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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:04:19 UTC

Update Date

2021-09-26 23:08:50 UTC

HMDB ID

HMDB0254685

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metribuzin

Description

Metribuzin belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. Metribuzin is a moderately basic compound (based on its pKa). Metribuzin is a potentially toxic compound. This compound has been identified in human blood as reported by (PMID: 31557052 ). Metribuzin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metribuzin 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                                 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      30.631 -18.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.631 -19.543   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      31.975 -20.317   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      33.303 -19.543   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      33.303 -18.003   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      31.975 -17.237   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      29.298 -20.318   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0      34.636 -20.316   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      29.298 -17.236   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.299 -15.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.965 -18.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.915 -16.299   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      31.978 -21.859   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      36.001 -19.531   0.000  0.00  0.00           C+0
CONECT    1    2    9    6                                                  
CONECT    2    1    7    3                                                  
CONECT    3    2    4   13                                                  
CONECT    4    8    3    5                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    4   14                                                       
CONECT    9    1   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    3                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0254685
HETATM    1  C1  UNL     1       4.684  -0.494   0.673  1.00  0.00           C  
HETATM    2  S1  UNL     1       3.658   0.924   1.145  1.00  0.00           S  
HETATM    3  C2  UNL     1       1.927   0.551   0.840  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.157  -0.022   1.774  1.00  0.00           N  
HETATM    5  N2  UNL     1      -0.128  -0.313   1.583  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.665  -0.010   0.390  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.086  -0.295   0.083  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.107  -1.241  -1.110  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.740   1.029  -0.263  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.784  -0.988   1.220  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.098   0.580  -0.594  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.345   0.888  -1.730  1.00  0.00           O  
HETATM   13  N3  UNL     1       1.413   0.859  -0.351  1.00  0.00           N  
HETATM   14  N4  UNL     1       2.182   1.455  -1.345  1.00  0.00           N  
HETATM   15  H1  UNL     1       4.954  -1.073   1.587  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.117  -1.159  -0.002  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.591  -0.168   0.102  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.020  -1.871  -1.112  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.204  -1.901  -0.996  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.002  -0.726  -2.066  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.886   1.159  -1.344  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.113   1.891   0.083  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.678   1.095   0.326  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.436  -0.296   1.802  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.069  -1.509   1.900  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.462  -1.769   0.820  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.490   2.445  -1.192  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.457   0.957  -2.223  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5
CONECT    5    6    6
CONECT    6    7   11
CONECT    7    8    9   10
CONECT    8   18   19   20
CONECT    9   21   22   23
CONECT   10   24   25   26
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Amino-6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one	ChEBI
4-amino-6-Tert-butyl- 3-(methylthio)-S-triazin-5-(4H)-one	MeSH
Lexone	MeSH
Sencor	MeSH
Zenkor	MeSH

Chemical Formula

C₈H₁₄N₄OS

Average Molecular Weight

214.288

Monoisotopic Molecular Weight

214.08883178

IUPAC Name

4-amino-6-tert-butyl-3-(methylsulfanyl)-4,5-dihydro-1,2,4-triazin-5-one

Traditional Name

sencor

CAS Registry Number

Not Available

SMILES

CSC1=NN=C(C(=O)N1N)C(C)(C)C

InChI Identifier

InChI=1S/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3

InChI Key

FOXFZRUHNHCZPX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Aryl thioethers

Alternative Parents

Substituents

Aryl thioether
Alkylarylthioether
Triazine
1,2,4-triazine
Heteroaromatic compound
Lactam
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cyclic ketone (CHEBI:34846 )
organic sulfide (CHEBI:34846 )
1,2,4-triazines (CHEBI:34846 )
Triazine herbicides (C14332 )
Triazinone herbicides (C14332 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0254685)
Extracellular (HMDB: HMDB0254685)

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	1.54	ALOGPS
logP	1.96	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	2.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58 m³·mol⁻¹	ChemAxon
Polarizability	22.08 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]+	148.136	30932474
DeepCCS	[M-H]-	145.74	30932474
DeepCCS	[M-2H]-	179.289	30932474
DeepCCS	[M+Na]+	154.212	30932474
AllCCS	[M+H]+	144.2	32859911
AllCCS	[M+H-H2O]+	140.5	32859911
AllCCS	[M+NH4]+	147.7	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	147.8	32859911
AllCCS	[M+Na-2H]-	148.8	32859911
AllCCS	[M+HCOO]-	149.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metribuzin	CSC1=NN=C(C(=O)N1N)C(C)(C)C	2327.2	Standard polar	33892256
Metribuzin	CSC1=NN=C(C(=O)N1N)C(C)(C)C	1785.8	Standard non polar	33892256
Metribuzin	CSC1=NN=C(C(=O)N1N)C(C)(C)C	1878.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metribuzin,1TMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N[Si](C)(C)C	1889.4	Semi standard non polar	33892256
Metribuzin,1TMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N[Si](C)(C)C	1817.7	Standard non polar	33892256
Metribuzin,1TMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N[Si](C)(C)C	3056.6	Standard polar	33892256
Metribuzin,2TMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N([Si](C)(C)C)[Si](C)(C)C	1910.5	Semi standard non polar	33892256
Metribuzin,2TMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N([Si](C)(C)C)[Si](C)(C)C	1950.5	Standard non polar	33892256
Metribuzin,2TMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N([Si](C)(C)C)[Si](C)(C)C	2419.6	Standard polar	33892256
Metribuzin,1TBDMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N[Si](C)(C)C(C)(C)C	2097.9	Semi standard non polar	33892256
Metribuzin,1TBDMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N[Si](C)(C)C(C)(C)C	2036.0	Standard non polar	33892256
Metribuzin,1TBDMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N[Si](C)(C)C(C)(C)C	3055.2	Standard polar	33892256
Metribuzin,2TBDMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2275.3	Semi standard non polar	33892256
Metribuzin,2TBDMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2395.5	Standard non polar	33892256
Metribuzin,2TBDMS,isomer #1	CSC1=NN=C(C(C)(C)C)C(=O)N1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2555.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metribuzin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bta-8910000000-710f049556a8522ae817	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metribuzin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9600000000-f01ca2de50860ccf843e	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 90V, Positive-QTOF	splash10-0a4i-9000000000-c07c5cae60e1ac822ccb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 30V, Positive-QTOF	splash10-014i-0090000000-d52c6a7b999f55d0e51b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 45V, Positive-QTOF	splash10-014r-0590000000-199702458074442acb73	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 40V, Positive-QTOF	splash10-053r-0900000000-a45f75409c3af6a6054d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 75V, Positive-QTOF	splash10-0a4i-9200000000-3e63f9eec9dafaae1eeb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 75V, Positive-QTOF	splash10-0a4i-9200000000-7a6cdf083625b2ccdc22	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 60V, Positive-QTOF	splash10-053i-9500000000-9d0d20117a9fb7fae1c7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 35V, Positive-QTOF	splash10-000i-0900000000-202a3c2453ce7f8e089d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 90V, Positive-QTOF	splash10-0ac0-9300000000-bc39f73488d0647f38c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 60V, Positive-QTOF	splash10-000i-3920000000-3bfff666c7c355ce48ae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 75V, Positive-QTOF	splash10-05a9-9800000000-057a7c7692587183822a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 45V, Positive-QTOF	splash10-014r-0690000000-d3c30e5bfb074e0a0f7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 30V, Positive-QTOF	splash10-014i-0090000000-9398ba17da28f7fce470	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 35V, Positive-QTOF	splash10-014i-0290000000-e3451353e06b6560e3ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 60V, Positive-QTOF	splash10-000i-3920000000-a4f0e416c96410fa4f28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 75V, Positive-QTOF	splash10-05a9-9800000000-42e2260551d1947c3cf5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 15V, Positive-QTOF	splash10-014i-0090000000-20c9dc148a8a6b95bdd4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 90V, Positive-QTOF	splash10-0ac0-9300000000-ff095b41d66bc7c1c9b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metribuzin 30V, Positive-QTOF	splash10-014i-0190000000-1195477d789b2632ac33	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metribuzin 10V, Positive-QTOF	splash10-014i-0090000000-e13f332ff80b44342453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metribuzin 20V, Positive-QTOF	splash10-014i-3490000000-b250bde498ae6408d9f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metribuzin 40V, Positive-QTOF	splash10-006t-9200000000-4c4a499d8d26c485b02f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metribuzin 10V, Negative-QTOF	splash10-0006-0910000000-ba002331be1a9f61955a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metribuzin 20V, Negative-QTOF	splash10-074i-8930000000-8b90e1b9375076b8f5e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metribuzin 40V, Negative-QTOF	splash10-024i-9400000000-e42aee5a1db9176ccd85	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

C14332

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metribuzin

METLIN ID

Not Available

PubChem Compound

30479

PDB ID

Not Available

ChEBI ID

34846

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 Metribuzin (HMDB0254685)

MOL for HMDB0254685 (Metribuzin)

3D MOL for HMDB0254685 (Metribuzin)

3D SDF for HMDB0254685 (Metribuzin)

3D-SDF for HMDB0254685 (Metribuzin)

PDB for HMDB0254685 (Metribuzin)

3D PDB for HMDB0254685 (Metribuzin)

SMILES for HMDB0254685 (Metribuzin)

INCHI for HMDB0254685 (Metribuzin)

Structure for HMDB0254685 (Metribuzin)

3D Structure for HMDB0254685 (Metribuzin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra