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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:41:30 UTC

Update Date

2021-09-26 23:08:23 UTC

HMDB ID

HMDB0254410

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mefruside

Description

Mefruside, also known as baycaron, belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. Based on a literature review very few articles have been published on Mefruside. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mefruside is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mefruside 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

HMDB0254410
     RDKit          3D
Mefruside
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.5202   -0.8176    1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -0.3745    0.5009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169    0.2737    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -0.5627   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -1.5963    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588    0.3250   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6945   -0.0404   -1.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -0.4573   -2.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -1.1859   -1.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -0.5412   -0.6936 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.7350   -2.0089   -0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1378   -0.1371   -2.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142    0.3396   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    1.6345   -0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    2.4058   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923    1.8546    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714    2.7763    0.3222 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0179    0.5669    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3693   -0.1097    1.3520 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.8009   -0.1538    0.4204 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313   -1.4898    1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140    0.7522    2.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.1851    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -1.8628    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.1966    2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.7155    2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800    1.1059   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817    0.7897    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193   -2.0814    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -1.1096    1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -2.3956    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    0.1284    0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    1.3906   -0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0741    0.8424   -2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.8743   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -1.1154   -3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690    0.4471   -2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882    2.1146   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038    3.4304   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7369   -0.6810   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3271    0.7256    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -1.2108    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 19 22  2  0
 18 23  2  0
  9  4  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 14 38  1  0
 15 39  1  0
 20 40  1  0
 20 41  1  0
 23 42  1  0
M  END


  Mrv1572004221606212D          

 23 24  0  0  0  0            999 V2000
   -3.3819    4.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    3.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4174    2.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402    4.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9922    5.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1624    2.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424    2.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217    5.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778    4.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668    5.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7373    6.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697    6.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299    3.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893    6.9504    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    8.0781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709    3.8849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    7.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    7.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    3.9460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319    5.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    2.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    7.2935    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188    4.4980    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  1  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  1  0  0  0  0
 21  7  1  0  0  0  0
 21 13  1  0  0  0  0
 22 12  1  0  0  0  0
 22 15  1  0  0  0  0
 22 17  2  0  0  0  0
 22 18  2  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  2  0  0  0  0
 23 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254410

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CC1(C)CCCO1)S(=O)(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H19ClN2O5S2/c1-13(6-3-7-21-13)9-16(2)23(19,20)10-4-5-11(14)12(8-10)22(15,17)18/h4-5,8H,3,6-7,9H2,1-2H3,(H2,15,17,18)

> <INCHI_KEY>
SMNOERSLNYGGOU-UHFFFAOYSA-N

> <FORMULA>
C13H19ClN2O5S2

> <MOLECULAR_WEIGHT>
382.87

> <EXACT_MASS>
382.0423918

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.05941715393175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-chloro-N1-methyl-N1-[(2-methyloxolan-2-yl)methyl]benzene-1,3-disulfonamide

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.935869859666667

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.683652990107166

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1736185900343346

> <JCHEM_POLAR_SURFACE_AREA>
106.77

> <JCHEM_REFRACTIVITY>
87.86489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mefruside

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254410
     RDKit          3D
Mefruside
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.5202   -0.8176    1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -0.3745    0.5009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169    0.2737    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -0.5627   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -1.5963    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588    0.3250   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6945   -0.0404   -1.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -0.4573   -2.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -1.1859   -1.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -0.5412   -0.6936 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.7350   -2.0089   -0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1378   -0.1371   -2.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142    0.3396   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    1.6345   -0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    2.4058   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923    1.8546    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714    2.7763    0.3222 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0179    0.5669    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3693   -0.1097    1.3520 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.8009   -0.1538    0.4204 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313   -1.4898    1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140    0.7522    2.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.1851    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -1.8628    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.1966    2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.7155    2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800    1.1059   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817    0.7897    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193   -2.0814    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -1.1096    1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -2.3956    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    0.1284    0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    1.3906   -0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0741    0.8424   -2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.8743   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -1.1154   -3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690    0.4471   -2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882    2.1146   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038    3.4304   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7369   -0.6810   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3271    0.7256    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -1.2108    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 19 22  2  0
 18 23  2  0
  9  4  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 14 38  1  0
 15 39  1  0
 20 40  1  0
 20 41  1  0
 23 42  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -6.313   7.572   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.270   5.787   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.512   4.058   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.822   9.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.852  10.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.037   5.522   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.052   4.058   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.161  11.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.252   7.572   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.685   9.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.376  11.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.130  12.150   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.282   6.428   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       2.407  12.974   0.000  0.00  0.00          Cl+0
HETATM   15  N   UNK     0      -1.082  15.079   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -2.746   7.252   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       0.859  14.090   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.071  13.139   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.571   7.366   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.860   9.427   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.528   5.522   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0      -0.606  13.614   0.000  0.00  0.00           S+0
HETATM   23  S   UNK     0      -1.715   8.396   0.000  0.00  0.00           S+0
CONECT    1   13                                                            
CONECT    2   16                                                            
CONECT    3    6    7                                                       
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    3   13                                                       
CONECT    7    3   21                                                       
CONECT    8   10   12                                                       
CONECT    9   13   16                                                       
CONECT   10    4    8   23                                                  
CONECT   11    5   12   14                                                  
CONECT   12    8   11   22                                                  
CONECT   13    1    6    9   21                                             
CONECT   14   11                                                            
CONECT   15   22                                                            
CONECT   16    2    9   23                                                  
CONECT   17   22                                                            
CONECT   18   22                                                            
CONECT   19   23                                                            
CONECT   20   23                                                            
CONECT   21    7   13                                                       
CONECT   22   12   15   17   18                                             
CONECT   23   10   16   19   20                                             
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0254410
HETATM    1  C1  UNL     1      -0.520  -0.818   1.792  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.820  -0.374   0.501  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.017   0.274   0.235  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.157  -0.563  -0.257  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.607  -1.596   0.746  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.359   0.325  -0.540  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.694  -0.040  -1.972  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.340  -0.457  -2.495  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.822  -1.186  -1.445  1.00  0.00           O  
HETATM   10  S1  UNL     1       0.333  -0.541  -0.694  1.00  0.00           S  
HETATM   11  O2  UNL     1       0.735  -2.009  -0.788  1.00  0.00           O  
HETATM   12  O3  UNL     1      -0.138  -0.137  -2.061  1.00  0.00           O  
HETATM   13  C8  UNL     1       1.814   0.340  -0.384  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.892   1.634  -0.852  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.028   2.406  -0.652  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.092   1.855   0.029  1.00  0.00           C  
HETATM   17 CL1  UNL     1       5.571   2.776   0.322  1.00  0.00          CL  
HETATM   18  C12 UNL     1       4.018   0.567   0.496  1.00  0.00           C  
HETATM   19  S2  UNL     1       5.369  -0.110   1.352  1.00  0.00           S  
HETATM   20  N2  UNL     1       6.801  -0.154   0.420  1.00  0.00           N  
HETATM   21  O4  UNL     1       5.031  -1.490   1.832  1.00  0.00           O  
HETATM   22  O5  UNL     1       5.614   0.752   2.561  1.00  0.00           O  
HETATM   23  C13 UNL     1       2.885  -0.185   0.290  1.00  0.00           C  
HETATM   24  H1  UNL     1      -0.104  -1.863   1.782  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.311  -0.197   2.234  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.371  -0.715   2.463  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.880   1.106  -0.498  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.382   0.790   1.171  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.519  -2.081   0.294  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.911  -1.110   1.672  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.881  -2.396   0.908  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.200   0.128   0.136  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.087   1.391  -0.474  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.074   0.842  -2.517  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.425  -0.874  -1.952  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.502  -1.115  -3.371  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.769   0.447  -2.751  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.088   2.115  -1.391  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.104   3.430  -1.016  1.00  0.00           H  
HETATM   40  H17 UNL     1       6.737  -0.681  -0.455  1.00  0.00           H  
HETATM   41  H18 UNL     1       7.327   0.726   0.392  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.826  -1.211   0.661  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   10
CONECT    3    4   27   28
CONECT    4    5    6    9
CONECT    5   29   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   14   14   23
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   17   18
CONECT   18   19   23   23
CONECT   19   20   21   21   22
CONECT   19   22
CONECT   20   40   41
CONECT   23   42
END

HMDB0254410
     RDKit          3D
Mefruside
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.5202   -0.8176    1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -0.3745    0.5009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169    0.2737    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -0.5627   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -1.5963    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588    0.3250   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6945   -0.0404   -1.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -0.4573   -2.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -1.1859   -1.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -0.5412   -0.6936 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.7350   -2.0089   -0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1378   -0.1371   -2.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142    0.3396   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    1.6345   -0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    2.4058   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923    1.8546    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714    2.7763    0.3222 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0179    0.5669    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3693   -0.1097    1.3520 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.8009   -0.1538    0.4204 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313   -1.4898    1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140    0.7522    2.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.1851    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -1.8628    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.1966    2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.7155    2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800    1.1059   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817    0.7897    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193   -2.0814    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -1.1096    1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -2.3956    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    0.1284    0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    1.3906   -0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0741    0.8424   -2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.8743   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -1.1154   -3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690    0.4471   -2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882    2.1146   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038    3.4304   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7369   -0.6810   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3271    0.7256    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -1.2108    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 19 22  2  0
 18 23  2  0
  9  4  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 14 38  1  0
 15 39  1  0
 20 40  1  0
 20 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Baycaron	Kegg
4-chloro-1-N-Methyl-1-N-[(2-methyloxolan-2-yl)methyl]benzene-1,3-disulphonamide	Generator
Mefruside	MeSH
4-Chloro-N1-methyl-N1-[(2-methyloxolan-2-yl)methyl]benzene-1,3-disulphonamide	Generator

Chemical Formula

C₁₃H₁₉ClN₂O₅S₂

Average Molecular Weight

382.87

Monoisotopic Molecular Weight

382.0423918

IUPAC Name

4-chloro-N1-methyl-N1-[(2-methyloxolan-2-yl)methyl]benzene-1,3-disulfonamide

Traditional Name

mefruside

CAS Registry Number

Not Available

SMILES

CN(CC1(C)CCCO1)S(=O)(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O

InChI Identifier

InChI=1S/C13H19ClN2O5S2/c1-13(6-3-7-21-13)9-16(2)23(19,20)10-4-5-11(14)12(8-10)22(15,17)18/h4-5,8H,3,6-7,9H2,1-2H3,(H2,15,17,18)

InChI Key

SMNOERSLNYGGOU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Tetrahydrofuran
Sulfonyl
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organosulfur compound
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)

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	1.32	ALOGPS
logP	0.94	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.86 m³·mol⁻¹	ChemAxon
Polarizability	36.06 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]+	182.521	30932474
DeepCCS	[M-H]-	180.163	30932474
DeepCCS	[M-2H]-	213.968	30932474
DeepCCS	[M+Na]+	189.463	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.6	32859911
AllCCS	[M+Na]+	185.3	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	177.4	32859911
AllCCS	[M+HCOO]-	178.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mefruside	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O	3897.8	Standard polar	33892256
Mefruside	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O	3032.4	Standard non polar	33892256
Mefruside	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O	3079.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mefruside,1TMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1	2984.0	Semi standard non polar	33892256
Mefruside,1TMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1	2947.6	Standard non polar	33892256
Mefruside,1TMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1	3856.3	Standard polar	33892256
Mefruside,2TMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2933.5	Semi standard non polar	33892256
Mefruside,2TMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3175.2	Standard non polar	33892256
Mefruside,2TMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3809.9	Standard polar	33892256
Mefruside,1TBDMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3253.3	Semi standard non polar	33892256
Mefruside,1TBDMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3210.7	Standard non polar	33892256
Mefruside,1TBDMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3901.5	Standard polar	33892256
Mefruside,2TBDMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3476.8	Semi standard non polar	33892256
Mefruside,2TBDMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3672.6	Standard non polar	33892256
Mefruside,2TBDMS,isomer #1	CN(CC1(C)CCCO1)S(=O)(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3863.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mefruside GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9230000000-3dae60c90061d10aff2f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mefruside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 40V, Positive-QTOF	splash10-001i-9130000000-636b02fdf0fc3e275768	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 80V, Positive-QTOF	splash10-001i-9100000000-9c1945a4bcea33e89926	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 20V, Positive-QTOF	splash10-003r-9870000000-eedb3b31f98777e26051	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 10V, Positive-QTOF	splash10-001i-3339000000-4276cabce9f9e5a77f6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 10V, Positive-QTOF	splash10-003r-9866000000-4e302ef0541f6714431d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 15V, Positive-QTOF	splash10-003r-9853000000-1d061894516a66508de0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 25V, Positive-QTOF	splash10-003r-9530000000-57194238f7e023316eb6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 80V, Positive-QTOF	splash10-001i-9100000000-e8aafdb307a26375ab14	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 20V, Positive-QTOF	splash10-003r-9640000000-c8d5afee5da34147caa6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 55V, Positive-QTOF	splash10-001i-9100000000-c4bd1a1dbe596766e279	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 50V, Positive-QTOF	splash10-001i-9110000000-ff5725b9dbe6b5402905	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 40V, Positive-QTOF	splash10-001i-9120000000-d6f2b4aac46b65b27ca0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 30V, Positive-QTOF	splash10-001i-9310000000-92d091f44ddb0e05c363	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 45V, Positive-QTOF	splash10-001i-9110000000-aec2e9b7e719382da4f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 40V, Positive-QTOF	splash10-001i-9200000000-110fea689fc0d7c1fb71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 65V, Positive-QTOF	splash10-001i-9200000000-1aa7c5eeaaa22253fabe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 60V, Positive-QTOF	splash10-001i-9200000000-78415f10385e4355cb9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 5V, Positive-QTOF	splash10-001i-9564000000-2b44c6ef26220f4e3880	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mefruside 70V, Positive-QTOF	splash10-001i-9200000000-e8bc58db90adb5ba7049	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mefruside 10V, Positive-QTOF	splash10-0002-9003000000-dce43ef0ade4f468bea9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mefruside 20V, Positive-QTOF	splash10-0002-9135000000-8f97fd0ef35270fb1f9e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mefruside 40V, Positive-QTOF	splash10-014j-9000000000-fe4f7d5da5ba42baa006	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mefruside 10V, Negative-QTOF	splash10-001i-1029000000-70e720cdec449cf80ea0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mefruside 20V, Negative-QTOF	splash10-0fai-7194000000-2fbab53a59ffc0386a18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mefruside 40V, Negative-QTOF	splash10-004i-9030000000-4b4771bb88d39385b210	2016-08-03	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

DB13405

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mefruside

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 Mefruside (HMDB0254410)

MOL for HMDB0254410 (Mefruside)

3D MOL for HMDB0254410 (Mefruside)

3D SDF for HMDB0254410 (Mefruside)

3D-SDF for HMDB0254410 (Mefruside)

PDB for HMDB0254410 (Mefruside)

3D PDB for HMDB0254410 (Mefruside)

SMILES for HMDB0254410 (Mefruside)

INCHI for HMDB0254410 (Mefruside)

Structure for HMDB0254410 (Mefruside)

3D Structure for HMDB0254410 (Mefruside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra