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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:55:52 UTC
Update Date2022-03-07 02:57:15 UTC
HMDB IDHMDB0042046
Secondary Accession Numbers
  • HMDB42046
Metabolite Identification
Common NameTreosulfan
DescriptionTreosulfan, also known as DHB or dihydroxybusulfan, belongs to the class of organic compounds known as organosulfonic acid esters. These are esters of sulfonic acid, which have the general structure RS(=O)2OR' (R,R' = organyl, not H). Based on a literature review very few articles have been published on Treosulfan.
Structure
Data?1563863725
Synonyms
ValueSource
TreosulphanGenerator
(2S,3S)-Threitol 1,4-bismethanesulfonateHMDB
1,4-Dimethanesulfonate(2S,3S)-threitolHMDB
1,4-Dimethanesulfonatel-(+ )-threitolHMDB
1,4-Dimethanesulfonatel-threitolHMDB
DHBHMDB
DihydroxybusulfanHMDB
DihydroxymyleranHMDB
L-Threitol 1,4-dimethanesulfonateHMDB
L-Threitol, 1, 4-bis(methanesulfonate)HMDB
L-Threitol-1, 4-bis(methanesulfonate)HMDB
L-Threitol-1,4-bis(methanesulfonate)HMDB
L-Threityl dimesylateHMDB
TresulfanHMDB
Treosulfan, (r*,s*)-isomerHMDB
Treosulfan, (R-(r*,r*))-isomerHMDB
Treosulfan, ((r*,r*)-(+-))-isomerHMDB
Treosulfan, (r*,r*)-isomerHMDB
L-DihydroxybusulfanHMDB
L-Threitol-1,4-bismethanesulfonateHMDB
2,3-Dihydroxy-4-(methanesulfonyloxy)butyl methanesulfonic acidHMDB
2,3-Dihydroxy-4-(methanesulphonyloxy)butyl methanesulphonateHMDB
2,3-Dihydroxy-4-(methanesulphonyloxy)butyl methanesulphonic acidHMDB
TreosulfanMeSH
Chemical FormulaC6H14O8S2
Average Molecular Weight278.301
Monoisotopic Molecular Weight278.013008804
IUPAC Name2,3-dihydroxy-4-(methanesulfonyloxy)butyl methanesulfonate
Traditional Nametreosulfan
CAS Registry Number299-75-2
SMILES
CS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O
InChI Identifier
InChI=1S/C6H14O8S2/c1-15(9,10)13-3-5(7)6(8)4-14-16(2,11)12/h5-8H,3-4H2,1-2H3
InChI KeyYCPOZVAOBBQLRI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfonic acid esters. These are esters of sulfonic acid, which have the general structure RS(=O)2OR' (R,R' = organyl, not H).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acid esters
Alternative Parents
Substituents
  • Organosulfonic acid ester
  • Sulfonic acid ester
  • Sulfonyl
  • Methanesulfonate
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility17 g/LALOGPS
logP-1.5ALOGPS
logP-2.6ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.99ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.2 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.98 m³·mol⁻¹ChemAxon
Polarizability24.61 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]+162.85431661259
DarkChem[M-H]-155.30331661259
DeepCCS[M+H]+148.32130932474
DeepCCS[M-H]-145.96330932474
DeepCCS[M-2H]-179.82230932474
DeepCCS[M+Na]+154.58430932474
AllCCS[M+H]+159.132859911
AllCCS[M+H-H2O]+155.932859911
AllCCS[M+NH4]+161.932859911
AllCCS[M+Na]+162.832859911
AllCCS[M-H]-152.132859911
AllCCS[M+Na-2H]-153.032859911
AllCCS[M+HCOO]-154.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TreosulfanCS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O4605.1Standard polar33892256
TreosulfanCS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O1604.3Standard non polar33892256
TreosulfanCS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O2256.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Treosulfan,1TMS,isomer #1C[Si](C)(C)OC(COS(C)(=O)=O)C(O)COS(C)(=O)=O2133.5Semi standard non polar33892256
Treosulfan,2TMS,isomer #1C[Si](C)(C)OC(COS(C)(=O)=O)C(COS(C)(=O)=O)O[Si](C)(C)C2156.9Semi standard non polar33892256
Treosulfan,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(COS(C)(=O)=O)C(O)COS(C)(=O)=O2368.5Semi standard non polar33892256
Treosulfan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(COS(C)(=O)=O)C(COS(C)(=O)=O)O[Si](C)(C)C(C)(C)C2612.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Treosulfan GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2910000000-7b870a14b1617dd5f13f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Treosulfan GC-MS (2 TMS) - 70eV, Positivesplash10-08or-9144100000-e1ca3fdcf6d66c408f3b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Treosulfan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Treosulfan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 10V, Positive-QTOFsplash10-004i-0290000000-df280d54c803c5bc66c32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 20V, Positive-QTOFsplash10-00v3-1930000000-4bf0f20ffa5b2dd46a462015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 40V, Positive-QTOFsplash10-059b-6900000000-f4a4a07a9dd21c8f4e452015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 10V, Negative-QTOFsplash10-004i-3690000000-1a343f8ec1bd0c60c6122015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 20V, Negative-QTOFsplash10-004i-9310000000-606ef41892f23d8f38d12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 40V, Negative-QTOFsplash10-004i-9000000000-11d09c630882cc1994232015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 10V, Negative-QTOFsplash10-004i-0090000000-83942a1596793b3d1b512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 20V, Negative-QTOFsplash10-0006-9530000000-bd28e97da8fb58dd368a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 40V, Negative-QTOFsplash10-002g-9100000000-194525da464d3a5b8de52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 10V, Positive-QTOFsplash10-004i-0090000000-7d83f8d3328a4ea6fe3c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 20V, Positive-QTOFsplash10-01r2-9810000000-fa72124aad09d46948692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Treosulfan 40V, Positive-QTOFsplash10-0002-9200000000-3c0132ee253b502bcecf2021-09-23Wishart 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
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8937
KEGG Compound IDC19557
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTreosulfan
METLIN IDNot Available
PubChem Compound9296
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available