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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:40:49 UTC

Update Date

2021-09-26 23:16:36 UTC

HMDB ID

HMDB0259195

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Triethylenemelamine

Description

tretamine, also known as TEM, belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. tretamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on tretamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Triethylenemelamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Triethylenemelamine 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


  Mrv1533004241523292D          

 15 18  0  0  0  0            999 V2000
    1.1270   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259195

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CN1C1=NC(=NC(=N1)N1CC1)N1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12N6/c1-2-13(1)7-10-8(14-3-4-14)12-9(11-7)15-5-6-15/h1-6H2

> <INCHI_KEY>
IUCJMVBFZDHPDX-UHFFFAOYSA-N

> <FORMULA>
C9H12N6

> <MOLECULAR_WEIGHT>
204.237

> <EXACT_MASS>
204.11234441

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.071763766144123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tris(aziridin-1-yl)-1,3,5-triazine

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.7016468289999993

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.479887709899162

> <JCHEM_POLAR_SURFACE_AREA>
47.93

> <JCHEM_REFRACTIVITY>
59.73840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triethylenemelamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.104  -3.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -3.644   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.771   3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.541   2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -2.874   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.104   3.644   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    3                                                       
CONECT    3    2    1    4                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10                                                       
CONECT   13    6   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   36    0
END

COMPND    HMDB0259195
HETATM    1  C1  UNL     1       0.571   3.185   2.539  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.900   2.980   1.968  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.720   2.123   1.592  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.343   1.022   0.769  1.00  0.00           C  
HETATM    5  N2  UNL     1      -0.932   0.579   0.776  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.331  -0.456   0.016  1.00  0.00           C  
HETATM    7  N3  UNL     1      -2.688  -0.869   0.073  1.00  0.00           N  
HETATM    8  C5  UNL     1      -3.724  -1.765  -0.378  1.00  0.00           C  
HETATM    9  C6  UNL     1      -4.036  -0.704   0.618  1.00  0.00           C  
HETATM   10  N4  UNL     1      -0.443  -1.091  -0.791  1.00  0.00           N  
HETATM   11  C7  UNL     1       0.826  -0.663  -0.809  1.00  0.00           C  
HETATM   12  N5  UNL     1       1.781  -1.301  -1.638  1.00  0.00           N  
HETATM   13  C8  UNL     1       2.258  -2.272  -2.608  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.211  -1.326  -2.088  1.00  0.00           C  
HETATM   15  N6  UNL     1       1.190   0.374  -0.036  1.00  0.00           N  
HETATM   16  H1  UNL     1      -0.019   4.049   2.158  1.00  0.00           H  
HETATM   17  H2  UNL     1       0.451   2.939   3.627  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.298   3.611   1.144  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.666   2.365   2.471  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.764  -2.806   0.031  1.00  0.00           H  
HETATM   21  H6  UNL     1      -4.142  -1.654  -1.401  1.00  0.00           H  
HETATM   22  H7  UNL     1      -4.636   0.150   0.256  1.00  0.00           H  
HETATM   23  H8  UNL     1      -4.208  -0.962   1.678  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.920  -2.203  -3.655  1.00  0.00           H  
HETATM   25  H10 UNL     1       2.333  -3.333  -2.243  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.490  -0.461  -2.754  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.964  -1.511  -1.317  1.00  0.00           H  
CONECT    1    2    3   16   17
CONECT    2    3   18   19
CONECT    3    4
CONECT    4    5    5   15
CONECT    5    6
CONECT    6    7   10   10
CONECT    7    8    9
CONECT    8    9   20   21
CONECT    9   22   23
CONECT   10   11
CONECT   11   12   15   15
CONECT   12   13   14
CONECT   13   14   24   25
CONECT   14   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4,6-Tri(1-aziridinyl)-1,3,5-triazine	ChEBI
2,4,6-Tris(1-aziridinyl)-1,3,5-triazine	ChEBI
2,4,6-Tris(1-aziridinyl)-S-triazine	ChEBI
2,4,6-Tris(aziridin-1-yl)-1,3,5-triazine	ChEBI
TEM	ChEBI
Triethylenemelamine	ChEBI
Trisaziridinyltriazine	ChEBI
2,4,6-Triethylimino-1,3,5-triazine	MeSH
Melamine, triethylene	MeSH
Tretamine	MeSH
Triethylene melamine	MeSH

Chemical Formula

C₉H₁₂N₆

Average Molecular Weight

204.237

Monoisotopic Molecular Weight

204.11234441

IUPAC Name

tris(aziridin-1-yl)-1,3,5-triazine

Traditional Name

triethylenemelamine

CAS Registry Number

Not Available

SMILES

C1CN1C1=NC(=NC(=N1)N1CC1)N1CC1

InChI Identifier

InChI=1S/C9H12N6/c1-2-13(1)7-10-8(14-3-4-14)12-9(11-7)15-5-6-15/h1-6H2

InChI Key

IUCJMVBFZDHPDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Dialkylarylamine
Aminotriazine
Amino-1,3,5-triazine
1,3,5-triazine
Triazine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Aziridine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3,5-triazines (CHEBI:27919 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	1.08	ALOGPS
logP	1.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	7.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.74 m³·mol⁻¹	ChemAxon
Polarizability	21.07 Å³	ChemAxon
Number of Rings	4	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]+	146.738	30932474
DeepCCS	[M-H]-	144.342	30932474
DeepCCS	[M-2H]-	177.86	30932474
DeepCCS	[M+Na]+	152.65	30932474
AllCCS	[M+H]+	146.5	32859911
AllCCS	[M+H-H2O]+	142.4	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.4	32859911
AllCCS	[M-H]-	146.5	32859911
AllCCS	[M+Na-2H]-	146.2	32859911
AllCCS	[M+HCOO]-	145.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Triethylenemelamine	C1CN1C1=NC(=NC(=N1)N1CC1)N1CC1	2326.6	Standard polar	33892256
Triethylenemelamine	C1CN1C1=NC(=NC(=N1)N1CC1)N1CC1	1980.9	Standard non polar	33892256
Triethylenemelamine	C1CN1C1=NC(=NC(=N1)N1CC1)N1CC1	2152.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylenemelamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-9850000000-45216a053b2b87556885	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylenemelamine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylenemelamine 10V, Positive-QTOF	splash10-0a4i-0090000000-b7efb51b8e9774e0c766	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylenemelamine 20V, Positive-QTOF	splash10-0a4i-1190000000-f5e44a9bec405784ad70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylenemelamine 40V, Positive-QTOF	splash10-0296-7900000000-892fa3a2c45b88f8e1f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylenemelamine 10V, Negative-QTOF	splash10-0udi-0090000000-08dfbdfba72e42edef0d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylenemelamine 20V, Negative-QTOF	splash10-0udi-2490000000-2feabbcd3b14b8520433	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylenemelamine 40V, Negative-QTOF	splash10-070t-2900000000-63e8e1d580e56110ab40	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	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

C00013159

Chemspider ID

5594

KEGG Compound ID

C07642

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triethylenemelamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27919

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 Triethylenemelamine (HMDB0259195)

MOL for HMDB0259195 (Triethylenemelamine)

3D MOL for HMDB0259195 (Triethylenemelamine)

3D SDF for HMDB0259195 (Triethylenemelamine)

3D-SDF for HMDB0259195 (Triethylenemelamine)

PDB for HMDB0259195 (Triethylenemelamine)

3D PDB for HMDB0259195 (Triethylenemelamine)

SMILES for HMDB0259195 (Triethylenemelamine)

INCHI for HMDB0259195 (Triethylenemelamine)

Structure for HMDB0259195 (Triethylenemelamine)

3D Structure for HMDB0259195 (Triethylenemelamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra