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Record Information
Version3.6
Creation Date2006-08-24 13:49:09 UTC
Update Date2017-03-02 21:27:37 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
D-AllobisnorbiotinMeSH
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 KeyQDFGCLSCEPNVQP-VPLCAKHXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDelta amino acids and derivatives
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Thia fatty acid
  • Fatty acyl
  • 2-imidazoline
  • Thiolane
  • Isourea
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid
  • Thioether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • 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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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. [PubMed: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. [PubMed:9039841 ]