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Record Information
Version	2.0
Creation Date	2012-05-31 14:37:24 -0600
Update Date	2015-06-03 17:19:42 -0600
Secondary Accession Numbers	ECMDB20288
Identification
Name:	D-Biotin D-sulfoxide
Description	D-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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xad2170fc> Close
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.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Biotin and derivatives
Sub Class	Not Available
Direct Parent	Biotin and derivatives
Alternative Parents	Thienoimidazolidines Medium-chain fatty acids Heterocyclic fatty acids Imidazolidinones Thiophenes Thiolanes Ureas Sulfoxides Sulfinyl compounds Azacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organonitrogen compounds Carbonyl compounds Organopnictogen compounds
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 Framework	Aliphatic heteropolycyclic compounds
External Descriptors	sulfoxide (CHEBI:62193 ) biotins (CHEBI:62193 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 6.41 g/L ALOGPS logP -0.94 ALOGPS logP -2 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 3.58 ChemAxon pKa (Strongest Basic) 6.07 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 98.99 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 62.11 m³·mol⁻¹ ChemAxon Polarizability 25.41 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-0090000000-f3a4d502612e8c7a7ab9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0296-3290000000-daa46a46142b7d70b3c7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0089-7920000000-0641cab1071cddbf264f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4j-2490000000-db7d011b23b1ad94511d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00kf-8390000000-8c08de9fdd8bd6719dc2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9100000000-000f22c3d652c0a7bcd6 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 62193 HMDB ID Not Available Pubchem Compound ID 83833 Kegg ID C20386 ChemSpider ID 75652 Wikipedia ID Not Available BioCyc ID CPD-722 EcoCyc ID CPD-722

Enzymes