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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:00:25 UTC

Update Date

2021-09-26 23:16:23 UTC

HMDB ID

HMDB0259069

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tiapamil

Description

Tiapamil, also known as dimeditiapramine, belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. Based on a literature review a significant number of articles have been published on Tiapamil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tiapamil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tiapamil 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


  Mrv1652309112123002D          

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M  END

HMDB0259069
     RDKit          3D
Tiapamil
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M  END


  Mrv1652309112123002D          

 37 39  0  0  0  0            999 V2000
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 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259069

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(CCN(C)CCCC2(C3=CC(OC)=C(OC)C=C3)S(=O)(=O)CCCS2(=O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO8S2/c1-27(15-12-20-8-10-22(32-2)24(18-20)34-4)14-6-13-26(36(28,29)16-7-17-37(26,30)31)21-9-11-23(33-3)25(19-21)35-5/h8-11,18-19H,6-7,12-17H2,1-5H3

> <INCHI_KEY>
ZROUQTNYPCANTN-UHFFFAOYSA-N

> <FORMULA>
C26H37NO8S2

> <MOLECULAR_WEIGHT>
555.7

> <EXACT_MASS>
555.196059503

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
58.60158065455866

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-2-(3-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}propyl)-1lambda6,3lambda6-dithiane-1,1,3,3-tetrone

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.3668529906666684

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.876319414015398

> <JCHEM_POLAR_SURFACE_AREA>
108.44000000000003

> <JCHEM_REFRACTIVITY>
143.64709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dimethoxyphenyl)-2-(3-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}propyl)-1lambda6,3lambda6-dithiane-1,1,3,3-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259069
     RDKit          3D
Tiapamil
 74 76  0  0  0  0  0  0  0  0999 V2000
   -8.5143    0.6504   -1.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9677   -0.1038   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7510    0.2833   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1092    1.3746   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9227    1.8008   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3391    1.1264    0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273    1.5866    1.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757    0.5091    1.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487   -0.5782    1.1688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839   -1.4629    2.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134   -0.6775   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3306    0.0624   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -0.4086   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1945    0.1847   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571   -0.4132    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2644   -1.1681    1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161   -1.6937    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -1.4643    1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -1.9457    1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629   -2.6964    2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7260   -0.6841    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9795   -0.4667   -0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417    0.3030   -1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6257   -0.1762   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4045   -0.4436   -2.3498 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.6407   -1.3431   -2.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2716   -1.3576   -2.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337    0.7932   -3.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    2.1035   -3.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6753    2.7795   -2.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207    1.9298   -0.5642 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.3803    2.2852    0.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624    2.5819   -0.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682    0.0222    1.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1697   -0.4103    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8707   -1.5274    1.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4329   -2.3617    2.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7176    1.6923   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5022    0.2161   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8696    0.7314   -2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5707    1.9076   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4207    2.6682   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    2.2927    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5241    2.2449    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    0.9948    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    0.0950    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570   -0.7968    2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896   -2.0682    2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237   -2.1514    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770   -1.7949   -0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.4507   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -0.0635   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    1.1262   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877   -0.1519    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -1.5090   -0.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940   -1.3619    1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632   -2.2827    2.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -2.3489    3.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0534   -2.6913    3.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2227   -3.7784    2.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2118    0.6654   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    1.2327   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8728   -0.2611   -2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912    0.4315   -1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    1.0168   -3.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934    0.4532   -4.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    1.8444   -2.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802    2.7061   -4.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    2.8941   -2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    3.8134   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -0.5067    2.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1777   -2.7067    3.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -1.9661    2.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0155   -3.3002    1.8793 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 14 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  2  0
  6 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  1  0
 35  3  1  0
 31 14  1  0
 24 15  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 16 56  1  0
 17 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 28 65  1  0
 28 66  1  0
 29 67  1  0
 29 68  1  0
 30 69  1  0
 30 70  1  0
 34 71  1  0
 37 72  1  0
 37 73  1  0
 37 74  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.668  -6.930   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       0.344  -5.750   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       1.677  -4.980   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.183  -4.303   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.173  -6.018   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.700  -7.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.710  -8.645   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0       0.807  -8.377   0.000  0.00  0.00           S+0
HETATM   14  O   UNK     0       1.127  -9.883   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.235  -8.954   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.324  -5.750   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.797  -4.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.787  -3.123   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.303  -3.391   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.830  -4.838   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.840  -6.018   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.293  -2.211   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.810  -2.479   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.260  -1.676   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.250  -0.497   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13   16                                             
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23                                                       
CONECT   23   22                                                            
CONECT   24   18   25                                                       
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31   35                                                       
CONECT   35   34                                                            
CONECT   36   30   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

COMPND    HMDB0259069
HETATM    1  C1  UNL     1      -8.514   0.650  -1.775  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.968  -0.104  -0.721  1.00  0.00           O  
HETATM    3  C2  UNL     1      -6.751   0.283  -0.183  1.00  0.00           C  
HETATM    4  C3  UNL     1      -6.109   1.375  -0.706  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.923   1.801  -0.213  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.339   1.126   0.847  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.027   1.587   1.375  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.176   0.509   1.885  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.749  -0.578   1.169  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.984  -1.463   2.031  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.513  -0.678  -0.177  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.331   0.062  -0.783  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.931  -0.409  -0.162  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.194   0.185  -0.694  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.357  -0.413   0.065  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.264  -1.168   1.205  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.416  -1.694   1.816  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.647  -1.464   1.286  1.00  0.00           C  
HETATM   19  O2  UNL     1       6.793  -1.946   1.840  1.00  0.00           O  
HETATM   20  C17 UNL     1       6.963  -2.696   2.972  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.726  -0.684   0.111  1.00  0.00           C  
HETATM   22  O3  UNL     1       6.980  -0.467  -0.397  1.00  0.00           O  
HETATM   23  C19 UNL     1       7.142   0.303  -1.555  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.626  -0.176  -0.479  1.00  0.00           C  
HETATM   25  S1  UNL     1       2.404  -0.444  -2.350  1.00  0.00           S  
HETATM   26  O4  UNL     1       3.641  -1.343  -2.398  1.00  0.00           O  
HETATM   27  O5  UNL     1       1.272  -1.358  -2.734  1.00  0.00           O  
HETATM   28  C21 UNL     1       2.634   0.793  -3.559  1.00  0.00           C  
HETATM   29  C22 UNL     1       1.967   2.104  -3.200  1.00  0.00           C  
HETATM   30  C23 UNL     1       2.675   2.780  -2.059  1.00  0.00           C  
HETATM   31  S2  UNL     1       2.321   1.930  -0.564  1.00  0.00           S  
HETATM   32  O6  UNL     1       3.380   2.285   0.487  1.00  0.00           O  
HETATM   33  O7  UNL     1       1.062   2.582  -0.001  1.00  0.00           O  
HETATM   34  C24 UNL     1      -4.968   0.022   1.388  1.00  0.00           C  
HETATM   35  C25 UNL     1      -6.170  -0.410   0.884  1.00  0.00           C  
HETATM   36  O8  UNL     1      -6.871  -1.527   1.360  1.00  0.00           O  
HETATM   37  C26 UNL     1      -6.433  -2.362   2.384  1.00  0.00           C  
HETATM   38  H1  UNL     1      -8.718   1.692  -1.444  1.00  0.00           H  
HETATM   39  H2  UNL     1      -9.502   0.216  -2.068  1.00  0.00           H  
HETATM   40  H3  UNL     1      -7.870   0.731  -2.665  1.00  0.00           H  
HETATM   41  H4  UNL     1      -6.571   1.908  -1.533  1.00  0.00           H  
HETATM   42  H5  UNL     1      -4.421   2.668  -0.639  1.00  0.00           H  
HETATM   43  H6  UNL     1      -3.247   2.293   2.239  1.00  0.00           H  
HETATM   44  H7  UNL     1      -2.524   2.245   0.616  1.00  0.00           H  
HETATM   45  H8  UNL     1      -1.287   0.995   2.474  1.00  0.00           H  
HETATM   46  H9  UNL     1      -2.738   0.095   2.816  1.00  0.00           H  
HETATM   47  H10 UNL     1      -0.457  -0.797   2.779  1.00  0.00           H  
HETATM   48  H11 UNL     1      -1.690  -2.068   2.678  1.00  0.00           H  
HETATM   49  H12 UNL     1      -0.324  -2.151   1.525  1.00  0.00           H  
HETATM   50  H13 UNL     1      -1.377  -1.795  -0.419  1.00  0.00           H  
HETATM   51  H14 UNL     1      -2.444  -0.451  -0.806  1.00  0.00           H  
HETATM   52  H15 UNL     1      -0.356  -0.063  -1.896  1.00  0.00           H  
HETATM   53  H16 UNL     1      -0.511   1.126  -0.536  1.00  0.00           H  
HETATM   54  H17 UNL     1       0.888  -0.152   0.930  1.00  0.00           H  
HETATM   55  H18 UNL     1       1.016  -1.509  -0.310  1.00  0.00           H  
HETATM   56  H19 UNL     1       2.294  -1.362   1.642  1.00  0.00           H  
HETATM   57  H20 UNL     1       4.263  -2.283   2.717  1.00  0.00           H  
HETATM   58  H21 UNL     1       7.858  -2.349   3.581  1.00  0.00           H  
HETATM   59  H22 UNL     1       6.053  -2.691   3.592  1.00  0.00           H  
HETATM   60  H23 UNL     1       7.223  -3.778   2.769  1.00  0.00           H  
HETATM   61  H24 UNL     1       8.212   0.665  -1.630  1.00  0.00           H  
HETATM   62  H25 UNL     1       6.525   1.233  -1.554  1.00  0.00           H  
HETATM   63  H26 UNL     1       6.873  -0.261  -2.448  1.00  0.00           H  
HETATM   64  H27 UNL     1       4.691   0.432  -1.388  1.00  0.00           H  
HETATM   65  H28 UNL     1       3.707   1.017  -3.789  1.00  0.00           H  
HETATM   66  H29 UNL     1       2.193   0.453  -4.515  1.00  0.00           H  
HETATM   67  H30 UNL     1       0.951   1.844  -2.875  1.00  0.00           H  
HETATM   68  H31 UNL     1       1.980   2.706  -4.123  1.00  0.00           H  
HETATM   69  H32 UNL     1       3.767   2.894  -2.245  1.00  0.00           H  
HETATM   70  H33 UNL     1       2.284   3.813  -1.990  1.00  0.00           H  
HETATM   71  H34 UNL     1      -4.528  -0.507   2.202  1.00  0.00           H  
HETATM   72  H35 UNL     1      -7.178  -2.707   3.092  1.00  0.00           H  
HETATM   73  H36 UNL     1      -5.591  -1.966   2.949  1.00  0.00           H  
HETATM   74  H37 UNL     1      -6.015  -3.300   1.879  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3
CONECT    3    4    4   35
CONECT    4    5   41
CONECT    5    6    6   42
CONECT    6    7   34
CONECT    7    8   43   44
CONECT    8    9   45   46
CONECT    9   10   11
CONECT   10   47   48   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   54   55
CONECT   14   15   25   31
CONECT   15   16   16   24
CONECT   16   17   56
CONECT   17   18   18   57
CONECT   18   19   21
CONECT   19   20
CONECT   20   58   59   60
CONECT   21   22   24   24
CONECT   22   23
CONECT   23   61   62   63
CONECT   24   64
CONECT   25   26   26   27   27
CONECT   25   28
CONECT   28   29   65   66
CONECT   29   30   67   68
CONECT   30   31   69   70
CONECT   31   32   32   33   33
CONECT   34   35   35   71
CONECT   35   36
CONECT   36   37
CONECT   37   72   73   74
END

HMDB0259069
     RDKit          3D
Tiapamil
 74 76  0  0  0  0  0  0  0  0999 V2000
   -8.5143    0.6504   -1.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9677   -0.1038   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7510    0.2833   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1092    1.3746   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9227    1.8008   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3391    1.1264    0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273    1.5866    1.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757    0.5091    1.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487   -0.5782    1.1688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839   -1.4629    2.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134   -0.6775   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3306    0.0624   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -0.4086   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1945    0.1847   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571   -0.4132    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2644   -1.1681    1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161   -1.6937    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -1.4643    1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -1.9457    1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629   -2.6964    2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7260   -0.6841    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9795   -0.4667   -0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417    0.3030   -1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6257   -0.1762   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4045   -0.4436   -2.3498 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.6407   -1.3431   -2.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2716   -1.3576   -2.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337    0.7932   -3.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    2.1035   -3.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6753    2.7795   -2.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207    1.9298   -0.5642 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.3803    2.2852    0.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624    2.5819   -0.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682    0.0222    1.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1697   -0.4103    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8707   -1.5274    1.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4329   -2.3617    2.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7176    1.6923   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5022    0.2161   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8696    0.7314   -2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5707    1.9076   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4207    2.6682   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    2.2927    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5241    2.2449    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    0.9948    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    0.0950    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570   -0.7968    2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896   -2.0682    2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237   -2.1514    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770   -1.7949   -0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.4507   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -0.0635   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    1.1262   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877   -0.1519    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -1.5090   -0.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940   -1.3619    1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632   -2.2827    2.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -2.3489    3.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0534   -2.6913    3.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2227   -3.7784    2.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2118    0.6654   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    1.2327   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8728   -0.2611   -2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912    0.4315   -1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    1.0168   -3.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934    0.4532   -4.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    1.8444   -2.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802    2.7061   -4.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    2.8941   -2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    3.8134   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -0.5067    2.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1777   -2.7067    3.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -1.9661    2.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0155   -3.3002    1.8793 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 14 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  2  0
  6 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  1  0
 35  3  1  0
 31 14  1  0
 24 15  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 16 56  1  0
 17 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 28 65  1  0
 28 66  1  0
 29 67  1  0
 29 68  1  0
 30 69  1  0
 30 70  1  0
 34 71  1  0
 37 72  1  0
 37 73  1  0
 37 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dimeditiapramine hydrochloride	HMDB
Hydrochloride, dimeditiapramine	HMDB
Hydrochloride, tiapamil	HMDB
N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithian-2-propylamin-1,1,3,3-tetroxide hydrochloride	HMDB
Tiapamil hydrochloride	HMDB
Dimeditiapramine	HMDB

Chemical Formula

C₂₆H₃₇NO₈S₂

Average Molecular Weight

555.7

Monoisotopic Molecular Weight

555.196059503

IUPAC Name

2-(3,4-dimethoxyphenyl)-2-(3-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}propyl)-1lambda6,3lambda6-dithiane-1,1,3,3-tetrone

Traditional Name

2-(3,4-dimethoxyphenyl)-2-(3-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}propyl)-1lambda6,3lambda6-dithiane-1,1,3,3-tetrone

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(CCN(C)CCCC2(C3=CC(OC)=C(OC)C=C3)S(=O)(=O)CCCS2(=O)=O)C=C1

InChI Identifier

InChI=1S/C26H37NO8S2/c1-27(15-12-20-8-10-22(32-2)24(18-20)34-4)14-6-13-26(36(28,29)16-7-17-37(26,30)31)21-9-11-23(33-3)25(19-21)35-5/h8-11,18-19H,6-7,12-17H2,1-5H3

InChI Key

ZROUQTNYPCANTN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
O-dimethoxybenzene
Dimethoxybenzene
Phenethylamine
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Dithioketal
Aralkylamine
1,3-dithiane
Sulfone
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic amino compound (CHEBI:35016 )
benzenes (CHEBI:35016 )

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	2.65	ALOGPS
logP	2.37	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	6.88	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	108.44 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	143.65 m³·mol⁻¹	ChemAxon
Polarizability	58.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	218.255	30932474
DeepCCS	[M-H]-	215.86	30932474
DeepCCS	[M-2H]-	248.742	30932474
DeepCCS	[M+Na]+	224.849	30932474
AllCCS	[M+H]+	225.3	32859911
AllCCS	[M+H-H2O]+	223.8	32859911
AllCCS	[M+NH4]+	226.7	32859911
AllCCS	[M+Na]+	227.1	32859911
AllCCS	[M-H]-	220.0	32859911
AllCCS	[M+Na-2H]-	222.2	32859911
AllCCS	[M+HCOO]-	224.9	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.	5.45 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9518 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1991.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	182.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	322.4 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	385.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	706.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	905.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	367.7 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	1289.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	395.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	413.6 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	9.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tiapamil	COC1=C(OC)C=C(CCN(C)CCCC2(C3=CC(OC)=C(OC)C=C3)S(=O)(=O)CCCS2(=O)=O)C=C1	6167.5	Standard polar	33892256
Tiapamil	COC1=C(OC)C=C(CCN(C)CCCC2(C3=CC(OC)=C(OC)C=C3)S(=O)(=O)CCCS2(=O)=O)C=C1	4287.8	Standard non polar	33892256
Tiapamil	COC1=C(OC)C=C(CCN(C)CCCC2(C3=CC(OC)=C(OC)C=C3)S(=O)(=O)CCCS2(=O)=O)C=C1	4091.1	Semi standard non polar	33892256

Spectra

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

38399

KEGG Compound ID

C13765

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tiapamil

METLIN ID

Not Available

PubChem Compound

42107

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

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 Tiapamil (HMDB0259069)

MOL for HMDB0259069 (Tiapamil)

3D MOL for HMDB0259069 (Tiapamil)

3D SDF for HMDB0259069 (Tiapamil)

3D-SDF for HMDB0259069 (Tiapamil)

PDB for HMDB0259069 (Tiapamil)

3D PDB for HMDB0259069 (Tiapamil)

SMILES for HMDB0259069 (Tiapamil)

INCHI for HMDB0259069 (Tiapamil)

Structure for HMDB0259069 (Tiapamil)

3D Structure for HMDB0259069 (Tiapamil)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized