You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.

Oxadiazon (T3D3894)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (9)XML
Targets (9)
Record Information
Version2.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2014-12-24 20:26:34 UTC
Accession NumberT3D3894
Identification
Common NameOxadiazon
ClassSmall Molecule
DescriptionOxadiazon is used as pre-emergence and post-emergence herbicide. It is mainly used for cotton, rice, soybean and sunflower and acts by inhibiting protoporphyrinogen oxidase (PPO).
Compound Type
  • Ether
  • Herbicide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
2-tert-Butyl-4-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolin-5-one
2-tert-Butyl-4-(2,4-dichloro-5-isopropoxyphenyl)-5-oxo-1,3,4-oxadiazoline
2-tert-Butyl-4-(2,4-dichloro-5-isopropoxyphenyl)-D2-1,3,4-oxadiazolin-5-one
2-tert-Butyl-4-(2,4-dichloro-5-isopropyloxyphenyl)-1,3,4-oxadiazolin-5-one
3-(2,4-Dichloro-5-(1-methylethoxy)phenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one
3-(2,4-Dichloro-5-isopropoxyphenyl)-5-(2-methyl-2-propanyl)-1,3,4-oxadiazol-2(3H)-one
5-tert-Butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazol-2(3H)-one
5-tert-Butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolin-2-one
5-tert-butyl-3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-1,3,4-oxadiazol-2(3H)-one
Oxadiazone
Oxydiazon
Ronstan
Chemical FormulaC15H18Cl2N2O3
Average Molecular Mass345.221 g/mol
Monoisotopic Mass344.069 g/mol
CAS Registry Number19666-30-9
IUPAC Name5-tert-butyl-3-[2,4-dichloro-5-(propan-2-yloxy)phenyl]-2,3-dihydro-1,3,4-oxadiazol-2-one
Traditional Nameoxadiazon
SMILESCC(C)OC1=C(Cl)C=C(Cl)C(=C1)N1N=C(OC1=O)C(C)(C)C
InChI IdentifierInChI=1S/C15H18Cl2N2O3/c1-8(2)21-12-7-11(9(16)6-10(12)17)19-14(20)22-13(18-19)15(3,4)5/h6-8H,1-5H3
InChI KeyInChIKey=CHNUNORXWHYHNE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • Phenoxy compound
  • 1,3-dichlorobenzene
  • Phenol ether
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • 1,3,4-oxadiazole
  • Azole
  • Oxadiazole
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP4.32ALOGPS
logP5.31ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area51.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.83 m³·mol⁻¹ChemAxon
Polarizability34.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0019000000-232036ff3928b32ef3e32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3009000000-79496729227e9bf9cbfc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9351000000-14cd8b044522fc9df95d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0439000000-03b6abd07d6a43b2f8432016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-3943000000-ffcef86785373f99ec3a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-4931000000-b193b553d8b05c728a4d2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-8932000000-3e563d9b2d48e5e2d06f2014-10-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-10-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Not Available2014-10-20View Spectrum
Toxicity Profile
Route of ExposureInhalation; dermal. (2)
Mechanism of Toxicity'Oxadiazon is a member of the oxadiazole class of herbicides. While current data are limited, EPA has evidence that compounds within a class may share a common mechanism of toxicity. At this time, the Agency does not have sufficient data concerning common mechanism issues to determine whether or not oxadiazon shares a common mechanism of toxicity with other substances, including other oxadiazoles or other probable human carcinogens.' (2)
MetabolismAlthough, examples of all oxadiazole isomers are known, only the biotransformation pathways of compounds containing 1,2,4-oxdiazole rings have been reported so far. (1)
Toxicity ValuesLD50 >5000 mg/kg (oral, rat) (2); LD50 >2000 mg/kg (dermal, rabbit) (2); LC50 >1.94 mg/L (inhalation, rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesThis is a man-made compound that is used as an herbicide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID29732
ChEMBL IDCHEMBL1080648
ChemSpider ID27628
KEGG IDC18496
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3894.pdf
General References
  1. Dalvie DK, Kalgutkar AS, Khojasteh-Bakht SC, Obach RS, O'Donnell JP: Biotransformation reactions of five-membered aromatic heterocyclic rings. Chem Res Toxicol. 2002 Mar;15(3):269-99. [11896674 ]
  2. USEPA; Reregistration Eligibility Decision (RED) Database for Oxadiazon (19666-30-9). EPA 738-R-04-003 (September 2003). [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

Target Details
1. Protoporphyrinogen oxidase
General Function:
Oxygen-dependent protoporphyrinogen oxidase activity
Specific Function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
Gene Name:
PPOX
Uniprot ID:
P50336
Molecular Weight:
50764.8 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory2.93 uMNot AvailableBindingDB 50359941
References
  1. Zuo Y, Yang SG, Jiang LL, Hao GF, Wang ZF, Wu QY, Xi Z, Yang GF: Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors. Bioorg Med Chem. 2012 Jan 1;20(1):296-304. doi: 10.1016/j.bmc.2011.10.079. Epub 2011 Nov 10. [22130420 ]
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.89 uMATG_PXR_TRANSAttagene
AC500.55 uMATG_PXRE_CISAttagene
AC502.85 uMNVS_NR_hPXRNovascreen
AC504.90 uMATG_PXR_TRANSAttagene
AC500.58 uMATG_PXRE_CISAttagene
AC505.49 uMNCGC_PXR_Agonist_humanNCGC
AC507.50 uMNVS_NR_hPXRNovascreen
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
3. 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
AC500.57 uMCLZD_CYP3A4_24CellzDirect
AC500.59 uMCLZD_CYP3A4_48CellzDirect
AC500.57 uMCLZD_CYP3A4_24CellzDirect
AC500.59 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
4. 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
AC500.63 uMCLZD_CYP2B6_6CellzDirect
AC500.60 uMCLZD_CYP2B6_24CellzDirect
AC500.63 uMCLZD_CYP2B6_6CellzDirect
AC500.60 uMCLZD_CYP2B6_24CellzDirect
AC502.32 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
5. C-C motif chemokine 2
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
CCL2
Uniprot ID:
P13500
Molecular Weight:
11024.87 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.48 uMBSK_SM3C_MCP1_upBioSeek
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 1A1
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.13 uMCLZD_CYP1A1_6CellzDirect
AC5010.00 uMCLZD_CYP1A1_24CellzDirect
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. Retinoic acid receptor alpha
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
Gene Name:
RARA
Uniprot ID:
P10276
Molecular Weight:
50770.805 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.69 uMATG_RARa_TRANSAttagene
AC503.50 uMATG_RARa_TRANSAttagene
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. 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
AC504.54 uMNVS_ADME_hCYP1A2Novascreen
AC505.98 uMCLZD_CYP1A2_24CellzDirect
AC509.80 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
9. 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
AC504.91 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 ]