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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:37:41 UTC

Update Date

2021-09-26 23:13:03 UTC

HMDB ID

HMDB0256987

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyrithioxin

Description

Pyritinol belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. Based on a literature review very few articles have been published on Pyritinol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pyrithioxin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pyrithioxin 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

HMDB0256987
     RDKit          3D
Pyrithioxin
 44 45  0  0  0  0  0  0  0  0999 V2000
    5.8119    0.1948    2.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451    0.3609    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7873    1.1741    1.9253 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    1.3706    0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162    0.6986   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280    0.6638   -1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    1.7137   -0.9234 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    1.0704   -2.3604 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057   -0.2578   -1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.0503   -1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -1.0486   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4273   -1.1220   -1.0691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569   -0.3088   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1205   -0.5858    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9515    0.7074    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    1.5994    1.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7032    0.7854   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    1.8544    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740    1.2940    1.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -0.1883   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068   -0.6499   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -2.0698   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -0.3817    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333   -1.1808    0.6296 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621    1.2439    3.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7687   -0.1904    2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -0.3991    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    2.0944    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    0.7994   -2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437   -0.4018   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717   -1.1205   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -0.7101   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269   -1.7817   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7981   -1.3750    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4957    0.2644    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8750   -1.0749   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3900    1.6219    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6852    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827    2.3122   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.8249    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6181   -0.4132   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -0.1753   -2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5882   -2.3954   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855   -1.7250   -0.2524 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 23  2  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
M  END

  Mrv1652306031606202D          

 24 25  0  0  0  0            999 V2000
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17  3  2  0  0  0  0
 17  9  1  0  0  0  0
 18  4  2  0  0  0  0
 18 10  1  0  0  0  0
 19  5  1  0  0  0  0
 20  6  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23  7  1  0  0  0  0
 24  8  1  0  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256987

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(O)C(CO)=C(CSSCC2=C(CO)C(O)=C(C)N=C2)C=N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O4S2/c1-9-15(21)13(5-19)11(3-17-9)7-23-24-8-12-4-18-10(2)16(22)14(12)6-20/h3-4,19-22H,5-8H2,1-2H3

> <INCHI_KEY>
SIXLXDIJGIWWFU-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O4S2

> <MOLECULAR_WEIGHT>
368.47

> <EXACT_MASS>
368.08644948

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.59570435299464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[({[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl}disulfanyl)methyl]-4-(hydroxymethyl)-2-methylpyridin-3-ol

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
0.4331187373333336

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.773360567399932

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.136698670508537

> <JCHEM_PKA_STRONGEST_BASIC>
6.0197069773136045

> <JCHEM_POLAR_SURFACE_AREA>
106.70000000000002

> <JCHEM_REFRACTIVITY>
98.77959999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyritinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256987
     RDKit          3D
Pyrithioxin
 44 45  0  0  0  0  0  0  0  0999 V2000
    5.8119    0.1948    2.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451    0.3609    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7873    1.1741    1.9253 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    1.3706    0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162    0.6986   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280    0.6638   -1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    1.7137   -0.9234 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    1.0704   -2.3604 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057   -0.2578   -1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.0503   -1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -1.0486   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4273   -1.1220   -1.0691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569   -0.3088   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1205   -0.5858    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9515    0.7074    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    1.5994    1.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7032    0.7854   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    1.8544    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740    1.2940    1.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -0.1883   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068   -0.6499   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -2.0698   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -0.3817    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333   -1.1808    0.6296 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621    1.2439    3.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7687   -0.1904    2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -0.3991    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    2.0944    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    0.7994   -2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437   -0.4018   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717   -1.1205   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -0.7101   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269   -1.7817   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7981   -1.3750    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4957    0.2644    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8750   -1.0749   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3900    1.6219    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6852    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827    2.3122   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.8249    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6181   -0.4132   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -0.1753   -2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5882   -2.3954   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855   -1.7250   -0.2524 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 23  2  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -4.001  -6.930   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.335  -1.540   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       0.000  -4.620   0.000  0.00  0.00           S+0
HETATM   24  S   UNK     0       1.334  -3.850   0.000  0.00  0.00           S+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11   17                                                       
CONECT    4   12   18                                                       
CONECT    5   13   19                                                       
CONECT    6   14   20                                                       
CONECT    7   11   23                                                       
CONECT    8   12   24                                                       
CONECT    9    1   15   17                                                  
CONECT   10    2   16   18                                                  
CONECT   11    3    7   13                                                  
CONECT   12    4    8   14                                                  
CONECT   13    5   11   15                                                  
CONECT   14    6   12   16                                                  
CONECT   15    9   13   21                                                  
CONECT   16   10   14   22                                                  
CONECT   17    3    9                                                       
CONECT   18    4   10                                                       
CONECT   19    5                                                            
CONECT   20    6                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    7   24                                                       
CONECT   24    8   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0256987
HETATM    1  C1  UNL     1       5.812   0.195   2.959  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.845   0.361   1.869  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.787   1.174   1.925  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.905   1.371   0.949  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.016   0.699  -0.233  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.028   0.664  -1.257  1.00  0.00           C  
HETATM    7  S1  UNL     1       0.549   1.714  -0.923  1.00  0.00           S  
HETATM    8  S2  UNL     1      -0.968   1.070  -2.360  1.00  0.00           S  
HETATM    9  C6  UNL     1      -1.906  -0.258  -1.661  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.264  -0.050  -1.216  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.207  -1.049  -1.621  1.00  0.00           C  
HETATM   12  N2  UNL     1      -5.427  -1.122  -1.069  1.00  0.00           N  
HETATM   13  C9  UNL     1      -5.857  -0.309  -0.131  1.00  0.00           C  
HETATM   14  C10 UNL     1      -7.120  -0.586   0.578  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.951   0.707   0.297  1.00  0.00           C  
HETATM   16  O1  UNL     1      -5.410   1.599   1.222  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.703   0.785  -0.249  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.713   1.854   0.240  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.274   1.294   1.422  1.00  0.00           O  
HETATM   20  C14 UNL     1       4.117  -0.188  -0.372  1.00  0.00           C  
HETATM   21  C15 UNL     1       4.407  -0.650  -1.750  1.00  0.00           C  
HETATM   22  O3  UNL     1       4.529  -2.070  -1.772  1.00  0.00           O  
HETATM   23  C16 UNL     1       5.038  -0.382   0.629  1.00  0.00           C  
HETATM   24  O4  UNL     1       6.133  -1.181   0.630  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.062   1.244   3.291  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.769  -0.190   2.553  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.430  -0.399   3.788  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.088   2.094   1.133  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.362   0.799  -2.310  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.544  -0.402  -1.182  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.872  -1.121  -2.427  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.246  -0.710  -0.836  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.927  -1.782  -2.350  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.798  -1.375   1.391  1.00  0.00           H  
HETATM   35  H11 UNL     1      -7.496   0.264   1.117  1.00  0.00           H  
HETATM   36  H12 UNL     1      -7.875  -1.075  -0.019  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.390   1.622   1.487  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.461   2.685   0.644  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.183   2.312  -0.474  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.874   1.825   2.113  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.618  -0.413  -1.818  1.00  0.00           H  
HETATM   42  H18 UNL     1       4.009  -0.175  -2.544  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.588  -2.395  -1.410  1.00  0.00           H  
HETATM   44  H20 UNL     1       6.286  -1.725  -0.252  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   23
CONECT    3    4
CONECT    4    5    5   28
CONECT    5    6   20
CONECT    6    7   29   30
CONECT    7    8
CONECT    8    9
CONECT    9   10   31   32
CONECT   10   11   11   17
CONECT   11   12   33
CONECT   12   13   13
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   16   17   17
CONECT   16   37
CONECT   17   18
CONECT   18   19   38   39
CONECT   19   40
CONECT   20   21   23   23
CONECT   21   22   41   42
CONECT   22   43
CONECT   23   24
CONECT   24   44
END

HMDB0256987
     RDKit          3D
Pyrithioxin
 44 45  0  0  0  0  0  0  0  0999 V2000
    5.8119    0.1948    2.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451    0.3609    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7873    1.1741    1.9253 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    1.3706    0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162    0.6986   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280    0.6638   -1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    1.7137   -0.9234 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    1.0704   -2.3604 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057   -0.2578   -1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.0503   -1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -1.0486   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4273   -1.1220   -1.0691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569   -0.3088   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1205   -0.5858    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9515    0.7074    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    1.5994    1.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7032    0.7854   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    1.8544    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740    1.2940    1.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -0.1883   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068   -0.6499   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -2.0698   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -0.3817    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333   -1.1808    0.6296 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621    1.2439    3.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7687   -0.1904    2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -0.3991    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    2.0944    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    0.7994   -2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437   -0.4018   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717   -1.1205   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -0.7101   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269   -1.7817   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7981   -1.3750    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4957    0.2644    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8750   -1.0749   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3900    1.6219    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6852    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827    2.3122   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.8249    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6181   -0.4132   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -0.1753   -2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5882   -2.3954   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855   -1.7250   -0.2524 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 23  2  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pyrithioxine	MeSH
Bonifen	MeSH
Enerbol	MeSH
Hydrochloride, pyritinol	MeSH
Piritinol	MeSH
Pyridoxinedisulfide	MeSH
Dipyridoxolyldisulfide	MeSH
Encephabol	MeSH
Piriditol	MeSH
Pyritinol hydrochloride	MeSH
Piritoxina	MeSH
Pyritinol	KEGG
5-[({[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl}disulphanyl)methyl]-4-(hydroxymethyl)-2-methylpyridin-3-ol	Generator

Chemical Formula

C₁₆H₂₀N₂O₄S₂

Average Molecular Weight

368.47

Monoisotopic Molecular Weight

368.08644948

IUPAC Name

5-[({[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl}disulfanyl)methyl]-4-(hydroxymethyl)-2-methylpyridin-3-ol

Traditional Name

pyritinol

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(CO)=C(CSSCC2=C(CO)C(O)=C(C)N=C2)C=N1

InChI Identifier

InChI=1S/C16H20N2O4S2/c1-9-15(21)13(5-19)11(3-17-9)7-23-24-8-12-4-18-10(2)16(22)14(12)6-20/h3-4,19-22H,5-8H2,1-2H3

InChI Key

SIXLXDIJGIWWFU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Methylpyridines

Direct Parent

Methylpyridines

Alternative Parents

Substituents

Hydroxypyridine
Methylpyridine
Heteroaromatic compound
Organic disulfide
Dialkyldisulfide
Azacycle
Sulfenyl compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic alcohol
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.57	ALOGPS
logP	0.43	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	6.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.78 m³·mol⁻¹	ChemAxon
Polarizability	38.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	185.276	30932474
DeepCCS	[M-H]-	182.726	30932474
DeepCCS	[M-2H]-	216.892	30932474
DeepCCS	[M+Na]+	193.086	30932474
AllCCS	[M+H]+	183.6	32859911
AllCCS	[M+H-H2O]+	180.9	32859911
AllCCS	[M+NH4]+	186.2	32859911
AllCCS	[M+Na]+	186.9	32859911
AllCCS	[M-H]-	180.7	32859911
AllCCS	[M+Na-2H]-	181.0	32859911
AllCCS	[M+HCOO]-	181.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyrithioxin	CC1=C(O)C(CO)=C(CSSCC2=C(CO)C(O)=C(C)N=C2)C=N1	3398.9	Standard polar	33892256
Pyrithioxin	CC1=C(O)C(CO)=C(CSSCC2=C(CO)C(O)=C(C)N=C2)C=N1	3286.5	Standard non polar	33892256
Pyrithioxin	CC1=C(O)C(CO)=C(CSSCC2=C(CO)C(O)=C(C)N=C2)C=N1	3495.5	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 - Pyrithioxin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0901000000-724a36d72aa73510e901	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrithioxin GC-MS (TBDMS_4_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrithioxin 10V, Positive-QTOF	splash10-0uxr-0509000000-b6c4a7c86915c5201622	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrithioxin 20V, Positive-QTOF	splash10-0uyi-0924000000-dec2f42c0b3d6efac80f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrithioxin 40V, Positive-QTOF	splash10-0uyr-1900000000-5999ce67f2cdad37fcb1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrithioxin 10V, Negative-QTOF	splash10-014i-0349000000-c346c83d862fac8516b3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrithioxin 20V, Negative-QTOF	splash10-00lr-0901000000-258e50f37af654a52d8a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrithioxin 40V, Negative-QTOF	splash10-0a4i-3913000000-996869b14e7ef65f251d	2017-07-26	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

DB13084

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyritinol

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 Pyrithioxin (HMDB0256987)

MOL for HMDB0256987 (Pyrithioxin)

3D MOL for HMDB0256987 (Pyrithioxin)

3D SDF for HMDB0256987 (Pyrithioxin)

3D-SDF for HMDB0256987 (Pyrithioxin)

PDB for HMDB0256987 (Pyrithioxin)

3D PDB for HMDB0256987 (Pyrithioxin)

SMILES for HMDB0256987 (Pyrithioxin)

INCHI for HMDB0256987 (Pyrithioxin)

Structure for HMDB0256987 (Pyrithioxin)

3D Structure for HMDB0256987 (Pyrithioxin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra