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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:40:28 UTC

Update Date

2021-09-26 23:09:39 UTC

HMDB ID

HMDB0255108

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Demethoxylinuron

Description

diuron-desmethyl, also known as monomethyldiuron, 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. diuron-desmethyl is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). N-demethoxylinuron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Demethoxylinuron 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

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Monomethyldiuron	ChEBI
N-Methyl-n'-(3',4'-dichlorophenyl)-urea	ChEBI

Chemical Formula

C₈H₈Cl₂N₂O

Average Molecular Weight

219.07

Monoisotopic Molecular Weight

218.0013683

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H8Cl2N2O/c1-11-8(13)12-5-2-3-6(9)7(10)4-5/h2-4H,1H3,(H2,11,12,13)

InChI Key

IDQHRQQSSQDLTR-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
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

ureas (CHEBI:83466 )
dichlorobenzene (CHEBI:83466 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

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	2.93	ALOGPS
logP	2.31	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	54.1 m³·mol⁻¹	ChemAxon
Polarizability	20.47 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]+	143.574	30932474
DeepCCS	[M-H]-	140.274	30932474
DeepCCS	[M-2H]-	177.398	30932474
DeepCCS	[M+Na]+	152.936	30932474
AllCCS	[M+H]+	144.5	32859911
AllCCS	[M+H-H2O]+	140.8	32859911
AllCCS	[M+NH4]+	148.0	32859911
AllCCS	[M+Na]+	149.0	32859911
AllCCS	[M-H]-	139.7	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Demethoxylinuron	CNC(=O)NC1=CC=C(Cl)C(Cl)=C1	3181.3	Standard polar	33892256
N-Demethoxylinuron	CNC(=O)NC1=CC=C(Cl)C(Cl)=C1	1877.2	Standard non polar	33892256
N-Demethoxylinuron	CNC(=O)NC1=CC=C(Cl)C(Cl)=C1	2161.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Demethoxylinuron,1TMS,isomer #1	CN(C(=O)NC1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	2010.0	Semi standard non polar	33892256
N-Demethoxylinuron,1TMS,isomer #1	CN(C(=O)NC1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	1915.0	Standard non polar	33892256
N-Demethoxylinuron,1TMS,isomer #1	CN(C(=O)NC1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	2621.9	Standard polar	33892256
N-Demethoxylinuron,1TMS,isomer #2	CNC(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	1848.8	Semi standard non polar	33892256
N-Demethoxylinuron,1TMS,isomer #2	CNC(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	1844.3	Standard non polar	33892256
N-Demethoxylinuron,1TMS,isomer #2	CNC(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C	2376.1	Standard polar	33892256
N-Demethoxylinuron,2TMS,isomer #1	CN(C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C)[Si](C)(C)C	1912.2	Semi standard non polar	33892256
N-Demethoxylinuron,2TMS,isomer #1	CN(C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C)[Si](C)(C)C	2025.5	Standard non polar	33892256
N-Demethoxylinuron,2TMS,isomer #1	CN(C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C)[Si](C)(C)C	2098.4	Standard polar	33892256
N-Demethoxylinuron,1TBDMS,isomer #1	CN(C(=O)NC1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2211.6	Semi standard non polar	33892256
N-Demethoxylinuron,1TBDMS,isomer #1	CN(C(=O)NC1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2114.2	Standard non polar	33892256
N-Demethoxylinuron,1TBDMS,isomer #1	CN(C(=O)NC1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2635.1	Standard polar	33892256
N-Demethoxylinuron,1TBDMS,isomer #2	CNC(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2073.1	Semi standard non polar	33892256
N-Demethoxylinuron,1TBDMS,isomer #2	CNC(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2079.2	Standard non polar	33892256
N-Demethoxylinuron,1TBDMS,isomer #2	CNC(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C	2451.0	Standard polar	33892256
N-Demethoxylinuron,2TBDMS,isomer #1	CN(C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2372.7	Semi standard non polar	33892256
N-Demethoxylinuron,2TBDMS,isomer #1	CN(C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2435.0	Standard non polar	33892256
N-Demethoxylinuron,2TBDMS,isomer #1	CN(C(=O)N(C1=CC=C(Cl)C(Cl)=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2331.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethoxylinuron GC-MS (Non-derivatized) - 70eV, Positive	splash10-08gr-7910000000-477df2e6a926ef85fbe2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethoxylinuron GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 75V, Negative-QTOF	splash10-0a4i-0900000000-016a4aa7130e10c9bdca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 60V, Negative-QTOF	splash10-0a4i-0900000000-6b7247c0fb4bfdf72a88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 35V, Negative-QTOF	splash10-0a4i-0900000000-0cbddca59f8178930c60	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 30V, Negative-QTOF	splash10-0a4i-0900000000-73de6d2f7d963b0ca144	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 45V, Negative-QTOF	splash10-0a4i-0900000000-971a821357be947bbd4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 15V, Negative-QTOF	splash10-0a4i-0920000000-4dc888567be2d9abff04	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 55V, Negative-QTOF	splash10-0a4i-0900000000-1e1a66cc3faa0105ec7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 90V, Negative-QTOF	splash10-0a4i-0900000000-75a22f3df4b9e8ee12d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 30V, Negative-QTOF	splash10-0a4i-0900000000-1e639479cead7db2dc69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 45V, Positive-QTOF	splash10-03di-0900000000-f659ba4347818118ed35	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 30V, Positive-QTOF	splash10-02t9-0790000000-5b165025e05f5bd5cde1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 30V, Positive-QTOF	splash10-004i-0900000000-9b76589ebddebd98341b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 75V, Positive-QTOF	splash10-004i-0900000000-88105668d2c34b513edc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 10V, Negative-QTOF	splash10-0a4i-0900000000-b9bb7b5e8e916d49e2cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 40V, Negative-QTOF	splash10-0a4i-0900000000-47b4a45e6d9773d8b507	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 50V, Positive-QTOF	splash10-004i-0900000000-1e21af2c388f16bc994e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 15V, Positive-QTOF	splash10-02t9-0590000000-7682402c5d0aed69bb23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 30V, Negative-QTOF	splash10-0a4i-0900000000-8b57451251ce77582bda	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethoxylinuron 30V, Negative-QTOF	splash10-0a4i-0900000000-968a7c3d3e3da78c43a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethoxylinuron 10V, Positive-QTOF	splash10-014i-1290000000-278c6ad38034d14783b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethoxylinuron 20V, Positive-QTOF	splash10-03di-5930000000-1e4a72cd86df1ae6b08a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethoxylinuron 40V, Positive-QTOF	splash10-03e9-3900000000-fb8e6e0104d5a7975f42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethoxylinuron 10V, Negative-QTOF	splash10-066r-2790000000-a5070a0fb6f1b9898dfb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethoxylinuron 20V, Negative-QTOF	splash10-0a4r-1910000000-200c0186399516390c27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethoxylinuron 40V, Negative-QTOF	splash10-0a4i-2900000000-4690ffda4ccaff7aceb2	2016-08-03	Wishart Lab	View Spectrum

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19113

PDB ID

Not Available

ChEBI ID

83466

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 N-Demethoxylinuron (HMDB0255108)

MOL for HMDB0255108 (N-Demethoxylinuron)

3D MOL for HMDB0255108 (N-Demethoxylinuron)

3D SDF for HMDB0255108 (N-Demethoxylinuron)

3D-SDF for HMDB0255108 (N-Demethoxylinuron)

PDB for HMDB0255108 (N-Demethoxylinuron)

3D PDB for HMDB0255108 (N-Demethoxylinuron)

SMILES for HMDB0255108 (N-Demethoxylinuron)

INCHI for HMDB0255108 (N-Demethoxylinuron)

Structure for HMDB0255108 (N-Demethoxylinuron)

3D Structure for HMDB0255108 (N-Demethoxylinuron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra