Chestnuts | 0120040 | European Union | 0.05* | 11/02/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 11/02/2016 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 11/02/2016 | |
| Macadamias | 0120070 | European Union | 0.05* | 11/02/2016 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 11/02/2016 | |
| Pistachios | 0120100 | European Union | 0.05* | 11/02/2016 | |
| Walnuts | 0120110 | European Union | 0.05* | 11/02/2016 | |
| Others (2) | 0120990 | European Union | 0.05* | 11/02/2016 | |
| Apples (Crab apples/wild apples, Tejocotes,) | 0130010 | European Union | 0.1 | 11/02/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Substituted Diphenylamine Antioxidants and Benzotriazole UV Stabilizers inAquatic Organisms in the Great Lakes of North America: Terrestrial Exposure andBiodilution. | Environ Sci Technol | 2018 Feb 6 | 29286648 |
| Menaquinone-7 production from maize meal hydrolysate by Bacillus isolates withdiphenylamine and analogue resistance. | J Zhejiang Univ Sci B | 2017 Jun | 28585422 |
| Residues of plant protection products in grey partridge eggs in French cerealecosystems. | Environ Sci Pollut Res Int | 2016 May | 26841780 |
| Land Spreading of Wastewaters from the Fruit-Packaging Industry and Potential Effects on Soil Microbes: Effects of the Antioxidant Ethoxyquin and Its Metabolites on Ammonia Oxidizers. | Appl Environ Microbiol | 2016 Jan 15 | 26590271 |
| Determination of Diphenylamine in Agricultural Products by HPLC-FL. | Shokuhin Eiseigaku Zasshi | 2016 | 28025454 |
| A method to detect diphenylamine contamination of apple fruit and storages using headspace solid phase micro-extraction and gas chromatography/mass spectroscopy. | Food Chem | 2014 Oct 1 | 24799236 |
| A novel dsDNA/polydiphenylamine-4-sulfonic acid electrochemical biosensor for selective detection of the toxic catechol and related DNA damage. | Analyst | 2013 Feb 21 | 23259155 |
| New spectrophotometric methods for the determinations of hydrogen sulfide presentin the samples of lake water, industrial effluents, tender coconut, sugarcanejuice and egg. | Spectrochim Acta A Mol Biomol Spectrosc | 2012 Oct | 22889607 |
| In situ analysis of agrochemical residues on fruit using ambient ionization on a handheld mass spectrometer. | Analyst | 2011 Nov 7 | 21892448 |
| Rapid determination of diphenylamine residues in apples and pears with a singlemulticommuted fluorometric optosensor. | J Agric Food Chem | 2005 Dec 28 | 16366668 |
| Carbendazim and metalaxyl residues in post-harvest treated apples. | Food Addit Contam | 2003 Aug | 13129789 |
| Analysis of pesticide residues in mixed fruit and vegetable extracts by directsample introduction/gas chromatography/tandem mass spectrometry. | J AOAC Int | 2000 May-Jun | 10868593 |
| UVA-induced oxidative damage to rat liver nuclei: reduction of iron ions and the relationship between lipid peroxidation and DNA damage. | Mutat Res | 1999 Jan 13 | 10036333 |
| Multivariate analysis of superficial scald susceptibility on Granny Smith apples dipped with different postharvest treatments. | J Agric Food Chem | 1999 Dec | 10606542 |
| Determination of o-phenylphenol, diphenylamine, and propargite pesticide residuesin selected fruits and vegetables by gas chromatography/mass spectrometry. | J AOAC Int | 1997 May-Jun | 9170661 |
| Ascorbic acid inhibits lipid peroxidation but enhances DNA damage in rat livernuclei incubated with iron ions. | Free Radic Res | 1997 Jun | 9212351 |
| Monitoring of domestic and imported apples and rice by the U.S. Food and DrugAdministration pesticide program. | J AOAC Int | 1997 Jul-Aug | 9241850 |
| Oxidative liver DNA damage in rats treated with pesticide mixtures. | Toxicology | 1997 Feb 14 | 9020199 |
| Investigation of regional glutathione levels in a model of chemically-induced renal papillary necrosis. | Food Chem Toxicol | 1996 May | 8655099 |
| Cytogenetic effects on human lymphocytes of a mixture of fifteen pesticidescommonly used in Italy. | Mutat Res | 1994 Sep | 7521012 |
Targets
- General Function:
- Hydroxymethylglutaryl-coa synthase activity
- Specific Function:
- This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
- Gene Name:
- HMGCS2
- Uniprot ID:
- P54868
- Molecular Weight:
- 56634.915 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:
- 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
- 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:
- 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:
- 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:
- 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:
- 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
- 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 ]