D-Biotin D-sulfoxide (ECMDB20288) (M2MDB001127)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-05-31 14:37:24 -0600
Update Date2015-06-03 17:19:42 -0600
Secondary Accession Numbers
  • ECMDB20288
Identification
Name:D-Biotin D-sulfoxide
DescriptionD-biotin d-sulfoxide is a member of the chemical class known as Biotin and Derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring. Biotin sulfoxide is the substance that is formed when biotin is exposed to ultraviolet light in the presence of oxygen. (WikiPedia)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 1H-thieno(3,4-D)Imidazole-4-pentanoate, hexahydro-2-oxo-, 5-oxide, (3as,4S,5S,6ar)-
  • 1H-thieno(3,4-D)Imidazole-4-pentanoate, hexahydro-2-oxo-, 5-oxide, (3as-(3aα,4β,5α,6aα))-
  • 1H-thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, 5-oxide, (3aS,4S,5S,6aR)-
  • 1H-thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, 5-oxide, (3aS-(3aα,4β,5α,6aα))-
  • Biotin sulfoxide
  • Biotin sulphoxide
  • D-Biotin D-sulphoxide
  • D-Biotin-D-sulfoxide
  • D-Biotin-D-sulphoxide
  • Hexahydro-2-oxo-5-oxide(3aS,4S,5S,6aR)-1H-Thieno(3,4-D)imidazole-4-pentanoate
  • Hexahydro-2-oxo-5-oxide(3aS,4S,5S,6aR)-1H-Thieno(3,4-D)imidazole-4-pentanoic acid
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4b,5a,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoate
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4b,5a,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoic acid
  • Hexahydro-2-oxo-5-oxide(3aS-(3aalpha,4beta,5alpha,6aalpha))-1H-Thieno(3,4-D)imidazole-4-pentanoate
  • Hexahydro-2-oxo-5-oxide(3aS-(3aalpha,4beta,5alpha,6aalpha))-1H-Thieno(3,4-D)imidazole-4-pentanoic acid
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4β,5α,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoate
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4β,5α,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoic acid
Chemical Formula:C10H16N2O4S
Weight:Average: 260.31
Monoisotopic: 260.0830777
InChI Key:KCSKCIQYNAOBNQ-YBSFLMRUSA-N
InChI:InChI=1S/C10H16N2O4S/c13-8(14)4-2-1-3-7-9-6(5-17(7)16)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-,17?/m0/s1
CAS number:10406-89-0
IUPAC Name:5-[(3aR,6S,6aS)-2-hydroxy-5-oxo-1H,3aH,4H,6H,6aH-5λ⁴-thieno[3,4-d]imidazol-6-yl]pentanoic acid
Traditional IUPAC Name:5-[(3aS,4S,6aR)-2-hydroxy-5-oxo-3H,3aH,4H,6H,6aH-5λ⁴-thieno[3,4-d]imidazol-4-yl]pentanoic acid
SMILES:[H][C@]12CS(=O)[C@@]([H])(CCCCC(O)=O)[C@@]1([H])NC(O)=N2
Chemical Taxonomy
Description belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBiotin and derivatives
Sub ClassNot Available
Direct ParentBiotin and derivatives
Alternative Parents
Substituents
  • Biotin_derivative
  • Biotin
  • Thienoimidazolidine
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Imidazolidinone
  • Fatty acid
  • Fatty acyl
  • Imidazolidine
  • Thiolane
  • Thiophene
  • Carbonic acid derivative
  • Sulfoxide
  • Urea
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.41 g/LALOGPS
logP-0.94ALOGPS
logP-2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)6.07ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area98.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.11 m³·mol⁻¹ChemAxon
Polarizability25.41 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
D-Biotin D-sulfoxide + Hydrogen ion + NADH > Biotin + Water + NAD
D-Biotin D-sulfoxide + Hydrogen ion + NADPH > Biotin + Water + NADP
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-f3a4d502612e8c7a7ab9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-3290000000-daa46a46142b7d70b3c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-7920000000-0641cab1071cddbf264fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-2490000000-db7d011b23b1ad94511dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-8390000000-8c08de9fdd8bd6719dc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-000f22c3d652c0a7bcd6View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID62193
HMDB IDNot Available
Pubchem Compound ID83833
Kegg IDC20386
ChemSpider ID75652
Wikipedia IDNot Available
BioCyc IDCPD-722
EcoCyc IDCPD-722

Enzymes

Protein Details
1. Biotin sulfoxide reductase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme may serve as a scavenger, allowing the cell to utilize biotin sulfoxide as a biotin source. It reduces a spontaneous oxidation product of biotin, D-biotin D-sulfoxide (BSO or BDS), back to biotin
Gene Name:
bisC
Uniprot ID:
P20099
Molecular weight:
85850