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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:24:46 UTC

Update Date

2021-09-26 23:17:20 UTC

HMDB ID

HMDB0259653

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide

Description

Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide, also known as 3-hydroxymethyldibenzo(b,F)thiepin 5,5-dioxide, belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring. Based on a literature review very few articles have been published on Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide 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

HMDB0259653
     RDKit          3D
Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.3352   -0.5868    2.6518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797    0.3740    1.5183 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.0385    1.7222    2.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    0.4535    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    1.5720    1.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.8301    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    0.9426   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7628   -0.1670   -0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4859   -0.4258   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -1.6416   -0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6294   -1.9493   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -1.1570   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -1.4834   -1.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.8368   -1.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.1315   -0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    0.8267   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0864    0.0648    0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794    0.4590    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607   -0.1967    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529    2.2767    1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916    2.7135    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4597    1.1429   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -0.8782   -1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -2.3773   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9098   -1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4707   -2.2292   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -1.0372   -2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    1.8261    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7843    0.9590   -1.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099   -0.6151   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    1.1968    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19  2  1  0
  9  4  1  0
 19 12  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv1652309122100252D          

 19 21  0  0  0  0            999 V2000
    6.1237    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.6953    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291    2.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1782    2.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2741    1.9733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 10 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
  9 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259653

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CC2=C(C=C1)C=CC1=CC=CC=C1S2(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O3S/c16-10-11-5-6-13-8-7-12-3-1-2-4-14(12)19(17,18)15(13)9-11/h1-9,16H,10H2

> <INCHI_KEY>
NYFDVYBQHBRTNS-UHFFFAOYSA-N

> <FORMULA>
C15H12O3S

> <MOLECULAR_WEIGHT>
272.32

> <EXACT_MASS>
272.05071542

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.874327253075442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-(hydroxymethyl)-2lambda6-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene-2,2-dione

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.5273259119999993

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.719668258929346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9214171035443037

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
75.80290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(hydroxymethyl)-2lambda6-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene-2,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259653
     RDKit          3D
Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.3352   -0.5868    2.6518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797    0.3740    1.5183 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.0385    1.7222    2.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    0.4535    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    1.5720    1.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.8301    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    0.9426   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7628   -0.1670   -0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4859   -0.4258   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -1.6416   -0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6294   -1.9493   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -1.1570   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -1.4834   -1.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.8368   -1.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.1315   -0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    0.8267   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0864    0.0648    0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794    0.4590    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607   -0.1967    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529    2.2767    1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916    2.7135    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4597    1.1429   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -0.8782   -1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -2.3773   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9098   -1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4707   -2.2292   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -1.0372   -2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    1.8261    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7843    0.9590   -1.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099   -0.6151   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    1.1968    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19  2  1  0
  9  4  1  0
 19 12  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0      11.431   1.588   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.088   3.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.617   3.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.488   2.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.830   0.995   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.302   0.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.870  -0.209   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.330  -0.209   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.370   0.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.713   2.496   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       7.100   3.165   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       6.401   4.537   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.799   4.537   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.584   3.544   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.112   3.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.770   1.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.898   0.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.983   4.137   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.512   3.683   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10    4   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    9                                                       
CONECT   18   15   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0259653
HETATM    1  O1  UNL     1      -0.335  -0.587   2.652  1.00  0.00           O  
HETATM    2  S1  UNL     1      -0.380   0.374   1.518  1.00  0.00           S  
HETATM    3  O2  UNL     1       0.038   1.722   2.032  1.00  0.00           O  
HETATM    4  C1  UNL     1      -1.953   0.454   0.761  1.00  0.00           C  
HETATM    5  C2  UNL     1      -2.661   1.572   1.196  1.00  0.00           C  
HETATM    6  C3  UNL     1      -3.928   1.830   0.730  1.00  0.00           C  
HETATM    7  C4  UNL     1      -4.462   0.943  -0.179  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.763  -0.167  -0.612  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.486  -0.426  -0.141  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.898  -1.642  -0.711  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.629  -1.949  -0.938  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.592  -1.157  -0.684  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.609  -1.483  -1.568  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.819  -0.837  -1.474  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.985   0.131  -0.486  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.299   0.827  -0.391  1.00  0.00           C  
HETATM   17  O3  UNL     1       5.086   0.065   0.488  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.979   0.459   0.394  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.761  -0.197   0.294  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.253   2.277   1.910  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.492   2.713   1.071  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.460   1.143  -0.548  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.175  -0.878  -1.332  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.630  -2.377  -0.980  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.389  -2.910  -1.374  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.471  -2.229  -2.322  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.660  -1.037  -2.128  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.106   1.826   0.046  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.784   0.959  -1.370  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.610  -0.615  -0.039  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.093   1.197   1.153  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4   19
CONECT    4    5    5    9
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   19
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16   18
CONECT   16   17   28   29
CONECT   17   30
CONECT   18   19   19   31
END

HMDB0259653
     RDKit          3D
Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.3352   -0.5868    2.6518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797    0.3740    1.5183 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.0385    1.7222    2.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    0.4535    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    1.5720    1.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.8301    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    0.9426   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7628   -0.1670   -0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4859   -0.4258   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -1.6416   -0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6294   -1.9493   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -1.1570   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -1.4834   -1.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.8368   -1.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.1315   -0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    0.8267   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0864    0.0648    0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794    0.4590    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607   -0.1967    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529    2.2767    1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916    2.7135    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4597    1.1429   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -0.8782   -1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -2.3773   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9098   -1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4707   -2.2292   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -1.0372   -2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    1.8261    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7843    0.9590   -1.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099   -0.6151   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    1.1968    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19  2  1  0
  9  4  1  0
 19 12  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxymethyldibenzo(b,F)thiepin 5,5-dioxide	HMDB

Chemical Formula

C₁₅H₁₂O₃S

Average Molecular Weight

272.32

Monoisotopic Molecular Weight

272.05071542

IUPAC Name

14-(hydroxymethyl)-2lambda6-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene-2,2-dione

Traditional Name

14-(hydroxymethyl)-2lambda6-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene-2,2-dione

CAS Registry Number

Not Available

SMILES

OCC1=CC2=C(C=C1)C=CC1=CC=CC=C1S2(=O)=O

InChI Identifier

InChI=1S/C15H12O3S/c16-10-11-5-6-13-8-7-12-3-1-2-4-14(12)19(17,18)15(13)9-11/h1-9,16H,10H2

InChI Key

NYFDVYBQHBRTNS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiepins

Sub Class

Dibenzothiepins

Direct Parent

Dibenzothiepins

Alternative Parents

Substituents

Dibenzothiepin
Benzenoid
Sulfone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
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	2.03	ALOGPS
logP	2.53	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.72	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.8 m³·mol⁻¹	ChemAxon
Polarizability	27.87 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]+	155.55	30932474
DeepCCS	[M-H]-	153.192	30932474
DeepCCS	[M-2H]-	186.078	30932474
DeepCCS	[M+Na]+	161.643	30932474
AllCCS	[M+H]+	162.4	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	167.0	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1912.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	360.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	126.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	518.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	518.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1089.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	409.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1355.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	357.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	252.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	81.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide	OCC1=CC2=C(C=C1)C=CC1=CC=CC=C1S2(=O)=O	3679.4	Standard polar	33892256
Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide	OCC1=CC2=C(C=C1)C=CC1=CC=CC=C1S2(=O)=O	2662.9	Standard non polar	33892256
Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide	OCC1=CC2=C(C=C1)C=CC1=CC=CC=C1S2(=O)=O	2738.5	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 - Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0390000000-d0f8e969e7d37da61c4c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide 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

113151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127538

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 Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide (HMDB0259653)

MOL for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

3D MOL for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

3D SDF for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

3D-SDF for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

PDB for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

3D PDB for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

SMILES for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

INCHI for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

Structure for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

3D Structure for HMDB0259653 (Dibenzo(b,f)thiepin-3-methanol, 5,5-dioxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra