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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:00:35 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259071

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tiaramide

Description

5-chloro-3-{2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl}-2,3-dihydro-1,3-benzothiazol-2-one belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom). Based on a literature review very few articles have been published on 5-chloro-3-{2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl}-2,3-dihydro-1,3-benzothiazol-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tiaramide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tiaramide 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

HMDB0259071
     RDKit          3D
TIARAMIDE
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.9041    0.9155    1.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    0.1886    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -0.9860   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8209   -0.6131   -0.4339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -0.3347   -1.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -0.3445   -2.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.0290   -1.6017 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0168   -0.1959    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1093   -0.0871    0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9594   -0.3361    2.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -0.6891    2.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -1.0090    4.4265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212   -0.7990    1.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.5474    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507    0.5391   -0.5366 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406   -0.2795   -1.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945    0.1156   -1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    0.1215   -0.7222 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887   -0.1826   -0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1357   -0.1548    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -0.4580    0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    1.3245    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    1.7009   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -1.7349    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -1.5551   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0361    0.1961    0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8111   -0.2443    2.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -1.0844    2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116   -0.1040   -2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.3560   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -0.5789   -2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304    1.1195   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -1.2472   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0144    0.4213   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    0.8605    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -0.9486    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9028   -0.3111    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.1060    1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    2.1758   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    2.4031   -1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954    2.1384    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 14  4  1  0
 23 15  1  0
 14  8  1  0
  3 24  1  0
  3 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END


  Mrv1652309112123002D          

 23 25  0  0  0  0            999 V2000
   -2.5223   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -5.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6731   -6.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -6.8577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 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
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259071

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H18ClN3O3S/c16-11-1-2-13-12(9-11)19(15(22)23-13)10-14(21)18-5-3-17(4-6-18)7-8-20/h1-2,9,20H,3-8,10H2

> <INCHI_KEY>
HTJXMOGUGMSZOG-UHFFFAOYSA-N

> <FORMULA>
C15H18ClN3O3S

> <MOLECULAR_WEIGHT>
355.84

> <EXACT_MASS>
355.0757403

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.12045985551394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-3-{2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl}-2,3-dihydro-1,3-benzothiazol-2-one

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.7330356010000003

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.748456219832057

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.071283240054196

> <JCHEM_PKA_STRONGEST_BASIC>
6.8435675153940165

> <JCHEM_POLAR_SURFACE_AREA>
64.09

> <JCHEM_REFRACTIVITY>
90.6708

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiaramide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259071
     RDKit          3D
TIARAMIDE
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.9041    0.9155    1.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    0.1886    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -0.9860   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8209   -0.6131   -0.4339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -0.3347   -1.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -0.3445   -2.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.0290   -1.6017 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0168   -0.1959    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1093   -0.0871    0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9594   -0.3361    2.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -0.6891    2.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -1.0090    4.4265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212   -0.7990    1.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.5474    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507    0.5391   -0.5366 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406   -0.2795   -1.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945    0.1156   -1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    0.1215   -0.7222 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887   -0.1826   -0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1357   -0.1548    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -0.4580    0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    1.3245    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    1.7009   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -1.7349    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -1.5551   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0361    0.1961    0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8111   -0.2443    2.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -1.0844    2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116   -0.1040   -2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.3560   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -0.5789   -2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304    1.1195   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -1.2472   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0144    0.4213   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    0.8605    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -0.9486    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9028   -0.3111    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.1060    1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    2.1758   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    2.4031   -1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954    2.1384    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 14  4  1  0
 23 15  1  0
 14  8  1  0
  3 24  1  0
  3 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  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      -4.708  -7.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.232  -6.118   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.726  -5.798   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.696  -6.943   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.171  -8.407   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -3.678  -8.727   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -4.154 -10.192   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.123 -11.336   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.599 -12.801   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.250  -4.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.281  -3.189   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       5.198  -2.843   0.000  0.00  0.00          Cl+0
HETATM   21  S   UNK     0      -0.268  -0.057   0.000  0.00  0.00           S+0
HETATM   22  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   15   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0259071
HETATM    1  O1  UNL     1      -0.904   0.915   1.178  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.590   0.189   0.202  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.404  -0.986  -0.135  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.821  -0.613  -0.434  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.152  -0.335  -1.697  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.387  -0.344  -2.724  1.00  0.00           O  
HETATM    7  S1  UNL     1      -4.815   0.029  -1.602  1.00  0.00           S  
HETATM    8  C4  UNL     1      -5.017  -0.196   0.083  1.00  0.00           C  
HETATM    9  C5  UNL     1      -6.109  -0.087   0.962  1.00  0.00           C  
HETATM   10  C6  UNL     1      -5.959  -0.336   2.309  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.694  -0.689   2.713  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -4.485  -1.009   4.426  1.00  0.00          CL  
HETATM   13  C8  UNL     1      -3.621  -0.799   1.868  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.755  -0.547   0.482  1.00  0.00           C  
HETATM   15  N2  UNL     1       0.551   0.539  -0.537  1.00  0.00           N  
HETATM   16  C10 UNL     1       0.941  -0.280  -1.664  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.394   0.116  -1.972  1.00  0.00           C  
HETATM   18  N3  UNL     1       3.100   0.122  -0.722  1.00  0.00           N  
HETATM   19  C12 UNL     1       4.489  -0.183  -0.846  1.00  0.00           C  
HETATM   20  C13 UNL     1       5.136  -0.155   0.506  1.00  0.00           C  
HETATM   21  O3  UNL     1       6.496  -0.458   0.353  1.00  0.00           O  
HETATM   22  C14 UNL     1       2.806   1.324   0.015  1.00  0.00           C  
HETATM   23  C15 UNL     1       1.354   1.701  -0.195  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.430  -1.735   0.712  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.984  -1.555  -0.984  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.036   0.196   0.507  1.00  0.00           H  
HETATM   27  H4  UNL     1      -6.811  -0.244   2.952  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.682  -1.084   2.315  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.312  -0.104  -2.570  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.988  -1.356  -1.402  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.820  -0.579  -2.719  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.330   1.119  -2.453  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.572  -1.247  -1.211  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.014   0.421  -1.607  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.013   0.860   0.941  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.662  -0.949   1.119  1.00  0.00           H  
HETATM   37  H14 UNL     1       6.903  -0.311   1.264  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.000   1.106   1.101  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.466   2.176  -0.246  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.315   2.403  -1.045  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.995   2.138   0.757  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4   24   25
CONECT    4    5   14
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   13
CONECT   13   14   14   28
CONECT   15   16   23
CONECT   16   17   29   30
CONECT   17   18   31   32
CONECT   18   19   22
CONECT   19   20   33   34
CONECT   20   21   35   36
CONECT   21   37
CONECT   22   23   38   39
CONECT   23   40   41
END

HMDB0259071
     RDKit          3D
TIARAMIDE
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.9041    0.9155    1.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    0.1886    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -0.9860   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8209   -0.6131   -0.4339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -0.3347   -1.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -0.3445   -2.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.0290   -1.6017 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0168   -0.1959    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1093   -0.0871    0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9594   -0.3361    2.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -0.6891    2.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -1.0090    4.4265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212   -0.7990    1.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.5474    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507    0.5391   -0.5366 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406   -0.2795   -1.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945    0.1156   -1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    0.1215   -0.7222 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887   -0.1826   -0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1357   -0.1548    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -0.4580    0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    1.3245    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    1.7009   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -1.7349    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -1.5551   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0361    0.1961    0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8111   -0.2443    2.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -1.0844    2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116   -0.1040   -2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.3560   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -0.5789   -2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304    1.1195   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -1.2472   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0144    0.4213   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    0.8605    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -0.9486    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9028   -0.3111    1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.1060    1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    2.1758   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    2.4031   -1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954    2.1384    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 14  4  1  0
 23 15  1  0
 14  8  1  0
  3 24  1  0
  3 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
NTA-194	MeSH
Solantal	MeSH
Tiaramide monohydrochloride	MeSH

Chemical Formula

C₁₅H₁₈ClN₃O₃S

Average Molecular Weight

355.84

Monoisotopic Molecular Weight

355.0757403

IUPAC Name

5-chloro-3-{2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl}-2,3-dihydro-1,3-benzothiazol-2-one

Traditional Name

tiaramide

CAS Registry Number

Not Available

SMILES

OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C15H18ClN3O3S/c16-11-1-2-13-12(9-11)19(15(22)23-13)10-14(21)18-5-3-17(4-6-18)7-8-20/h1-2,9,20H,3-8,10H2

InChI Key

HTJXMOGUGMSZOG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazoles

Sub Class

Not Available

Direct Parent

Benzothiazoles

Alternative Parents

Substituents

1,3-benzothiazole
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Benzenoid
Azole
Tertiary carboxylic acid amide
Thiazole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
1,2-aminoalcohol
Carboxamide group
Azacycle
Alkanolamine
Carboxylic acid derivative
Alcohol
Organic oxide
Organohalogen compound
Organochloride
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.7	ALOGPS
logP	0.73	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.07	ChemAxon
pKa (Strongest Basic)	6.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.67 m³·mol⁻¹	ChemAxon
Polarizability	36.12 Å³	ChemAxon
Number of Rings	3	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]+	175.136	30932474
DeepCCS	[M-H]-	172.778	30932474
DeepCCS	[M-2H]-	205.729	30932474
DeepCCS	[M+Na]+	181.229	30932474
AllCCS	[M+H]+	175.6	32859911
AllCCS	[M+H-H2O]+	172.9	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	176.5	32859911
AllCCS	[M+Na-2H]-	176.4	32859911
AllCCS	[M+HCOO]-	176.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
TIARAMIDE	OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=C1C=C(Cl)C=C2	4195.6	Standard polar	33892256
TIARAMIDE	OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=C1C=C(Cl)C=C2	2892.6	Standard non polar	33892256
TIARAMIDE	OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=C1C=C(Cl)C=C2	3187.2	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 - Tiaramide GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-6913000000-1348a32bb946857ee943	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiaramide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiaramide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiaramide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

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

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 Tiaramide (HMDB0259071)

MOL for HMDB0259071 (Tiaramide)

3D MOL for HMDB0259071 (Tiaramide)

3D SDF for HMDB0259071 (Tiaramide)

3D-SDF for HMDB0259071 (Tiaramide)

PDB for HMDB0259071 (Tiaramide)

3D PDB for HMDB0259071 (Tiaramide)

SMILES for HMDB0259071 (Tiaramide)

INCHI for HMDB0259071 (Tiaramide)

Structure for HMDB0259071 (Tiaramide)

3D Structure for HMDB0259071 (Tiaramide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra