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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:38:12 UTC

Update Date

2022-09-22 18:35:06 UTC

HMDB ID

HMDB0341197

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Simeton

Description

simeton, also known as methoxy simazine, belongs to the class of organic compounds known as 2-methoxy-1,3,5-triazines. These are aromatic heterocyclic compounds containing a 1,3,5-triazine ring, which is substituted at the 2-position with a methoxy group. simeton is a very strong basic compound (based on its pKa). A methoxy-1,3,5-triazine that is 6-methoxy-1,3,5-triazine-2,4-diamine in which one of the hydrogens of each amino group has been replaced by an ethyl group.

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004251603042D          

 14 14  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  9  4  1  4  0  0  0
  9  6  2  0  0  0  0
 10  5  1  4  0  0  0
 10  7  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341197

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN=C1NC(OC)=NC(N1)=NCC

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N5O/c1-4-9-6-11-7(10-5-2)13-8(12-6)14-3/h4-5H2,1-3H3,(H2,9,10,11,12,13)

> <INCHI_KEY>
HKAMKLBXTLTVCN-UHFFFAOYSA-N

> <FORMULA>
C8H15N5O

> <MOLECULAR_WEIGHT>
197.242

> <EXACT_MASS>
197.127660123

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.528820752354214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[6-(ethylimino)-4-methoxy-1,2,5,6-tetrahydro-1,3,5-triazin-2-ylidene]ethan-1-amine

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
0.6876255188126759

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.211142250875724

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.221526051931717

> <JCHEM_PKA_STRONGEST_BASIC>
6.705825058753886

> <JCHEM_POLAR_SURFACE_AREA>
70.37

> <JCHEM_REFRACTIVITY>
53.4055

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[4-(ethylimino)-6-methoxy-3,5-dihydro-1,3,5-triazin-2-ylidene]ethanamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   14                                                            
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    9   11   12                                                  
CONECT    7   10   11   13                                                  
CONECT    8   12   13   14                                                  
CONECT    9    4    6                                                       
CONECT   10    5    7                                                       
CONECT   11    6    7                                                       
CONECT   12    6    8                                                       
CONECT   13    7    8                                                       
CONECT   14    3    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4-Bis(ethylamino)-6-methoxy-S-triazine	ChEBI
2-Methoxy-4,6-bis(ethylamino)-1,3,5-triazine	ChEBI
4,6-Bis(ethylamino)-2-methoxy-S-triazine	ChEBI
Methoxy simazine	ChEBI
Simeton	MeSH
2-Methoxy-4-ethylamino-6-ethylamino-1,3,5-triazine	MeSH

Chemical Formula

C₈H₁₅N₅O

Average Molecular Weight

197.242

Monoisotopic Molecular Weight

197.127660123

IUPAC Name

N-[6-(ethylimino)-4-methoxy-1,2,5,6-tetrahydro-1,3,5-triazin-2-ylidene]ethan-1-amine

Traditional Name

N-[4-(ethylimino)-6-methoxy-3,5-dihydro-1,3,5-triazin-2-ylidene]ethanamine

CAS Registry Number

Not Available

SMILES

CCN=C1NC(OC)=NC(N1)=NCC

InChI Identifier

InChI=1S/C8H15N5O/c1-4-9-6-11-7(10-5-2)13-8(12-6)14-3/h4-5H2,1-3H3,(H2,9,10,11,12,13)

InChI Key

HKAMKLBXTLTVCN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-methoxy-1,3,5-triazines. These are aromatic heterocyclic compounds containing a 1,3,5-triazine ring, which is substituted at the 2-position with a methoxy group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazines

Sub Class

1,3,5-triazines

Direct Parent

2-methoxy-1,3,5-triazines

Alternative Parents

Substituents

2-methoxy-1,3,5-triazine
Alkyl aryl ether
Heteroaromatic compound
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

diamino-1,3,5-triazine (CHEBI:30264 )
methoxy-1,3,5-triazine (CHEBI:30264 )

Ontology

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	0.14	ALOGPS
logP	0.69	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	6.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.41 m³·mol⁻¹	ChemAxon
Polarizability	21.53 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 Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simeton 10V, Positive-QTOF	splash10-0002-0900000000-c79b3c40c15cbecf1f73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simeton 20V, Positive-QTOF	splash10-00xs-1900000000-2a3786522eeb5678ea02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simeton 40V, Positive-QTOF	splash10-0096-9700000000-a8063f38bb652da751e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simeton 10V, Negative-QTOF	splash10-0002-1900000000-36f9ded0e6844084618b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simeton 20V, Negative-QTOF	splash10-0aov-9700000000-0a534d3130d125f9b86c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simeton 40V, Negative-QTOF	splash10-0a4i-9300000000-88f3147377bd80ad0457	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	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

12654

PDB ID

Not Available

ChEBI ID

30264

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

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for Simeton (HMDB0341197)

MOL for HMDB0341197 (Simeton)

3D MOL for HMDB0341197 (Simeton)

3D SDF for HMDB0341197 (Simeton)

3D-SDF for HMDB0341197 (Simeton)

PDB for HMDB0341197 (Simeton)

3D PDB for HMDB0341197 (Simeton)

SMILES for HMDB0341197 (Simeton)

INCHI for HMDB0341197 (Simeton)

Structure for HMDB0341197 (Simeton)

3D Structure for HMDB0341197 (Simeton)

Predicted Kovats Retention Indices

MS/MS Spectra