Showing metabocard for Mesna (MMDBc0049989)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:47:42 UTC
Update Date2024-10-11 00:48:05 UTC
Metabolite IDMMDBc0049989
Metabolite Identification
Common NameMesna
DescriptionMesna is a chemoprotectant. Chemoprotectants have been developed as a means of ameliorating the toxicity associated with cytotoxic agents by providing site-specific protection for normal tissues, without compromising antitumour efficacy. Mesna eliminates the risk of therapy-limiting urotoxic side effects of oxazaphosphorines. Mesna is widely used for the prevention of cyclophosphamide-related hemorrhagic cystitis. It has been associated with hypersensitivity-like cutaneous and systemic reactions in adult patients. Mesna offers significant uroprotection in patients receiving high dose cyclophosphamide, and is widely used in paediatric oncology practice It is, therefore, important to recognize that it may be associated with a rare but significant systemic adverse reaction. A hypersensitivity-like reaction to mesna was first reported in a young adult receiving treatment for Hodgkin disease over 20 years ago. Oral administration of mesna can facilitate outpatient ifosfamide therapy. Blood and urinary mesna concentrations are more steady and prolonged after oral delivery compared with after intravenous delivery. (PMID: 16333822 , 10193684 , 1485175 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb586e1438>


  Mrv0541 02231219472D          

  7  6  0  0  0  0            999 V2000
   23.7719  -10.7753    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.9153  -10.3628    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0574  -11.1878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3594  -10.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1844  -11.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4864  -10.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2009  -10.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb586e1438>

HMDB0003745
     RDKit          3D
Mesna
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.1605   -1.4715    0.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171   -0.6612   -0.4773 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.6009   -1.2316   -1.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4852    0.9242   -0.7258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -0.6691    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    0.1410    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    1.8412   -0.2752 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2653    1.1696   -0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -0.3169    1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.7139    0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705   -0.3424   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3938    0.0523    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    2.2784    0.5490 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  5  9  1  0
  5 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb586e1438>


  Mrv0541 02231219472D          

  7  6  0  0  0  0            999 V2000
   23.7719  -10.7753    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.9153  -10.3628    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0574  -11.1878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3594  -10.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1844  -11.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4864  -10.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2009  -10.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049989

> <DATABASE_NAME>
MIME

> <SMILES>
OS(=O)(=O)CCS

> <INCHI_IDENTIFIER>
InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)

> <INCHI_KEY>
ZNEWHQLOPFWXOF-UHFFFAOYSA-N

> <FORMULA>
C2H6O3S2

> <MOLECULAR_WEIGHT>
142.197

> <EXACT_MASS>
141.975835438

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.536652175043326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-sulfanylethane-1-sulfonic acid

> <ALOGPS_LOGP>
-1.53

> <JCHEM_LOGP>
-0.40282442733333357

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.11818943963675

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.1570374648504043

> <JCHEM_PKA_STRONGEST_BASIC>
-9.606739922099255

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
29.130200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
HS-CoM

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb586e1438>

HMDB0003745
     RDKit          3D
Mesna
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.1605   -1.4715    0.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171   -0.6612   -0.4773 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.6009   -1.2316   -1.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4852    0.9242   -0.7258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -0.6691    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    0.1410    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    1.8412   -0.2752 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2653    1.1696   -0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -0.3169    1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.7139    0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705   -0.3424   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3938    0.0523    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    2.2784    0.5490 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  5  9  1  0
  5 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
M  END
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PDB for #<Metabolite:0x00007fdb586e1438>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      44.374 -20.114   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      48.375 -19.344   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      43.040 -20.884   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      43.604 -18.780   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      45.144 -21.448   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      45.708 -19.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.042 -20.114   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    6                                             
CONECT    2    7                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1    7                                                       
CONECT    7    2    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for #<Metabolite:0x00007fdb586e1438>

COMPND    HMDB0003745
HETATM    1  O1  UNL     1       2.160  -1.472   0.077  1.00  0.00           O  
HETATM    2  S1  UNL     1       1.017  -0.661  -0.477  1.00  0.00           S  
HETATM    3  O2  UNL     1       0.601  -1.232  -1.793  1.00  0.00           O  
HETATM    4  O3  UNL     1       1.485   0.924  -0.726  1.00  0.00           O  
HETATM    5  C1  UNL     1      -0.333  -0.669   0.664  1.00  0.00           C  
HETATM    6  C2  UNL     1      -1.463   0.141   0.047  1.00  0.00           C  
HETATM    7  S2  UNL     1      -0.967   1.841  -0.275  1.00  0.00           S  
HETATM    8  H1  UNL     1       2.265   1.170  -0.160  1.00  0.00           H  
HETATM    9  H2  UNL     1      -0.062  -0.317   1.657  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.707  -1.714   0.748  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.671  -0.342  -0.942  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.394   0.052   0.632  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.068   2.278   0.549  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4    8
CONECT    5    6    9   10
CONECT    6    7   11   12
CONECT    7   13
END
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SMILES for #<Metabolite:0x00007fdb586e1438>

OS(=O)(=O)CCS
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INCHI for #<Metabolite:0x00007fdb586e1438>

InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)
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Synonyms
ValueSource
1-THIOETHANEsulfonIC ACIDChEBI
2-MercaptoethanesulfonateChEBI
2-Mercaptoethanesulfonic acidChEBI
2-Mercaptoethanesulphonic acidChEBI
2-MercaptoethylsulfonateChEBI
2-SulfanylethylsulfonateChEBI
beta-Mercaptoethanesulfonic acidChEBI
Coenzima mChEBI
Coenzym mChEBI
CoMChEBI
HS-CoMChEBI
MesnaChEBI
Reduced coenzyme mChEBI
Reduced comChEBI
1-THIOETHANEsulfonateGenerator
1-THIOETHANEsulphonateGenerator
1-THIOETHANEsulphonic acidGenerator
2-MercaptoethanesulphonateGenerator
2-Mercaptoethylsulfonic acidGenerator
2-MercaptoethylsulphonateGenerator
2-Mercaptoethylsulphonic acidGenerator
2-Sulfanylethylsulfonic acidGenerator
2-SulphanylethylsulphonateGenerator
2-Sulphanylethylsulphonic acidGenerator
b-MercaptoethanesulfonateGenerator
b-Mercaptoethanesulfonic acidGenerator
b-MercaptoethanesulphonateGenerator
b-Mercaptoethanesulphonic acidGenerator
beta-MercaptoethanesulfonateGenerator
beta-MercaptoethanesulphonateGenerator
beta-Mercaptoethanesulphonic acidGenerator
Β-mercaptoethanesulfonateGenerator
Β-mercaptoethanesulfonic acidGenerator
Β-mercaptoethanesulphonateGenerator
Β-mercaptoethanesulphonic acidGenerator
Coenzyme mHMDB
2 MercaptoethanesulfonateMeSH, HMDB
ASTA D 7093MeSH, HMDB
Kendrick brand OF mesnaMeSH, HMDB
MistabronMeSH, HMDB
MistabroncoMeSH, HMDB
Sodium 2-mercaptoethanesulphonateMeSH, HMDB
UCB brand OF mesnaMeSH, HMDB
Cell pharm brand OF mesnaMeSH, HMDB
ASTA-D 7093MeSH, HMDB
ASTAD 7093MeSH, HMDB
Bristol myers squibb brand OF mesnaMeSH, HMDB
MESNA-cellMeSH, HMDB
MucofluidMeSH, HMDB
Sanfer brand OF mesnaMeSH, HMDB
ZikenMeSH, HMDB
2-Mercaptoethanesulphonate, sodiumMeSH, HMDB
ASTA medica brand OF mesnaMeSH, HMDB
Mesna kendrick brandMeSH, HMDB
Mesna sanfer brandMeSH, HMDB
MesnexMeSH, HMDB
MesnumMeSH, HMDB
MitexanMeSH, HMDB
Bristol-myers squibb brand OF mesnaMeSH, HMDB
MESNA cellMeSH, HMDB
UromitexanMeSH, HMDB
Molecular FormulaC2H6O3S2
Average Mass142.197
Monoisotopic Mass141.975835438
IUPAC Name2-sulfanylethane-1-sulfonic acid
Traditional NameHS-CoM
CAS Registry Number3375-50-6
SMILES
OS(=O)(=O)CCS
InChI Identifier
InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)
InChI KeyZNEWHQLOPFWXOF-UHFFFAOYSA-N