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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:42 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 through its interaction with 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
Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility70.5 g/LALOGPS
logP-0.44ALOGPS
logP-0.59ChemAxon
logS-0.33ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-54e6035f9875a201a7d1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ei-9540000000-2e61f9be80be5f76b403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-622c1b7429e88053c00fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-0f52b0d04bffe421fe3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5900000000-956f0ff12fe55a46f4e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-2900000000-6f1fa5f15faccfb8b0fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9200000000-53723104744b637cbc1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-06e2d9a14b171c6803ebSpectrum
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
FoodDB 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
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