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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:03:33 UTC

Update Date

2021-09-26 23:12:17 UTC

HMDB ID

HMDB0256544

Secondary Accession Numbers

None

Metabolite Identification

Common Name

pifithrin

Description

pifithrin, also known as PFT alpha, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review a significant number of articles have been published on pifithrin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pifithrin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically pifithrin 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

HMDB0256544
     RDKit          3D
pifithrin
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.2100    1.0903    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8030    0.6563    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0648    0.4560    1.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.0482    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252   -0.1711   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478   -0.5977   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -0.7843   -1.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412   -0.8115    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.2447    0.7042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377   -0.4285    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6394   -0.9769    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849   -2.6415    0.1650 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -2.5504    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7941   -3.5535    0.7248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9107   -0.2689   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.1940    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    1.6028   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050    1.0881    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.0272   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1811    0.4363   -1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737    1.9975   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.2858    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744    0.2996   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    0.6108    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692   -0.1073    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917    0.1605    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147   -1.5259    1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -4.5249    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7707   -0.6857    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1811   -0.3394   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.7902   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7466    1.2859    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    1.1173   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061    2.6940   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5730    1.4319    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246    1.4774    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -0.1260   -2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435    0.5880   -2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 13  9  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

  Mrv1652309112119032D          

 20 22  0  0  0  0            999 V2000
   -2.2252   -5.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 C   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
   -1.2054   -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
   -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 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256544

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)C(=O)CN1C(=N)SC2=C1CCCC2

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2OS/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17/h6-9,17H,2-5,10H2,1H3

> <INCHI_KEY>
OLTZHXYLLRJLST-UHFFFAOYSA-N

> <FORMULA>
C16H18N2OS

> <MOLECULAR_WEIGHT>
286.39

> <EXACT_MASS>
286.113984382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.934667011355685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-imino-2,3,4,5,6,7-hexahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethan-1-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.5595600039999997

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.134456061510559

> <JCHEM_PKA_STRONGEST_BASIC>
2.643402334784126

> <JCHEM_POLAR_SURFACE_AREA>
44.160000000000004

> <JCHEM_REFRACTIVITY>
96.4317

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256544
     RDKit          3D
pifithrin
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.2100    1.0903    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8030    0.6563    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0648    0.4560    1.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.0482    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252   -0.1711   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478   -0.5977   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -0.7843   -1.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412   -0.8115    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.2447    0.7042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377   -0.4285    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6394   -0.9769    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849   -2.6415    0.1650 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -2.5504    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7941   -3.5535    0.7248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9107   -0.2689   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.1940    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    1.6028   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050    1.0881    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.0272   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1811    0.4363   -1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737    1.9975   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.2858    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744    0.2996   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    0.6108    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692   -0.1073    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917    0.1605    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147   -1.5259    1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -4.5249    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7707   -0.6857    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1811   -0.3394   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.7902   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7466    1.2859    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    1.1173   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061    2.6940   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5730    1.4319    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246    1.4774    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -0.1260   -2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435    0.5880   -2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 13  9  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  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      -4.154 -10.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.678  -8.727   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.708  -7.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.232  -6.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.726  -5.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.696  -6.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.171  -8.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.250  -4.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.281  -3.189   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0      -0.268  -0.057   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.713  -1.303   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   13   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0256544
HETATM    1  C1  UNL     1       6.210   1.090   0.135  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.803   0.656   0.090  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.065   0.456   1.232  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.744   0.048   1.176  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.125  -0.171  -0.046  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.748  -0.598  -0.160  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.227  -0.784  -1.271  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.041  -0.812   1.068  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.421  -1.245   0.704  1.00  0.00           N  
HETATM   10  C8  UNL     1      -2.438  -0.429   0.501  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.639  -0.977   0.174  1.00  0.00           C  
HETATM   12  S1  UNL     1      -3.285  -2.642   0.165  1.00  0.00           S  
HETATM   13  C10 UNL     1      -1.633  -2.550   0.577  1.00  0.00           C  
HETATM   14  N2  UNL     1      -0.794  -3.554   0.725  1.00  0.00           N  
HETATM   15  C11 UNL     1      -4.911  -0.269  -0.098  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.793   1.194   0.228  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.439   1.603  -0.371  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.405   1.088   0.596  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.857   0.027  -1.186  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.181   0.436  -1.117  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.374   1.998  -0.507  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.545   1.286   1.162  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.874   0.300  -0.273  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.493   0.611   2.211  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.169  -0.107   2.081  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.092   0.160   1.596  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.415  -1.526   1.774  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.081  -4.525   0.598  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.771  -0.686   0.454  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.181  -0.339  -1.189  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.608   1.790  -0.176  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.747   1.286   1.351  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.326   1.117  -1.343  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.406   2.694  -0.400  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.573   1.432   1.615  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.425   1.477   0.257  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.435  -0.126  -2.174  1.00  0.00           H  
HETATM   38  H18 UNL     1       4.743   0.588  -2.023  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   20
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    8    9   26   27
CONECT    9   10   13
CONECT   10   11   11   18
CONECT   11   12   15
CONECT   12   13
CONECT   13   14   14
CONECT   14   28
CONECT   15   16   29   30
CONECT   16   17   31   32
CONECT   17   18   33   34
CONECT   18   35   36
CONECT   19   20   20   37
CONECT   20   38
END

HMDB0256544
     RDKit          3D
pifithrin
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.2100    1.0903    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8030    0.6563    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0648    0.4560    1.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.0482    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252   -0.1711   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478   -0.5977   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -0.7843   -1.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412   -0.8115    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.2447    0.7042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377   -0.4285    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6394   -0.9769    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849   -2.6415    0.1650 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -2.5504    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7941   -3.5535    0.7248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9107   -0.2689   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.1940    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    1.6028   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050    1.0881    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.0272   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1811    0.4363   -1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737    1.9975   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.2858    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744    0.2996   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    0.6108    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692   -0.1073    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917    0.1605    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147   -1.5259    1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -4.5249    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7707   -0.6857    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1811   -0.3394   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.7902   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7466    1.2859    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    1.1173   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061    2.6940   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5730    1.4319    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246    1.4774    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -0.1260   -2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435    0.5880   -2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 13  9  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)- benzothiazolyl)ethanone hydrobromide	HMDB
1-(4-Methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)ethanone hydrobromide (1:1)	HMDB
2-(2-Imino-4,5,6,7-tetrahydrobenzothiazol-3-yl)-1-p-tolylethanone	HMDB
PFT alpha	HMDB
Ethanone, 1-(4-methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)-, hydrobromide (1:1)	HMDB
Pifithrin-alpha	HMDB

Chemical Formula

C₁₆H₁₈N₂OS

Average Molecular Weight

286.39

Monoisotopic Molecular Weight

286.113984382

IUPAC Name

2-(2-imino-2,3,4,5,6,7-hexahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethan-1-one

Traditional Name

2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethanone

CAS Registry Number

Not Available

SMILES

CC1=CC=C(C=C1)C(=O)CN1C(=N)SC2=C1CCCC2

InChI Identifier

InChI=1S/C16H18N2OS/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17/h6-9,17H,2-5,10H2,1H3

InChI Key

OLTZHXYLLRJLST-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Toluene
Monocyclic benzene moiety
Benzenoid
Azole
Thiazole
Heteroaromatic compound
Isothiourea
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
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)

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	3.01	ALOGPS
logP	3.56	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	2.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.16 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.43 m³·mol⁻¹	ChemAxon
Polarizability	31.93 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]+	165.845	30932474
DeepCCS	[M-H]-	163.487	30932474
DeepCCS	[M-2H]-	196.636	30932474
DeepCCS	[M+Na]+	171.938	30932474
AllCCS	[M+H]+	166.3	32859911
AllCCS	[M+H-H2O]+	162.8	32859911
AllCCS	[M+NH4]+	169.4	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	170.7	32859911
AllCCS	[M+HCOO]-	170.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
pifithrin	CC1=CC=C(C=C1)C(=O)CN1C(=N)SC2=C1CCCC2	4296.6	Standard polar	33892256
pifithrin	CC1=CC=C(C=C1)C(=O)CN1C(=N)SC2=C1CCCC2	2648.3	Standard non polar	33892256
pifithrin	CC1=CC=C(C=C1)C(=O)CN1C(=N)SC2=C1CCCC2	2727.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
pifithrin,1TMS,isomer #1	CC1=CC=C(C(=O)CN2C3=C(CCCC3)SC2=N[Si](C)(C)C)C=C1	2666.8	Semi standard non polar	33892256
pifithrin,1TMS,isomer #1	CC1=CC=C(C(=O)CN2C3=C(CCCC3)SC2=N[Si](C)(C)C)C=C1	2476.4	Standard non polar	33892256
pifithrin,1TMS,isomer #1	CC1=CC=C(C(=O)CN2C3=C(CCCC3)SC2=N[Si](C)(C)C)C=C1	3371.8	Standard polar	33892256
pifithrin,1TBDMS,isomer #1	CC1=CC=C(C(=O)CN2C3=C(CCCC3)SC2=N[Si](C)(C)C(C)(C)C)C=C1	2895.7	Semi standard non polar	33892256
pifithrin,1TBDMS,isomer #1	CC1=CC=C(C(=O)CN2C3=C(CCCC3)SC2=N[Si](C)(C)C(C)(C)C)C=C1	2699.1	Standard non polar	33892256
pifithrin,1TBDMS,isomer #1	CC1=CC=C(C(=O)CN2C3=C(CCCC3)SC2=N[Si](C)(C)C(C)(C)C)C=C1	3455.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - pifithrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-7910000000-747fcde1ea6df573bc5a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - pifithrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

13248388

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pifithrin

METLIN ID

Not Available

PubChem Compound

4817

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 pifithrin (HMDB0256544)

MOL for HMDB0256544 (pifithrin)

3D MOL for HMDB0256544 (pifithrin)

3D SDF for HMDB0256544 (pifithrin)

3D-SDF for HMDB0256544 (pifithrin)

PDB for HMDB0256544 (pifithrin)

3D PDB for HMDB0256544 (pifithrin)

SMILES for HMDB0256544 (pifithrin)

INCHI for HMDB0256544 (pifithrin)

Structure for HMDB0256544 (pifithrin)

3D Structure for HMDB0256544 (pifithrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra