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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2021-09-14 15:19:56 UTC
HMDB IDHMDB0059664
Secondary Accession Numbers
  • HMDB59664
Metabolite Identification
Common NameOxidized dithiothreitol
DescriptionOxidized dithiothreitol, also known as dithiane diol, belongs to the class of organic compounds known as dithianes. Dithianes are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres. Oxidized dithiothreitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxidized dithiothreitol exists in all living organisms, ranging from bacteria to humans. oxidized dithiothreitol can be biosynthesized from 1,4-dithiothreitol; which is mediated by the enzyme vitamin K epoxide reductase complex subunit 1. In humans, oxidized dithiothreitol is involved in vitamin k metabolism. Oxidized dithiothreitol is part of the Ubiquinone and other terpenoid-quinone biosynthesis pathway.
Structure
Data?1563865962
Synonyms
ValueSource
DITHIANE diolChEBI
Chemical FormulaC4H8O2S2
Average Molecular Weight152.235
Monoisotopic Molecular Weight151.99657088
IUPAC Name(4R,5R)-1,2-dithiane-4,5-diol
Traditional Namedithiane diol
CAS Registry NumberNot Available
SMILES
O[C@H]1CSSC[C@@H]1O
InChI Identifier
InChI=1S/C4H8O2S2/c5-3-1-7-8-2-4(3)6/h3-6H,1-2H2/t3-,4-/m0/s1
InChI KeyYPGMOWHXEQDBBV-IMJSIDKUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dithianes. Dithianes are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithianes
Sub ClassNot Available
Direct ParentDithianes
Alternative Parents
Substituents
  • 1,2-dithiane
  • Secondary alcohol
  • Organic disulfide
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Process

Naturally occurring process

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 Solubility70.5 g/LALOGPS
logP10(-0.44) g/LALOGPS
logP10(-0.59) g/LChemAxon
logS10(-0.33) g/LALOGPS
pKa (Strongest Acidic)13.48ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.27 m³·mol⁻¹ChemAxon
Polarizability14.2 ųChemAxon
Number of Rings1ChemAxon
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]+129.77831661259
DarkChem[M-H]-124.91831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oxidized dithiothreitolO[C@H]1CSSC[C@@H]1O2345.5Standard polar33892256
Oxidized dithiothreitolO[C@H]1CSSC[C@@H]1O1286.7Standard non polar33892256
Oxidized dithiothreitolO[C@H]1CSSC[C@@H]1O1469.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxidized dithiothreitol,1TMS,isomer #1C[Si](C)(C)O[C@H]1CSSC[C@@H]1O1498.2Semi standard non polar33892256
Oxidized dithiothreitol,2TMS,isomer #1C[Si](C)(C)O[C@H]1CSSC[C@@H]1O[Si](C)(C)C1565.4Semi standard non polar33892256
Oxidized dithiothreitol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CSSC[C@@H]1O1767.1Semi standard non polar33892256
Oxidized dithiothreitol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CSSC[C@@H]1O[Si](C)(C)C(C)(C)C2020.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxidized dithiothreitol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-54e6035f9875a201a7d12017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxidized dithiothreitol GC-MS (2 TMS) - 70eV, Positivesplash10-00ei-9540000000-2e61f9be80be5f76b4032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxidized dithiothreitol 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 - Oxidized dithiothreitol 10V, Positive-QTOFsplash10-0udi-0900000000-622c1b7429e88053c00f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 20V, Positive-QTOFsplash10-0udi-3900000000-0f52b0d04bffe421fe3c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 40V, Positive-QTOFsplash10-014i-5900000000-956f0ff12fe55a46f4e12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 10V, Negative-QTOFsplash10-0zfr-2900000000-6f1fa5f15faccfb8b0fd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 20V, Negative-QTOFsplash10-00di-9200000000-53723104744b637cbc1b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 40V, Negative-QTOFsplash10-0006-9000000000-06e2d9a14b171c6803eb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 10V, Negative-QTOFsplash10-0udl-8900000000-f79cebe8184593326db92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 20V, Negative-QTOFsplash10-0229-9100000000-51e26c89a14acf2718252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 40V, Negative-QTOFsplash10-0ab9-9000000000-154ea92ffa4b7dd57eb92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 10V, Positive-QTOFsplash10-0f89-0900000000-9d158d9dcd42330f9ffb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 20V, Positive-QTOFsplash10-0ufr-9800000000-e16768009745316a92932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxidized dithiothreitol 40V, Positive-QTOFsplash10-0005-9000000000-f587e73e7f197f3b3fec2021-09-23Wishart 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 IDDB01822
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID388524
KEGG Compound IDC01119
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439407
PDB IDDTD
ChEBI ID42147
Food Biomarker OntologyNot Available
VMH IDDTTOX
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
Reactions
Phylloquinol + Oxidized dithiothreitol → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails
Vitamin K1 + Oxidized dithiothreitol + Water → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails
Vitamin K + Oxidized dithiothreitol + Water → Vitamin K epoxide + 1,4-Dithiothreitoldetails
2,3-Epoxymenaquinone + 1,4-Dithiothreitol → Menatetrenone + Oxidized dithiothreitol + Waterdetails