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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:44:02 UTC

Update Date

2021-09-26 22:59:57 UTC

HMDB ID

HMDB0249229

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Biotin sulfoxide

Description

5-{2-hydroxy-5-oxo-1H,3aH,4H,6H,6aH-5λ⁴-thieno[3,4-d]imidazol-6-yl}pentanoic acid belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring. Based on a literature review very few articles have been published on 5-{2-hydroxy-5-oxo-1H,3aH,4H,6H,6aH-5λ⁴-thieno[3,4-d]imidazol-6-yl}pentanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Biotin sulfoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Biotin sulfoxide 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

HMDB0249229
     RDKit          3D
Biotin sulfoxide
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.2341    0.3320    0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1638    0.2973   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    1.0416   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -0.5004   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    0.2156    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -0.5563    1.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -0.8659    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.3706   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    0.0685   -1.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -1.3898   -1.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7055   -1.8937   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -3.0777   -0.2687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3176   -0.7319    0.1142 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    0.4150   -0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920    1.6891    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744    1.4107    1.0757 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6308    2.7165    1.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.9740   -1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -0.7318   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -1.4606    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    0.3312    1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0262    1.2233    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -0.0816    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -1.5492    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.5288   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -1.3941    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341    1.0125   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001    0.4608   -2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.9975   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315   -0.6895    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6084    0.5640   -1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    1.8083    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    2.5177   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16  8  1  0
 14  9  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

  Mrv1533004241502332D          

 17 18  0  0  0  0            999 V2000
    0.8943   -4.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -3.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233   -4.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -4.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7522   -4.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -4.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1811   -4.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -4.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -3.8649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1543   -4.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7674   -3.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2405   -4.8569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4869   -5.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0744   -5.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674   -5.7354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6543   -6.2874    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249229

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCCC1C2NC(=O)NC2CS1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O4S/c13-8(14)4-2-1-3-7-9-6(5-17(7)16)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)

> <INCHI_KEY>
KCSKCIQYNAOBNQ-UHFFFAOYSA-N

> <FORMULA>
C10H16N2O4S

> <MOLECULAR_WEIGHT>
260.31

> <EXACT_MASS>
260.083078177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.62269016104382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{2,5-dioxo-hexahydro-1H-5λ⁴-thieno[3,4-d]imidazolidin-4-yl}pentanoic acid

> <ALOGPS_LOGP>
-0.87

> <JCHEM_LOGP>
-1.310258765

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.136335021523799

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9792459752182134

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8298725873605988

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
61.588199999999986

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
biotin sulfoxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249229
     RDKit          3D
Biotin sulfoxide
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.2341    0.3320    0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1638    0.2973   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    1.0416   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -0.5004   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    0.2156    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -0.5563    1.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -0.8659    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.3706   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    0.0685   -1.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -1.3898   -1.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7055   -1.8937   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -3.0777   -0.2687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3176   -0.7319    0.1142 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    0.4150   -0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920    1.6891    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744    1.4107    1.0757 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6308    2.7165    1.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.9740   -1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -0.7318   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -1.4606    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    0.3312    1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0262    1.2233    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -0.0816    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -1.5492    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.5288   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -1.3941    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341    1.0125   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001    0.4608   -2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.9975   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315   -0.6895    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6084    0.5640   -1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    1.8083    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    2.5177   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16  8  1  0
 14  9  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       1.669  -9.175   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.003  -8.405   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.003  -6.865   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.337  -9.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.670  -8.405   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.004  -9.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.338  -8.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.671  -9.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.078  -8.548   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      11.848  -7.214   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      13.355  -7.535   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.499  -6.504   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      13.516  -9.066   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      12.109  -9.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.339 -11.026   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       9.832 -10.706   0.000  0.00  0.00           S+0
HETATM   17  O   UNK     0       8.688 -11.737   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0249229
HETATM    1  O1  UNL     1       5.234   0.332   0.081  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.164   0.297  -0.583  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.136   1.042  -1.770  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.006  -0.500  -0.108  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.255   0.216   0.997  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.090  -0.556   1.495  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.052  -0.866   0.477  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.549   0.371  -0.140  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.582   0.069  -1.151  1.00  0.00           C  
HETATM   10  N1  UNL     1      -1.664  -1.390  -1.295  1.00  0.00           N  
HETATM   11  C8  UNL     1      -2.705  -1.894  -0.478  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.072  -3.078  -0.269  1.00  0.00           O  
HETATM   13  N2  UNL     1      -3.318  -0.732   0.114  1.00  0.00           N  
HETATM   14  C9  UNL     1      -2.931   0.415  -0.666  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.892   1.689   0.099  1.00  0.00           C  
HETATM   16  S1  UNL     1      -1.374   1.411   1.076  1.00  0.00           S  
HETATM   17  O4  UNL     1      -0.631   2.716   1.300  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.528   1.974  -1.840  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.366  -0.732  -0.972  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.404  -1.461   0.270  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.980   0.331   1.837  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.026   1.223   0.637  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.616  -0.082   2.356  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.489  -1.549   1.863  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.380  -1.529  -0.328  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.786  -1.394   1.000  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.234   1.013  -0.627  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.400   0.461  -2.161  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.069  -1.998  -1.893  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.932  -0.690   0.950  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.608   0.564  -1.544  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.762   1.808   0.753  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.687   2.518  -0.575  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8   25   26
CONECT    8    9   16   27
CONECT    9   10   14   28
CONECT   10   11   29
CONECT   11   12   12   13
CONECT   13   14   30
CONECT   14   15   31
CONECT   15   16   32   33
CONECT   16   17   17
END

HMDB0249229
     RDKit          3D
Biotin sulfoxide
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.2341    0.3320    0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1638    0.2973   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    1.0416   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -0.5004   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    0.2156    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -0.5563    1.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -0.8659    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.3706   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    0.0685   -1.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -1.3898   -1.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7055   -1.8937   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -3.0777   -0.2687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3176   -0.7319    0.1142 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    0.4150   -0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920    1.6891    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744    1.4107    1.0757 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6308    2.7165    1.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.9740   -1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -0.7318   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -1.4606    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    0.3312    1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0262    1.2233    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -0.0816    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -1.5492    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.5288   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -1.3941    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341    1.0125   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001    0.4608   -2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.9975   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315   -0.6895    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6084    0.5640   -1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    1.8083    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    2.5177   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16  8  1  0
 14  9  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-{2-hydroxy-5-oxo-1H,3ah,4H,6H,6ah-5-thieno[3,4-D]imidazol-6-yl}pentanoate	Generator
5-{2-hydroxy-5-oxo-1H,3ah,4H,6H,6ah-5λ⁴-thieno[3,4-D]imidazol-6-yl}pentanoate	Generator
Biotin sulfoxide	MeSH
D-Biotin-D-sulfoxide	MeSH
D-Biotin-D-sulphoxide	Generator

Chemical Formula

C₁₀H₁₆N₂O₄S

Average Molecular Weight

260.31

Monoisotopic Molecular Weight

260.083078177

IUPAC Name

5-{2,5-dioxo-hexahydro-1H-5λ⁴-thieno[3,4-d]imidazolidin-4-yl}pentanoic acid

Traditional Name

biotin sulfoxide

CAS Registry Number

Not Available

SMILES

OC(=O)CCCCC1C2NC(=O)NC2CS1=O

InChI Identifier

InChI=1S/C10H16N2O4S/c13-8(14)4-2-1-3-7-9-6(5-17(7)16)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)

InChI Key

KCSKCIQYNAOBNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Biotin and derivatives

Sub Class

Not Available

Direct Parent

Biotin and derivatives

Alternative Parents

Substituents

Biotin_derivative
Biotin
Thienoimidazolidine
Medium-chain fatty acid
Heterocyclic fatty acid
Imidazolidinone
Fatty acid
Fatty acyl
Imidazolidine
Thiolane
Thiophene
Carbonic acid derivative
Sulfoxide
Urea
Azacycle
Monocarboxylic acid or derivatives
Sulfinyl compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.87	ALOGPS
logP	-1.3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.59 m³·mol⁻¹	ChemAxon
Polarizability	25.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	148.853	30932474
DeepCCS	[M-H]-	146.495	30932474
DeepCCS	[M-2H]-	181.622	30932474
DeepCCS	[M+Na]+	156.845	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	158.9	32859911
AllCCS	[M+Na-2H]-	158.9	32859911
AllCCS	[M+HCOO]-	159.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Biotin sulfoxide	OC(=O)CCCCC1C2NC(=O)NC2CS1=O	4085.6	Standard polar	33892256
Biotin sulfoxide	OC(=O)CCCCC1C2NC(=O)NC2CS1=O	2263.8	Standard non polar	33892256
Biotin sulfoxide	OC(=O)CCCCC1C2NC(=O)NC2CS1=O	2693.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Biotin sulfoxide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)NC(=O)N2[Si](C)(C)C	2603.6	Semi standard non polar	33892256
Biotin sulfoxide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)NC(=O)N2[Si](C)(C)C	2565.9	Standard non polar	33892256
Biotin sulfoxide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)NC(=O)N2[Si](C)(C)C	3887.0	Standard polar	33892256
Biotin sulfoxide,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCC1C2NC(=O)N([Si](C)(C)C)C2CS1=O	2610.4	Semi standard non polar	33892256
Biotin sulfoxide,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCC1C2NC(=O)N([Si](C)(C)C)C2CS1=O	2553.5	Standard non polar	33892256
Biotin sulfoxide,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCC1C2NC(=O)N([Si](C)(C)C)C2CS1=O	3894.2	Standard polar	33892256
Biotin sulfoxide,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2C1CS(=O)C2CCCCC(=O)O	2517.3	Semi standard non polar	33892256
Biotin sulfoxide,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2C1CS(=O)C2CCCCC(=O)O	2572.6	Standard non polar	33892256
Biotin sulfoxide,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2C1CS(=O)C2CCCCC(=O)O	3255.6	Standard polar	33892256
Biotin sulfoxide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2462.2	Semi standard non polar	33892256
Biotin sulfoxide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2693.0	Standard non polar	33892256
Biotin sulfoxide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2985.7	Standard polar	33892256
Biotin sulfoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)NC(=O)N2[Si](C)(C)C(C)(C)C	3106.8	Semi standard non polar	33892256
Biotin sulfoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)NC(=O)N2[Si](C)(C)C(C)(C)C	3041.7	Standard non polar	33892256
Biotin sulfoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)NC(=O)N2[Si](C)(C)C(C)(C)C	3797.4	Standard polar	33892256
Biotin sulfoxide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2NC(=O)N([Si](C)(C)C(C)(C)C)C2CS1=O	3111.0	Semi standard non polar	33892256
Biotin sulfoxide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2NC(=O)N([Si](C)(C)C(C)(C)C)C2CS1=O	3033.2	Standard non polar	33892256
Biotin sulfoxide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2NC(=O)N([Si](C)(C)C(C)(C)C)C2CS1=O	3819.3	Standard polar	33892256
Biotin sulfoxide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2C1CS(=O)C2CCCCC(=O)O	3003.0	Semi standard non polar	33892256
Biotin sulfoxide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2C1CS(=O)C2CCCCC(=O)O	3057.2	Standard non polar	33892256
Biotin sulfoxide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2C1CS(=O)C2CCCCC(=O)O	3314.4	Standard polar	33892256
Biotin sulfoxide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	3195.3	Semi standard non polar	33892256
Biotin sulfoxide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	3384.0	Standard non polar	33892256
Biotin sulfoxide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC1C2C(CS1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	3183.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9750000000-fd0a280aae501c103f67	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin sulfoxide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	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 - Biotin sulfoxide 10V, Positive-QTOF	splash10-0006-0090000000-cc73686f7d58c464da9e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 20V, Positive-QTOF	splash10-0296-3290000000-8cea7a2402e427d742e6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 40V, Positive-QTOF	splash10-0089-9630000000-a604b7aa2a896435405a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 10V, Negative-QTOF	splash10-0a4j-2490000000-6f5aebb375f26f13888d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 20V, Negative-QTOF	splash10-0006-9260000000-e9dab3e8067446a75050	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 40V, Negative-QTOF	splash10-0006-9000000000-637032e42b9f9e64c4de	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 10V, Positive-QTOF	splash10-0006-0090000000-d758e70bbda1e3f9c7ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 20V, Positive-QTOF	splash10-0006-0090000000-2a8617b05a15d80d6b52	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 40V, Positive-QTOF	splash10-066s-5900000000-bf6205e22f26e35bed05	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 10V, Negative-QTOF	splash10-0a4i-0190000000-645519c85dbb47b3e4d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 20V, Negative-QTOF	splash10-0a4i-1190000000-0d95d95dc933d0956806	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin sulfoxide 40V, Negative-QTOF	splash10-0006-9530000000-c4074d85787bfc333da6	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

492321

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

566344

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 Biotin sulfoxide (HMDB0249229)

MOL for HMDB0249229 (Biotin sulfoxide)

3D MOL for HMDB0249229 (Biotin sulfoxide)

3D SDF for HMDB0249229 (Biotin sulfoxide)

3D-SDF for HMDB0249229 (Biotin sulfoxide)

PDB for HMDB0249229 (Biotin sulfoxide)

3D PDB for HMDB0249229 (Biotin sulfoxide)

SMILES for HMDB0249229 (Biotin sulfoxide)

INCHI for HMDB0249229 (Biotin sulfoxide)

Structure for HMDB0249229 (Biotin sulfoxide)

3D Structure for HMDB0249229 (Biotin sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra