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Record Information
Version3.6
Creation Date2006-08-24 13:49:09 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04821
Secondary Accession NumbersNone
Metabolite Identification
Common NameBisnorbiotin
DescriptionBisnorbiotin is a natural biotin metabolite in human urine. (PMID 9039841 ). The urinary excretion of Bisnorbiotin a increased with biotin administration. (PMID 9022537 ).
Structure
Thumb
Synonyms
ValueSource
hexahydro-2-oxo-1H-thieno[3,4-D]Imidazole-4-propionic acidHMDB
[3AS-(3aa,4b,6aa)]-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-propanoateHMDB
[3AS-(3aa,4b,6aa)]-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-propanoic acidHMDB
Chemical FormulaC8H12N2O3S
Average Molecular Weight216.257
Monoisotopic Molecular Weight216.05686295
IUPAC Name3-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]propanoic acid
Traditional Name3-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]propanoic acid
CAS Registry Number16968-98-2
SMILES
[H][C@]12CS[C@@H](CCC(O)=O)[C@@]1([H])NC(=O)N2
InChI Identifier
InChI=1S/C8H12N2O3S/c11-6(12)2-1-5-7-4(3-14-5)9-8(13)10-7/h4-5,7H,1-3H2,(H,11,12)(H2,9,10,13)/t4-,5-,7-/m0/s1
InChI KeyInChIKey=QDFGCLSCEPNVQP-VPLCAKHXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thienoimidazolidines. These are heterocyclic compounds containing a thiophene ring fused to an imidazolidine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Imidazolidine is 5-membered saturated ring of three carbon atoms, and two nitrogen centers at the 1- and 3-positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThienoimidazolidines
Sub ClassNot Available
Direct ParentThienoimidazolidines
Alternative Parents
Substituents
  • Thienoimidazolidine
  • Thia fatty acid
  • Fatty acyl
  • Imidazolidinone
  • Thiophene
  • Imidazolidine
  • Urea
  • Azacycle
  • Dialkylthioether
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility3.19 mg/mLALOGPS
logP-0.76ALOGPS
logP-0.57ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.85 m3·mol-1ChemAxon
Polarizability20.68 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00018 (0.00002-0.00059) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.003 (0.0003-0.0057) uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0063 (0.0004-0.017) uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0044 (0.0013-0.0076) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023429
KNApSAcK IDNot Available
Chemspider ID78006
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04821
Metagene LinkHMDB04821
METLIN ID7083
PubChem Compound86492
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot 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. [9022537 ]
  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. [9039841 ]