Biotin sulfone (CHEM021671)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:38 UTC
Update Date2026-04-06 12:52:04 UTC
Accession NumberCHEM021671
Identification
Common NameBiotin sulfone
ClassSmall Molecule
DescriptionBiotin sulfone is a natural biotin metabolite in human urine. (PMID 9039841). The urinary excretion of biotin sulfone a increased with biotin administration. (PMID 9022537).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5,5-Dioxide biotinChEBI
[3AS-(3aa,4b,6aa)]-5,5-dioxide-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acidChEBI
[3AS-(3aa,4b,6aa)]-5,5-dioxide-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoateGenerator
Biotin sulphoneGenerator
5-((3AS,4S,6ar)-5,5-dioxido-2-oxohexahydro-1H-thieno(3,4-D)imidazol-4-yl)pentanoic acidMeSH
[3AS-(3aa,4b,6aa)]- 5,5-dioxide-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
[3AS-(3aa,4b,6aa)]- 5,5-dioxide-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
Chemical FormulaC10H16N2O5S
Average Molecular Mass276.309 g/mol
Monoisotopic Mass276.078 g/mol
CAS Registry Number40720-05-6
IUPAC Name5-[(3aS,4S,6aR)-2,5,5-trioxo-hexahydro-1H-5λ⁶-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
Traditional Name5-[(3aS,4S,6aR)-2,5,5-trioxo-hexahydro-5λ⁶-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
SMILES[H][C@]12CS(=O)(=O)[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
InChI IdentifierInChI=1S/C10H16N2O5S/c13-8(14)4-2-1-3-7-9-6(5-18(7,16)17)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
InChI KeyQPFQYMONYBAUCY-ZKWXMUAHSA-N
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
  • Imidazolyl carboxylic acid derivative
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Fatty acid
  • Fatty acyl
  • 2-imidazoline
  • Sulfone
  • Thiolane
  • Isourea
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-1.1ALOGPS
logP-1.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.44 m³·mol⁻¹ChemAxon
Polarizability26.24 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9440000000-1c52a504c730b15049b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-6970000000-30089da78cf0ca4f5efaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0090000000-c44a2d9a678137742bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-2790000000-73413860cfdb8bf97ca7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0043-9620000000-d431dda06f942c88bb29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2390000000-adaa3c0f7ad790361a80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052g-9340000000-f26b2be172eef38fc87bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ee2350bbdc53d81139e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-c08757af0593294271eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0190000000-6e408e98cc5ac169b089Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-5d1f8e0280a38b7bf585Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-014d3cba016fc21f50edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090000000-2d6335dc30bf7a96f43cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-5490000000-d899e19c8e3d05d6dcc1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004818
FooDB IDFDB023428
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7084
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13628421
ChEBI ID89480
PubChem Compound ID21252323
Kegg Compound IDC20387
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zempleni J, McCormick DB, Mock DM: Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-l-sulfoxide in human urine. Am J Clin Nutr. 1997 Feb;65(2):508-11.
2. Mock DM, Wang KS, Kearns GL: The pig is an appropriate model for human biotin catabolism as judged by the urinary metabolite profile of radioisotope-labeled biotin. J Nutr. 1997 Feb;127(2):365-9.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=13510484
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14350781
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18141516
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18788729
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20985652
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=9022537