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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:50:15 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254501

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metamitron

Description

metamitron, also known as goltix, belongs to the class of organic compounds known as 1,2,4-triazines. 1,2,4-triazines are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 2, and 4. metamitron is a moderately basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Metamitron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metamitron 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

  Mrv1572004191602142D          

 15 16  0  0  0  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12  7  2  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254501

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NN=C(C(=O)N1N)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3

> <INCHI_KEY>
VHCNQEUWZYOAEV-UHFFFAOYSA-N

> <FORMULA>
C10H10N4O

> <MOLECULAR_WEIGHT>
202.217

> <EXACT_MASS>
202.085460958

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.48600444264922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-3-methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.44443946466666673

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.784857829121433

> <JCHEM_POLAR_SURFACE_AREA>
71.05

> <JCHEM_REFRACTIVITY>
56.64210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metamitron

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.002   9.240   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       4.001   8.470   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       6.668   8.470   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    1   12   14                                                  
CONECT    8    5    6    9                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   14   15                                                  
CONECT   11   14                                                            
CONECT   12    7   13                                                       
CONECT   13    9   12                                                       
CONECT   14    7   10   11                                                  
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Goltix	ChEBI
4-amino-3-Methyl-6-phenyl-1,2,4-triazin-5(4H)-one	MeSH
Metamitron	MeSH

Chemical Formula

C₁₀H₁₀N₄O

Average Molecular Weight

202.217

Monoisotopic Molecular Weight

202.085460958

IUPAC Name

4-amino-3-methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one

Traditional Name

metamitron

CAS Registry Number

Not Available

SMILES

CC1=NN=C(C(=O)N1N)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3

InChI Key

VHCNQEUWZYOAEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-triazines. 1,2,4-Triazines are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 2, and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazines

Sub Class

1,2,4-triazines

Direct Parent

1,2,4-triazines

Alternative Parents

Substituents

1,2,4-triazine
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,2,4-triazines (CHEBI:6791 )
Triazinone herbicides (C10930 )

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	1.17	ALOGPS
logP	0.44	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	2.78	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	1	ChemAxon
Refractivity	56.64 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	2	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]+	141.207	30932474
DeepCCS	[M-H]-	138.811	30932474
DeepCCS	[M-2H]-	172.554	30932474
DeepCCS	[M+Na]+	147.224	30932474
AllCCS	[M+H]+	144.4	32859911
AllCCS	[M+H-H2O]+	140.1	32859911
AllCCS	[M+NH4]+	148.5	32859911
AllCCS	[M+Na]+	149.6	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	145.8	32859911
AllCCS	[M+HCOO]-	146.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
METAMITRON	CC1=NN=C(C(=O)N1N)C1=CC=CC=C1	3018.1	Standard polar	33892256
METAMITRON	CC1=NN=C(C(=O)N1N)C1=CC=CC=C1	2046.9	Standard non polar	33892256
METAMITRON	CC1=NN=C(C(=O)N1N)C1=CC=CC=C1	2208.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
METAMITRON,1TMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N[Si](C)(C)C	2043.9	Semi standard non polar	33892256
METAMITRON,1TMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N[Si](C)(C)C	1981.6	Standard non polar	33892256
METAMITRON,1TMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N[Si](C)(C)C	3050.5	Standard polar	33892256
METAMITRON,2TMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N([Si](C)(C)C)[Si](C)(C)C	1976.5	Semi standard non polar	33892256
METAMITRON,2TMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N([Si](C)(C)C)[Si](C)(C)C	2127.5	Standard non polar	33892256
METAMITRON,2TMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N([Si](C)(C)C)[Si](C)(C)C	2596.4	Standard polar	33892256
METAMITRON,1TBDMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N[Si](C)(C)C(C)(C)C	2263.8	Semi standard non polar	33892256
METAMITRON,1TBDMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N[Si](C)(C)C(C)(C)C	2180.0	Standard non polar	33892256
METAMITRON,1TBDMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N[Si](C)(C)C(C)(C)C	3155.5	Standard polar	33892256
METAMITRON,2TBDMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2414.6	Semi standard non polar	33892256
METAMITRON,2TBDMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2502.9	Standard non polar	33892256
METAMITRON,2TBDMS,isomer #1	CC1=NN=C(C2=CC=CC=C2)C(=O)N1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2769.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metamitron GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1910000000-91c360b3b27bc03cc61c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metamitron 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 - Metamitron 90V, Positive-QTOF	splash10-0udi-9700000000-9eb48288467d9eddb4cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 75V, Positive-QTOF	splash10-0udi-8900000000-63f720cec23c7cddd370	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 60V, Positive-QTOF	splash10-0fb9-1910000000-80e4d57dfa1f5af9b375	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 75V, Positive-QTOF	splash10-0ufr-2900000000-c3b4f504834e4f8d847a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 90V, Negative-QTOF	splash10-014i-0900000000-65eec74b93e245378edf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 45V, Positive-QTOF	splash10-0ufr-0890000000-fd6dc5f315513eeb0214	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 30V, Positive-QTOF	splash10-0udi-0090000000-e82fd85b4744362799c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 60V, Negative-QTOF	splash10-014i-0900000000-1ff0a9cca1f6ef77b132	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 60V, Positive-QTOF	splash10-0fb9-1910000000-b97cdd92a98c8e118d1f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 75V, Positive-QTOF	splash10-0ufr-2900000000-6e6dc62fdb9ee675fd53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 15V, Positive-QTOF	splash10-0udi-0090000000-346d503aa5e3bd5ac64e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 15V, Positive-QTOF	splash10-0udi-0090000000-b9918411adbcc397ab90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 35V, Positive-QTOF	splash10-00b9-0900000000-9c499740aceffd050e9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 90V, Positive-QTOF	splash10-0udi-3900000000-328c6097489c8eceeab2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 55V, Positive-QTOF	splash10-00b9-0900000000-6b0236661c3cfe60299d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 35V, Positive-QTOF	splash10-0udi-0970000000-070d19942ed492e1133f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 30V, Positive-QTOF	splash10-0udi-0090000000-ac423251b639ac7606b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 55V, Positive-QTOF	splash10-0fb9-0920000000-5b1c07fdc880d70a8234	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metamitron 80V, Positive-QTOF	splash10-0udi-2900000000-2bc7f6d54a1c7e8d37e2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamitron 10V, Positive-QTOF	splash10-0udi-0090000000-90a1dcea7e5848b5f534	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamitron 20V, Positive-QTOF	splash10-0udi-1490000000-05adedcb342d6e3a4c47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamitron 40V, Positive-QTOF	splash10-0006-9600000000-b1c03b237e41c4f69a5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamitron 10V, Negative-QTOF	splash10-0udi-0390000000-3c931afcd8470f426836	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamitron 20V, Negative-QTOF	splash10-00di-1900000000-2e72070420310cb85845	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamitron 40V, Negative-QTOF	splash10-066u-6900000000-435e0590d8b66386aa2d	2016-08-04	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

C10930

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38854

PDB ID

Not Available

ChEBI ID

6791

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 Metamitron (HMDB0254501)

MOL for HMDB0254501 (Metamitron)

3D MOL for HMDB0254501 (Metamitron)

3D SDF for HMDB0254501 (Metamitron)

3D-SDF for HMDB0254501 (Metamitron)

PDB for HMDB0254501 (Metamitron)

3D PDB for HMDB0254501 (Metamitron)

SMILES for HMDB0254501 (Metamitron)

INCHI for HMDB0254501 (Metamitron)

Structure for HMDB0254501 (Metamitron)

3D Structure for HMDB0254501 (Metamitron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra