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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 04:13:50 UTC
Update Date2023-02-21 17:16:48 UTC
HMDB IDHMDB0003745
Secondary Accession Numbers
  • HMDB03745
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
Data?1676999808
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
Chemical FormulaC2H6O3S2
Average Molecular Weight142.197
Monoisotopic Molecular Weight141.975835438
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-1.5ALOGPS
logP-0.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.13 m³·mol⁻¹ChemAxon
Polarizability12.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.92431661259
DarkChem[M-H]-119.07431661259
DeepCCS[M+H]+128.030932474
DeepCCS[M-H]-125.96630932474
DeepCCS[M-2H]-161.56130932474
DeepCCS[M+Na]+135.97230932474
AllCCS[M+H]+131.832859911
AllCCS[M+H-H2O]+127.732859911
AllCCS[M+NH4]+135.532859911
AllCCS[M+Na]+136.632859911
AllCCS[M-H]-132.932859911
AllCCS[M+Na-2H]-136.832859911
AllCCS[M+HCOO]-141.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MesnaOS(=O)(=O)CCS2289.3Standard polar33892256
MesnaOS(=O)(=O)CCS1003.0Standard non polar33892256
MesnaOS(=O)(=O)CCS1355.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mesna,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)CCS1412.8Semi standard non polar33892256
Mesna,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)CCS1259.9Standard non polar33892256
Mesna,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)CCS1988.6Standard polar33892256
Mesna,1TMS,isomer #2C[Si](C)(C)SCCS(=O)(=O)O1511.3Semi standard non polar33892256
Mesna,1TMS,isomer #2C[Si](C)(C)SCCS(=O)(=O)O1374.8Standard non polar33892256
Mesna,1TMS,isomer #2C[Si](C)(C)SCCS(=O)(=O)O2380.6Standard polar33892256
Mesna,2TMS,isomer #1C[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C1587.9Semi standard non polar33892256
Mesna,2TMS,isomer #1C[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C1526.2Standard non polar33892256
Mesna,2TMS,isomer #1C[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C1902.4Standard polar33892256
Mesna,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS1699.5Semi standard non polar33892256
Mesna,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS1566.4Standard non polar33892256
Mesna,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS2117.4Standard polar33892256
Mesna,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCCS(=O)(=O)O1738.5Semi standard non polar33892256
Mesna,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCCS(=O)(=O)O1637.3Standard non polar33892256
Mesna,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCCS(=O)(=O)O2515.0Standard polar33892256
Mesna,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C(C)(C)C2088.3Semi standard non polar33892256
Mesna,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C(C)(C)C2032.4Standard non polar33892256
Mesna,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C(C)(C)C2076.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Mesna GC-MS (2 TMS)splash10-00e9-7960000000-d0e9fc5f5629ba893d572014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesna GC-MS (Non-derivatized)splash10-00e9-7960000000-d0e9fc5f5629ba893d572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesna GC-EI-TOF (Non-derivatized)splash10-052u-2900000000-51cd7c5f2497db0c7a152017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesna GC-EI-TOF (Non-derivatized)splash10-004m-7970000000-a5c3c33a78b251bdd12c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesna GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i0-9100000000-17bded3f4e78114bc0d32017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesna GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesna LC-ESI-QTOF , negative-QTOFsplash10-001i-9400000000-f69174f630c88b6e6c0b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 10V, Positive-QTOFsplash10-0006-1900000000-4ac0601c658b746cde742017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 20V, Positive-QTOFsplash10-03kc-8900000000-0f9ced3911873030886c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 40V, Positive-QTOFsplash10-03fr-9100000000-a5c85eeb5676f5fed8a52017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 10V, Negative-QTOFsplash10-001l-9600000000-b4d0e7498f823e6d5a042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 20V, Negative-QTOFsplash10-001i-9400000000-bc6293ab20fc276566eb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 40V, Negative-QTOFsplash10-001i-9100000000-9f5c132d4e221797ce202017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 10V, Positive-QTOFsplash10-00di-0900000000-77503e1563f802f72b032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 20V, Positive-QTOFsplash10-03di-9400000000-e948f4e89bfaaa610a8b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 40V, Positive-QTOFsplash10-03di-9000000000-82d53190c215e025c68b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 10V, Negative-QTOFsplash10-001i-9000000000-a6fb8cd4d3dc149be3092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 20V, Negative-QTOFsplash10-001l-9700000000-765d7a0589d47fc8bb0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesna 40V, Negative-QTOFsplash10-001i-9000000000-b4c0fc3315acedd6bf022021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09110
Phenol Explorer Compound IDNot Available
FooDB IDFDB023220
KNApSAcK IDC00000761
Chemspider ID578
KEGG Compound IDC03576
BioCyc IDCoM
BiGG IDNot Available
Wikipedia LinkCoenzyme M
METLIN IDNot Available
PubChem Compound598
PDB IDNot Available
ChEBI ID17905
Food Biomarker OntologyNot Available
VMH IDCOM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceJary, Jiri; Dolezal, Stanislav; Grossmann, Vojtech; Benes, Milan. Method of 2-mercaptoethanesulfonic acid production. Czech. (1988), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Duran M, Aarsen G, Fokkens RH, Nibbering NM, Cats BP, de Bree PK, Wadman SK: 2-Mercaptoethanesulfonate-cysteine disulfide excretion following the administration of 2-mercaptoethanesulfonate--a pitfall in the diagnosis of sulfite oxidase deficiency. Clin Chim Acta. 1981 Mar 19;111(1):47-53. [PubMed:6784974 ]
  2. Khaw SL, Downie PA, Waters KD, Ashley DM, Heath JA: Adverse hypersensitivity reactions to mesna as adjunctive therapy for cyclophosphamide. Pediatr Blood Cancer. 2007 Sep;49(3):341-3. [PubMed:16333822 ]
  3. Links M, Lewis C: Chemoprotectants: a review of their clinical pharmacology and therapeutic efficacy. Drugs. 1999 Mar;57(3):293-308. [PubMed:10193684 ]
  4. Goren MP: Oral mesna: a review. Semin Oncol. 1992 Dec;19(6 Suppl 12):65-71. [PubMed:1485175 ]