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Human Metabolome Database Version 3.5

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Showing metabocard for Biotin sulfone (HMDB04818)

Record Information
Version 3.5
Creation Date 2006-08-24 07:39:46 -0600
Update Date 2013-02-08 17:13:22 -0700
HMDB ID HMDB04818
Secondary Accession Numbers None
Metabolite Identification
Common Name Biotin sulfone
Description Biotin sulfone is a natural biotin metabolite in human urine. (PMID 9039841 Link_out). The urinary excretion of biotin sulfone a increased with biotin administration. (PMID 9022537 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5,5-Dioxide Biotin
  2. [3aS-(3aa,4b,6aa)]- 5,5-dioxide-hexahydro-2-oxo-1H-Thieno[3,4-D]imidazole-4-pentanoate
  3. [3aS-(3aa,4b,6aa)]- 5,5-dioxide-hexahydro-2-oxo-1H-Thieno[3,4-D]imidazole-4-pentanoic acid
Chemical Formula C10H16N2O5S
Average Molecular Weight 276.309
Monoisotopic Molecular Weight 276.077992322
IUPAC Name 5-[(3aS,4S,6aR)-2,5,5-trioxo-hexahydro-1H-5$l^{6},1,3-[1$l^{6}]thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
Traditional IUPAC Name 5-[(3aS,4S,6aR)-2,5,5-trioxo-hexahydro-5$l^{6},1,3-[1$l^{6}]thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
CAS Registry Number 40720-05-6
SMILES [H][C@]12CS(=O)(=O)[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
InChI Identifier InChI=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 Key QPFQYMONYBAUCY-ZKWXMUAHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteropolycyclic Compounds
Class Thienoimidazolidines
Sub Class Biotin and Derivatives
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Heterocyclic Fatty Acids
  • Thia Fatty Acids
Substituents
  • Carboxylic Acid
  • Imidazolidine
  • Imidazolidinone
  • Sulfone
  • Sulfoxide
  • Thiolane
  • Urea
Direct Parent Biotin and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 16.1 g/L ALOGPS
LogP -1.06 ALOGPS
LogP -1.2 ChemAxon
LogS -1.23 ALOGPS
pKa (strongest acidic) 3.86 ChemAxon
pKa (strongest basic) -1.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 112.57 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 60.44 ChemAxon
Polarizability 26.24 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.00032 (0.00-0.00065) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023428
KNApSAcK ID Not Available
Chemspider ID 75678 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04818 Link_out
Metagene Link HMDB04818 Link_out
METLIN ID 7082 Link_out
PubChem Compound 83863 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not 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. Pubmed: 9022537 Link_out