Showing metabocard for Dethiobiotin (BMDB0003581)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:27 UTC
Update Date2020-04-22 15:12:33 UTC
BMDB IDBMDB0003581
Secondary Accession Numbers
  • BMDB03581
Metabolite Identification
Common NameDethiobiotin
DescriptionDethiobiotin belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on Dethiobiotin.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-DethiobiotinChEBI
(4R,5S)-5-Methyl-2-oxo-4-imidazolidinehexanoic acidChEBI
(4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoic acidChEBI
D-DethiobiotinChEBI
DesthiobiotinChEBI
(4R,5S)-5-Methyl-2-oxo-4-imidazolidinehexanoateGenerator
(4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoateGenerator
Desthiobiotin, (4R-cis)-isomerMeSH
Desthiobiotin, (cis)-(+-)-isomerMeSH
4-Methyl-5-(omega-carboxyamyl)imidazolidone-2HMDB
4-Methyl-5-(ω-carboxyamyl)imidazolidone-2HMDB
5-Methyl-2-oxo-4-imidazolidinecaproic acidHMDB
DethiobiotinHMDB
epsilon-(4-Methyl-5-imidazolidone-2)caproic acidHMDB
ε-(4-Methyl-5-imidazolidone-2)caproic acidHMDB
Chemical FormulaC10H18N2O3
Average Molecular Weight214.2615
Monoisotopic Molecular Weight214.131742452
IUPAC Name6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid
Traditional Name(4R,5S)-dethiobiotin
CAS Registry Number533-48-2
SMILES
[H][C@@]1(C)NC(=O)N[C@]1([H])CCCCCC(O)=O
InChI Identifier
InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1
InChI KeyAUTOLBMXDDTRRT-JGVFFNPUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Imidazolidinone
  • Imidazolidine
  • Carbonic acid derivative
  • Urea
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point157 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.72ALOGPS
logP0.73ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.63ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity54.4 m³·mol⁻¹ChemAxon
Polarizability23.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003581
DrugBank IDDB03775
Phenol Explorer Compound IDNot Available
FooDB IDFDB023201
KNApSAcK IDC00000757
Chemspider ID392787
KEGG Compound IDC01909
BioCyc IDDETHIOBIOTIN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3351
PubChem Compound445027
PDB IDNot Available
ChEBI ID42280
References
Synthesis ReferenceKuzuhara, Hiroyoshi; Ohrui, Hiroshi; Emoto, Sakae. Syntheses with azido sugars. II. Conversion of D-glucose to (+)-dethiobiotin. Agricultural and Biological Chemistry (1971), 35(1), 8-17.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available