T3DB: Oxadiazon

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (9)XML

Targets (9)

Record Information

Version

2.0

Creation Date

2013-04-25 07:56:53 UTC

Update Date

2014-12-24 20:26:34 UTC

Accession Number

T3D3894

Identification

Common Name

Oxadiazon

Class

Small Molecule

Description

Oxadiazon 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

MOL SDF 3D-SDF PDB SMILES InChI 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 Formula

C₁₅H₁₈Cl₂N₂O₃

Average Molecular Mass

345.221 g/mol

Monoisotopic Mass

344.069 g/mol

CAS Registry Number

19666-30-9

IUPAC Name

5-tert-butyl-3-[2,4-dichloro-5-(propan-2-yloxy)phenyl]-2,3-dihydro-1,3,4-oxadiazol-2-one

Traditional Name

oxadiazon

SMILES

CC(C)OC1=C(Cl)C=C(Cl)C(=C1)N1N=C(OC1=O)C(C)(C)C

InChI Identifier

InChI=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 Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:81786 )
Pesticides (C18496 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0029 g/L	ALOGPS
logP	4.32	ALOGPS
logP	5.31	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.83 m³·mol⁻¹	ChemAxon
Polarizability	34.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0019000000-232036ff3928b32ef3e3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3009000000-79496729227e9bf9cbfc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9351000000-14cd8b044522fc9df95d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0439000000-03b6abd07d6a43b2f843	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-3943000000-ffcef86785373f99ec3a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-4931000000-b193b553d8b05c728a4d	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004l-8932000000-3e563d9b2d48e5e2d06f	2014-10-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)	Not Available	2014-10-20	View Spectrum

Toxicity Profile

Route of Exposure

Inhalation; 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)

Metabolism

Although, 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 Values

LD50 >5000 mg/kg (oral, rat) (2); LD50 >2000 mg/kg (dermal, rabbit) (2); LC50 >1.94 mg/L (inhalation, rat) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

This is a man-made compound that is used as an herbicide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D3894.pdf

General References

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 ]
USEPA; Reregistration Eligibility Decision (RED) Database for Oxadiazon (19666-30-9). EPA 738-R-04-003 (September 2003). [Link]

Gene Regulation

Up-Regulated Genes

Gene	Gene Symbol	Gene ID	Interaction	Chromosome	Details

Down-Regulated Genes

Not 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

Type	Value	Assay Type	Assay Source
Inhibitory	2.93 uM	Not Available	BindingDB 50359941

References

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

Type	Value	Assay Type	Assay Source
AC50	2.89 uM	ATG_PXR_TRANS	Attagene
AC50	0.55 uM	ATG_PXRE_CIS	Attagene
AC50	2.85 uM	NVS_NR_hPXR	Novascreen
AC50	4.90 uM	ATG_PXR_TRANS	Attagene
AC50	0.58 uM	ATG_PXRE_CIS	Attagene
AC50	5.49 uM	NCGC_PXR_Agonist_human	NCGC
AC50	7.50 uM	NVS_NR_hPXR	Novascreen

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	0.57 uM	CLZD_CYP3A4_24	CellzDirect
AC50	0.59 uM	CLZD_CYP3A4_48	CellzDirect
AC50	0.57 uM	CLZD_CYP3A4_24	CellzDirect
AC50	0.59 uM	CLZD_CYP3A4_48	CellzDirect

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	0.63 uM	CLZD_CYP2B6_6	CellzDirect
AC50	0.60 uM	CLZD_CYP2B6_24	CellzDirect
AC50	0.63 uM	CLZD_CYP2B6_6	CellzDirect
AC50	0.60 uM	CLZD_CYP2B6_24	CellzDirect
AC50	2.32 uM	CLZD_CYP2B6_48	CellzDirect

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_SM3C_MCP1_up	BioSeek

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	3.13 uM	CLZD_CYP1A1_6	CellzDirect
AC50	10.00 uM	CLZD_CYP1A1_24	CellzDirect

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	3.69 uM	ATG_RARa_TRANS	Attagene
AC50	3.50 uM	ATG_RARa_TRANS	Attagene

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	4.54 uM	NVS_ADME_hCYP1A2	Novascreen
AC50	5.98 uM	CLZD_CYP1A2_24	CellzDirect
AC50	9.80 uM	NVS_ADME_hCYP1A2	Novascreen

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 ]

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

Type	Value	Assay Type	Assay Source
AC50	4.91 uM	CLZD_SULT2A1_48	CellzDirect

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 ]

Oxadiazon (T3D3894)

Structure for T3D3894: Oxadiazon

Targets

Binding/Activity Constants

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