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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:15:25 UTC

Update Date

2021-09-26 23:07:53 UTC

HMDB ID

HMDB0254109

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Linuron

Description

Linuron, also known as afalon, 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. It is known to inhibit photosynthesis (photosystem II). Linuron is a weak competitive inhibitor of androgen receptor binding and it inhibits androgen-induced gene expression in vitro. Linuron is an extremely weak basic (essentially neutral) compound (based on its pKa). Linuron is a potentially toxic compound. Linuron affects the male reproductive system of the offspring after maternal exposure during mid and late pregnancy. Linuron is an herbicide for the pre- and post-emergence control of annual grass and broad-leaved weeds using selective and systemic action with contact and residual action. This may partially contribute to the malformations of androgen-dependent tissues in male rats. This compound has been identified in human blood as reported by (PMID: 31557052 ). Linuron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Linuron is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

 
  Mrv0541 09271209192D          
 
 15 15  0  0  0  0            999 V2000
   14.8308   -9.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8308  -10.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5475  -10.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2601  -10.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2601   -9.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5475   -9.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9700   -9.1552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6830   -9.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3961   -9.1511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1050   -9.5573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6789  -10.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3919   -8.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1177  -10.8011    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5809  -11.6302    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8181   -9.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  7  8  1  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  2  0  0  0  0
  9 10  1  0  0  0  0
  4  5  1  0  0  0  0
  8 11  2  0  0  0  0
  5  6  2  0  0  0  0
  9 12  1  0  0  0  0
  6  1  1  0  0  0  0
  2 13  1  0  0  0  0
  3 14  1  0  0  0  0
  5  7  1  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254109

> <DATABASE_NAME>
hmdb

> <SMILES>
CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)

> <INCHI_KEY>
XKJMBINCVNINCA-UHFFFAOYSA-N

> <FORMULA>
C9H10Cl2N2O2

> <MOLECULAR_WEIGHT>
249.094

> <EXACT_MASS>
248.011932988

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.25931897872309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3,4-dichlorophenyl)-3-methoxy-3-methylurea

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.6839550633333333

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.938887825222496

> <JCHEM_PKA_STRONGEST_BASIC>
-4.680110919015409

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
60.3509

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linuron

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-12         0                                  
HETATM    1  C   UNK     0      27.684 -17.856   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.684 -19.396   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.022 -20.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.352 -19.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.352 -17.856   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.022 -17.090   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      31.677 -17.090   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      33.008 -17.848   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      34.339 -17.082   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      35.663 -17.840   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      33.001 -19.388   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      34.332 -15.542   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      26.353 -20.162   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0      29.084 -21.710   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      36.994 -17.067   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    8    5                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   15                                                       
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    2                                                            
CONECT   14    3                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methoxy-1-methyl-3-(3,4-dichlorophenyl)urea	ChEBI
3-(3,4-Dichlorophenyl)-1-methoxy-1-methylurea	ChEBI
N'-(3,4-dichlorophenyl)-N-methoxy-N-methyl urea	ChEBI
Afalon	MeSH

Chemical Formula

C₉H₁₀Cl₂N₂O₂

Average Molecular Weight

249.094

Monoisotopic Molecular Weight

248.011932988

IUPAC Name

1-(3,4-dichlorophenyl)-3-methoxy-3-methylurea

Traditional Name

linuron

CAS Registry Number

Not Available

SMILES

CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1

InChI Identifier

InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)

InChI Key

XKJMBINCVNINCA-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

N-phenylureas

Direct Parent

N-phenylureas

Alternative Parents

Substituents

N-phenylurea
1,2-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Carbonic acid derivative
Organic nitrogen compound
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ureas (CHEBI:6482 )
dichlorobenzene (CHEBI:6482 )
Phenylurea herbicides (C11007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0254109)
Membrane (HMDB: HMDB0254109)

Organelle

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Metabolic Pathways (HMDB: HMDB0254109)
Aflatoxin Biosynthesis (HMDB: HMDB0254109)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.82	ALOGPS
logP	2.68	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.35 m³·mol⁻¹	ChemAxon
Polarizability	23.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	149.183	30932474
DeepCCS	[M-H]-	146.825	30932474
DeepCCS	[M-2H]-	180.897	30932474
DeepCCS	[M+Na]+	155.622	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	146.8	32859911
AllCCS	[M+NH4]+	153.9	32859911
AllCCS	[M+Na]+	154.8	32859911
AllCCS	[M-H]-	149.6	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	151.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linuron	CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1	2956.9	Standard polar	33892256
Linuron	CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1	1896.5	Standard non polar	33892256
Linuron	CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1	1983.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linuron,1TMS,isomer #1	CON(C)C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	1882.7	Semi standard non polar	33892256
Linuron,1TMS,isomer #1	CON(C)C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	1977.6	Standard non polar	33892256
Linuron,1TMS,isomer #1	CON(C)C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	2304.7	Standard polar	33892256
Linuron,1TBDMS,isomer #1	CON(C)C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2118.7	Semi standard non polar	33892256
Linuron,1TBDMS,isomer #1	CON(C)C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2198.8	Standard non polar	33892256
Linuron,1TBDMS,isomer #1	CON(C)C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2415.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Linuron GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-3910000000-06403414f74cd43e045e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linuron GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9200000000-02a9a624235ddb48448d	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 55V, Positive-QTOF	splash10-053r-0900000000-58defb2ae9c51a83691e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 45V, Positive-QTOF	splash10-0a59-0900000000-fc28f465e47143fb5927	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 60V, Positive-QTOF	splash10-0a59-0900000000-63e2a0b93419ffc4eafb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 35V, Positive-QTOF	splash10-0bu1-1930000000-ab84eba117f7c5ab98ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 40V, Negative-QTOF	splash10-0f6t-0890000000-f1b31df027603c7cd878	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 30V, Positive-QTOF	splash10-0a5a-0940000000-4c2350ca6138da576cdf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 55V, Positive-QTOF	splash10-0a59-0900000000-248384e486fe00066678	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 75V, Positive-QTOF	splash10-06si-0900000000-7190cc3af8bf9fde6ef9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 15V, Positive-QTOF	splash10-0002-0190000000-43475d3d09de3d66940a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 15V, Negative-QTOF	splash10-0a4i-0910000000-f709c06637f21ffef280	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 80V, Positive-QTOF	splash10-01q9-0900000000-c2ba2c42df804483c4bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 35V, Positive-QTOF	splash10-053r-0900000000-5f48adbb98c12803d608	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 30V, Negative-QTOF	splash10-0a4i-0910000000-59ba8adaef398a8bd29a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 45V, Negative-QTOF	splash10-0a4i-0920000000-4e379a2e3c68a80a9f39	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 75V, Negative-QTOF	splash10-03dj-0970000000-7fc321d13458dd5f03f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 60V, Negative-QTOF	splash10-0bt9-0950000000-3807c2876fc72308cc65	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 50V, Positive-QTOF	splash10-001i-0900000000-d7ad86577f8019000d68	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 90V, Negative-QTOF	splash10-0002-0910000000-5f4398f81ba0940aa138	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linuron 30V, Positive-QTOF	splash10-08gi-0900000000-844c0e7b8f1bae30354d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linuron 10V, Positive-QTOF	splash10-0002-2390000000-69016a05781705508d3e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linuron 20V, Positive-QTOF	splash10-03di-9340000000-21d61a1ea4afdade4fdf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linuron 40V, Positive-QTOF	splash10-000i-8900000000-3ceff76441f309a84632	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linuron 10V, Negative-QTOF	splash10-0002-1090000000-09719403e6831b7d7ae5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linuron 20V, Negative-QTOF	splash10-02tj-1490000000-00d02fd3109d9782a7cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linuron 40V, Negative-QTOF	splash10-0550-9700000000-8e7c824eb58d822210ad	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11007

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Linuron

METLIN ID

Not Available

PubChem Compound

9502

PDB ID

Not Available

ChEBI ID

6482

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Linuron (HMDB0254109)

MOL for HMDB0254109 (Linuron)

3D MOL for HMDB0254109 (Linuron)

3D SDF for HMDB0254109 (Linuron)

3D-SDF for HMDB0254109 (Linuron)

PDB for HMDB0254109 (Linuron)

3D PDB for HMDB0254109 (Linuron)

SMILES for HMDB0254109 (Linuron)

INCHI for HMDB0254109 (Linuron)

Structure for HMDB0254109 (Linuron)

3D Structure for HMDB0254109 (Linuron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra