Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:36:20 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240222

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thonzylamine

Description

Thonzylamine, also known as tonamil, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. In humans, thonzylamine is involved in the thonzylamine h1-antihistamine action pathway. Thonzylamine 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 Thonzylamine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0240222
     RDKit          3D
Thonzylamine
 43 44  0  0  0  0  0  0  0  0999 V2000
    6.2039   -1.6441    0.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9193   -1.5868    1.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -0.8780    0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -0.8265    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952   -0.1024    0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8056    0.5803   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7480    1.3473   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5913    1.0020   -0.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740   -0.3090   -0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.6093   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655   -1.9765   -0.8635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238   -2.2091   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0285   -2.9400   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    1.9920   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869    3.2380    0.2349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5907    4.2028    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859    3.9787    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214    2.7262    0.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    1.8085    0.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    0.5240   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -0.1980   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7820   -2.4627    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6868   -0.6697    0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307   -1.9390   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.3562    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.1060    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8453    1.2234   -2.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    2.4198   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -0.4215   -2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290   -1.1231   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.0244   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -0.5347    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136   -1.2695   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7707   -2.8973   -1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788   -2.6972    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963   -3.0426   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -2.6240    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -3.9084   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1572    5.1673    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826    4.7590    1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404    2.5380    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    1.0315   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0978   -0.2317   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

      
  Mrv1652311211718552D          

 21 22  0  0  0  0            999 V2000
    2.8579    0.8250    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
   -3.5724   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2374    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   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
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 C   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
   -2.8579    0.0000    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
    0.7145   -0.4125    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
    2.1434    1.2374    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
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  2  0  0  0  0
 10  4  1  0  0  0  0
 12 11  1  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 10  2  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21  3  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240222

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(CN(CCN(C)C)C2=NC=CC=N2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H22N4O/c1-19(2)11-12-20(16-17-9-4-10-18-16)13-14-5-7-15(21-3)8-6-14/h4-10H,11-13H2,1-3H3

> <INCHI_KEY>
GULNIHOSWFYMRN-UHFFFAOYSA-N

> <FORMULA>
C16H22N4O

> <MOLECULAR_WEIGHT>
286.379

> <EXACT_MASS>
286.179361344

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.416040275498986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.4220117106666663

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.618568624579826

> <JCHEM_POLAR_SURFACE_AREA>
41.49000000000001

> <JCHEM_REFRACTIVITY>
86.1918

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thonzylamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240222
     RDKit          3D
Thonzylamine
 43 44  0  0  0  0  0  0  0  0999 V2000
    6.2039   -1.6441    0.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9193   -1.5868    1.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -0.8780    0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -0.8265    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952   -0.1024    0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8056    0.5803   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7480    1.3473   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5913    1.0020   -0.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740   -0.3090   -0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.6093   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655   -1.9765   -0.8635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238   -2.2091   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0285   -2.9400   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    1.9920   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869    3.2380    0.2349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5907    4.2028    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859    3.9787    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214    2.7262    0.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    1.8085    0.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    0.5240   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -0.1980   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7820   -2.4627    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6868   -0.6697    0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307   -1.9390   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.3562    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.1060    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8453    1.2234   -2.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    2.4198   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -0.4215   -2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290   -1.1231   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.0244   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -0.5347    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136   -1.2695   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7707   -2.8973   -1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788   -2.6972    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963   -3.0426   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -2.6240    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -3.9084   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1572    5.1673    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826    4.7590    1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404    2.5380    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    1.0315   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0978   -0.2317   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   21                                                            
CONECT    4    9   10                                                       
CONECT    5    7   14                                                       
CONECT    6    8   14                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9    4   17                                                       
CONECT   10    4   18                                                       
CONECT   11   12   19                                                       
CONECT   12   11   20                                                       
CONECT   13   14   20                                                       
CONECT   14    5    6   13                                                  
CONECT   15    7    8   21                                                  
CONECT   16   17   18   20                                                  
CONECT   17    9   16                                                       
CONECT   18   10   16                                                       
CONECT   19    1    2   11                                                  
CONECT   20   12   13   16                                                  
CONECT   21    3   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0240222
HETATM    1  C1  UNL     1       6.204  -1.644   0.821  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.919  -1.587   1.399  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.884  -0.878   0.830  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.632  -0.826   1.400  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.595  -0.102   0.808  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.806   0.580  -0.367  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.748   1.347  -1.024  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.591   1.002  -0.658  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.074  -0.309  -0.942  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.471  -0.609  -0.525  1.00  0.00           C  
HETATM   11  N2  UNL     1      -2.866  -1.977  -0.863  1.00  0.00           N  
HETATM   12  C9  UNL     1      -4.224  -2.209  -0.438  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.028  -2.940  -0.170  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.389   1.992  -0.021  1.00  0.00           C  
HETATM   15  N3  UNL     1      -0.887   3.238   0.235  1.00  0.00           N  
HETATM   16  C12 UNL     1      -1.591   4.203   0.829  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.886   3.979   1.219  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.421   2.726   0.973  1.00  0.00           C  
HETATM   19  N4  UNL     1      -2.651   1.809   0.371  1.00  0.00           N  
HETATM   20  C15 UNL     1       3.062   0.524  -0.932  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.102  -0.198  -0.345  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.782  -2.463   1.301  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.687  -0.670   0.925  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.131  -1.939  -0.261  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.429  -1.356   2.332  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.649  -0.106   1.313  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.845   1.223  -2.135  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.924   2.420  -0.808  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.046  -0.422  -2.066  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.429  -1.123  -0.548  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.202   0.024  -1.068  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.535  -0.535   0.580  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.814  -1.269  -0.367  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.771  -2.897  -1.141  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.279  -2.697   0.568  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.096  -3.043  -0.725  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.909  -2.624   0.886  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.546  -3.908  -0.177  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.157   5.167   1.011  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.483   4.759   1.709  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.440   2.538   1.276  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.289   1.031  -1.842  1.00  0.00           H  
HETATM   43  H22 UNL     1       5.098  -0.232  -0.809  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   20
CONECT    7    8   27   28
CONECT    8    9   14
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   13
CONECT   12   33   34   35
CONECT   13   36   37   38
CONECT   14   15   15   19
CONECT   15   16
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   20   21   21   42
CONECT   21   43
END

HMDB0240222
     RDKit          3D
Thonzylamine
 43 44  0  0  0  0  0  0  0  0999 V2000
    6.2039   -1.6441    0.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9193   -1.5868    1.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -0.8780    0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -0.8265    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952   -0.1024    0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8056    0.5803   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7480    1.3473   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5913    1.0020   -0.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740   -0.3090   -0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.6093   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655   -1.9765   -0.8635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238   -2.2091   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0285   -2.9400   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    1.9920   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869    3.2380    0.2349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5907    4.2028    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859    3.9787    1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214    2.7262    0.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    1.8085    0.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    0.5240   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -0.1980   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7820   -2.4627    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6868   -0.6697    0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307   -1.9390   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.3562    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.1060    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8453    1.2234   -2.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    2.4198   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -0.4215   -2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290   -1.1231   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.0244   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -0.5347    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136   -1.2695   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7707   -2.8973   -1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788   -2.6972    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963   -3.0426   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -2.6240    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -3.9084   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1572    5.1673    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826    4.7590    1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404    2.5380    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    1.0315   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0978   -0.2317   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tonamil	Kegg
Neohetramine	HMDB, MeSH
Thonzylamine	HMDB
2-((2-(dimethylamino)Ethyl)(4-methoxybenzyl)amino)pyrimidine	MeSH, HMDB
Thonzylamine hydrochloride	MeSH, HMDB
Anahist	MeSH, HMDB
Histazylamine	MeSH, HMDB
Piristina	MeSH, HMDB
Resistab	MeSH, HMDB
Thonzylene	MeSH, HMDB
Ambistamin	MeSH, HMDB
Thonzylamine monohydrochloride	MeSH, HMDB

Chemical Formula

C₁₆H₂₂N₄O

Average Molecular Weight

286.379

Monoisotopic Molecular Weight

286.179361344

IUPAC Name

N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine

Traditional Name

thonzylamine

CAS Registry Number

91-85-0

SMILES

COC1=CC=C(CN(CCN(C)C)C2=NC=CC=N2)C=C1

InChI Identifier

InChI=1S/C16H22N4O/c1-19(2)11-12-20(16-17-9-4-10-18-16)13-14-5-7-15(21-3)8-6-14/h4-10H,11-13H2,1-3H3

InChI Key

GULNIHOSWFYMRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Benzylamine
Methoxybenzene
Dialkylarylamine
Alkyl aryl ether
Aminopyrimidine
Monocyclic benzene moiety
Pyrimidine
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240222)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Thonzylamine H1-Antihistamine Action (PathBank: SMP0058769)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	167.334	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000858

Predicted Molecular Properties

Property	Value	Source
logP	2.4	ALOGPS
logP	2.42	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	8.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.19 m³·mol⁻¹	ChemAxon
Polarizability	32.42 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
DarkChem	[M+H]+	167.795	31661259
DarkChem	[M-H]-	172.846	31661259
DeepCCS	[M+H]+	173.216	30932474
DeepCCS	[M-H]-	170.858	30932474
DeepCCS	[M-2H]-	203.744	30932474
DeepCCS	[M+Na]+	179.309	30932474
AllCCS	[M+H]+	168.7	32859911
AllCCS	[M+H-H2O]+	165.2	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	173.4	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	173.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.73 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1857 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	625.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	359.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	632.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	779.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	46.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	924.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	446.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	398.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	17.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thonzylamine	COC1=CC=C(CN(CCN(C)C)C2=NC=CC=N2)C=C1	3082.7	Standard polar	33892256
Thonzylamine	COC1=CC=C(CN(CCN(C)C)C2=NC=CC=N2)C=C1	2235.3	Standard non polar	33892256
Thonzylamine	COC1=CC=C(CN(CCN(C)C)C2=NC=CC=N2)C=C1	2193.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Thonzylamine EI-B (Non-derivatized)	splash10-05fr-9720000000-8a7d4d036feab1e4ee54	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thonzylamine EI-B (Non-derivatized)	splash10-05fr-9720000000-8a7d4d036feab1e4ee54	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thonzylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9450000000-72e6f4295340c602c154	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thonzylamine 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 - Thonzylamine 10V, Positive-QTOF	splash10-000i-0090000000-ca7acc0acee8c90c9ee1	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 20V, Positive-QTOF	splash10-00kf-1090000000-a3fcfc88d52e5058e5e2	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 40V, Positive-QTOF	splash10-006x-9640000000-a942ebc7240fba156991	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 10V, Negative-QTOF	splash10-000i-0090000000-822f872495fe6099d45e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 20V, Negative-QTOF	splash10-01p9-1290000000-1272fa384ec5fd19b77e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 40V, Negative-QTOF	splash10-0btd-3920000000-408e8d6d8b20a0c1db89	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 10V, Negative-QTOF	splash10-000i-0290000000-6e7a5ccb6d35446e2ee0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 20V, Negative-QTOF	splash10-01vo-3940000000-36a300465081f7c172dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 40V, Negative-QTOF	splash10-0a4m-2900000000-2376b8b46f16feeb464a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 10V, Positive-QTOF	splash10-000i-0090000000-b339c29b20510f7d0aaa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 20V, Positive-QTOF	splash10-00dr-4690000000-2c5717d3701b4eec6867	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thonzylamine 40V, Positive-QTOF	splash10-00di-7920000000-5631894acb184578eb97	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Thonzylamine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11235

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5258

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thonzylamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

ARMINIO JJ, SWEET CC: The prophylaxis and treatment of the common cold with neohetramine (thonzylamine hydrochloride). Ind Med Surg. 1949 Dec;18(12):509-11. [PubMed:15393969 ]

Showing metabocard for Thonzylamine (HMDB0240222)

MOL for HMDB0240222 (Thonzylamine)

3D MOL for HMDB0240222 (Thonzylamine)

3D SDF for HMDB0240222 (Thonzylamine)

3D-SDF for HMDB0240222 (Thonzylamine)

PDB for HMDB0240222 (Thonzylamine)

3D PDB for HMDB0240222 (Thonzylamine)

SMILES for HMDB0240222 (Thonzylamine)

INCHI for HMDB0240222 (Thonzylamine)

Structure for HMDB0240222 (Thonzylamine)

3D Structure for HMDB0240222 (Thonzylamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra