Diuron (T3D4500)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (8)XML
Targets (8)
Record Information
Version2.0
Creation Date2014-08-29 06:51:42 UTC
Update Date2014-12-24 20:26:51 UTC
Accession NumberT3D4500
Identification
Common NameDiuron
ClassSmall Molecule
DescriptionDiuron, also known as DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea), is an herbicide in the urea chemical family that inhibits photosynthesis. It was introduced by Bayer in 1954 under the trade name of Diuron. DCMU is a very specific and sensitive inhibitor of photosynthesis, the process by which plants use light, water, and carbon di-oxide from the atmosphere to form plant sugars and cellulose. Diuron blocks electron transport at a critical point in this process. It blocks the plastoquinone binding site of photosystem II, disallowing the electron flow from where it is generated, in photosystem II, to plastoquinone. This interrupts the photosynthetic electron transport chain in photosynthesis and thus reduces the ability of the plant to turn light energy into chemical energy (ATP and reductant potential).
Compound Type
  • Amine
  • Herbicide
  • Household Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,1-Dimethyl-3-(3,4-dichlorophenyl)urea, 1-(3,4-Dichlorophenyl)-3,3-dimethylurea
1-(3,4-Dichlorophenyl)-3,3-dimethyluree
3-(3,4-Dichlor-phenyl)-1,1-dimethyl-harnstoff
3-(3,4-Dichloro-phenyl)-1,1-dimethyl-urea
3-(3,4-Dichlorophenyl)-1,1-dimethylurea
DCMU
DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea)
N'-(3,4-dichlorophenyl)-N,N-dimethylurea
N,N,-Dimethyl-n'-(3,4-dichlorophenyl)urea
N-(3,4-Dichlorophenyl)-n',n'-dimethylurea
Chemical FormulaC9H10Cl2N2O
Average Molecular Mass233.095 g/mol
Monoisotopic Mass232.017 g/mol
CAS Registry Number330-54-1
IUPAC Name1-(3,4-dichlorophenyl)-3,3-dimethylurea
Traditional Namedynex
SMILESCN(C)C(O)=NC1=CC(Cl)=C(Cl)C=C1
InChI IdentifierInChI=1S/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
InChI KeyInChIKey=XMTQQYYKAHVGBJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassN-phenylureas
Direct ParentN-phenylureas
Alternative Parents
Substituents
  • N-phenylurea
  • 1,2-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Urea
  • Carbonic acid derivative
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Cytoskeleton
  • Endoplasmic reticulum
  • Extracellular
  • Lysosome
  • Membrane
  • Microsome
  • Microtubule
  • Mitochondrion
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Oxidative phosphorylationNot Availablemap00190
Circadian rhythmNot Availablemap04710
Atrazine DegradationNot AvailableNot Available
Cell cycleNot Availablemap04110
Metabolic PathwaysNot AvailableNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.92ALOGPS
logP2.53ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity59 m³·mol⁻¹ChemAxon
Polarizability22.52 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2020-08-04View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-001i-0090000000-b0bd25ab923ef26df58b2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-0019-0960000000-425969fab7d1de410afa2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-000j-0900000000-9d6d97dd4fe843fdd0522020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-0002-0900000000-d6689f92e144831e9d7a2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 16V, negativesplash10-000i-0900000000-e77c44a0fe464fe4b61d2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 6V, negativesplash10-001i-0090000000-e881c96fe6f6bb880e312020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, negativesplash10-001i-0190000000-76ea8ede6c766fe0da4a2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 20V, negativesplash10-0019-0960000000-bb49ac188469caa12e4a2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 27V, negativesplash10-000i-0910000000-09aee4408526f79b5be22020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 34V, negativesplash10-000b-0900000000-6a4ba91cc6a63e2a39ba2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 41V, negativesplash10-0002-0900000000-879e75c29f5ac165c0182020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 25V, negativesplash10-001i-0090000000-1b4c60c64a5cefa3fa6c2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 37V, negativesplash10-001j-0590000000-fa091daa831961138a002020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 16V, negativesplash10-000i-0900000000-48cded5750b2ac5125052020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 16V, negativesplash10-001i-0590000000-509427d3b080764e28812020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , negativesplash10-001r-0890000000-ac3ea5258715ba65f84a2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 26V, negativesplash10-000i-0920000000-8f3bb4e7a3d23f7d24872020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-000i-0900000000-c319262d88d0bdc2c84e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-000b-0900000000-27449134e23ed27e054d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0590000000-509427d3b080764e28812021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Negativesplash10-000i-0900000000-e75dc87d27f87333f8402021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0002-0900000000-b9e90b15f1af12882c542021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-001i-0090000000-74483962da2bb7e0637d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-48cded5750b2ac5125052021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 80V, Negativesplash10-001j-0590000000-fa091daa831961138a002021-09-20View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00e9-9220000000-867bc41c9b68124d9eff2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityDiuron has been reported to bind to androgen receptors. This suggests that diuron may block the receptors and result in the toxicity on the reproductive system.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsDiuron has reproductive, teratogenic effects and organ toxicity to mammals. Diuron induces urinary bladder cancer, mammary gland carcinoma and hepatocellular adenomas in mice, kidney toumors and testicular interstitial cell adenomas in rats. High level diuron exposure can cause central nervous system depression. Chronic exposure can affect bone marrow, spleen in rats. Anemia, increase mortality, growth retardation are also seen.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID3120
ChEMBL IDCHEMBL278489
ChemSpider ID3008
KEGG IDC18428
UniProt IDNot Available
OMIM ID
ChEBI IDCHEBI:116509
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4500.pdf
General References
  1. EPA [Link]
  2. EVIDENCE ON THE DEVELOPMENTAL AND REPRODUCTIVE TOXICITY OF Diuron. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Aryl hydrocarbon receptor
General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
References
  1. Noguerol TN, Boronat S, Casado M, Raldua D, Barcelo D, Pina B: Evaluating the interactions of vertebrate receptors with persistent pollutants and antifouling pesticides using recombinant yeast assays. Anal Bioanal Chem. 2006 Jul;385(6):1012-9. Epub 2006 May 17. [16705413 ]
Target Details
2. Nuclear receptor subfamily 1 group I member 2
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
  1. Kojima H, Sata F, Takeuchi S, Sueyoshi T, Nagai T: Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87. doi: 10.1016/j.tox.2010.11.008. Epub 2010 Nov 27. [21115097 ]
Target Details
3. Solute carrier organic anion transporter family member 1B1
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.32 uMCLZD_SLCO1B1_48CellzDirect
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 ]
Target Details
4. Cytochrome P450 1A2
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.74 uMCLZD_CYP1A2_6CellzDirect
AC500.82 uMNVS_ADME_hCYP1A2Novascreen
AC502.20 uMNVS_ADME_hCYP1A2Novascreen
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 ]
Target Details
5. UDP-glucuronosyltransferase 1-1
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.86 uMCLZD_UGT1A1_24CellzDirect
AC506.21 uMCLZD_UGT1A1_48CellzDirect
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 ]
Target Details
6. Cytochrome P450 2B6
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.63 uMCLZD_CYP2B6_6CellzDirect
AC504.98 uMCLZD_CYP2B6_24CellzDirect
AC509.19 uMCLZD_CYP2B6_48CellzDirect
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 ]
Target Details
7. Cytochrome P450 3A4
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.37 uMCLZD_CYP3A4_24CellzDirect
AC505.27 uMCLZD_CYP3A4_48CellzDirect
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 ]
Target Details
8. Bile salt sulfotransferase
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.04 uMCLZD_SULT2A1_24CellzDirect
AC505.75 uMCLZD_SULT2A1_48CellzDirect
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 ]