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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:03 UTC
HMDB IDHMDB0001458
Secondary Accession Numbers
  • HMDB01458
Metabolite Identification
Common NameBiotin amide
DescriptionThe enzyme biotinidase (EC-Number 3.5.1.12 ) is involved in the recycling of the vitamin biotin, cleaving D-biotinylamides and esters, in a reaction including biotin amide and water. (PMID 1719240 , 171927 ). Late-onset multiple carboxylase deficiency (MCD) with biotinidase deficiency is caused by mutation in the biotinidase gene. MCD is an autosomal recessive metabolic disorder characterized primarily by cutaneous and neurologic abnormalities. Symptoms result from the patient's inability to reutilize biotin, a necessary nutrient. (OMIM 253260 ).
Structure
Thumb
Synonyms
ValueSource
5-[(3AS,6R,6ar)-2-hydroxy-1H,3ah,4H,6H,6ah-thieno[3,4-D]imidazol-6-yl]pentanimidateGenerator, HMDB
Chemical FormulaC10H17N3O2S
Average Molecular Weight243.326
Monoisotopic Molecular Weight243.104147493
IUPAC Name5-[(3aR,4R,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamide
Traditional Name5-[(3aR,4R,6aS)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamide
CAS Registry Number6929-42-6
SMILES
[H][C@@]12CS[C@H](CCCCC(N)=O)[C@]1([H])NC(=O)N2
InChI Identifier
InChI=1S/C10H17N3O2S/c11-8(14)4-2-1-3-7-9-6(5-16-7)12-10(15)13-9/h6-7,9H,1-5H2,(H2,11,14)(H2,12,13,15)/t6-,7-,9-/m1/s1
InChI KeyXFLVBMBRLSCJAI-ZXFLCMHBSA-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_derivative
  • Thienoimidazolidine
  • Fatty amide
  • Imidazolidinone
  • Fatty acyl
  • Thiophene
  • Thiolane
  • Imidazolidine
  • Carboxamide group
  • Urea
  • Primary carboxylic acid amide
  • Carbonic acid derivative
  • Azacycle
  • Dialkylthioether
  • Thioether
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022636
KNApSAcK IDNot Available
Chemspider ID388677
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439597
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTsuboi, Toshinori; Akagi, Chihiro; Yoshimura, Yoshio; Shoji, Osamu. Microbial preparation of biotinamide. Jpn. Tokkyo Koho (1971), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yoshimoto K, Rosenfeld S, Frickhofen N, Kennedy D, Hills R, Kajigaya S, Young NS: A second neutralizing epitope of B19 parvovirus implicates the spike region in the immune response. J Virol. 1991 Dec;65(12):7056-60. [PubMed:1719240 ]
  2. Marsh JM: The role of cyclic AMP in gonadal function. Adv Cyclic Nucleotide Res. 1975;6:137-99. [PubMed:171927 ]

Enzymes

General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Catalytic release of biotin from biocytin, the product of biotin-dependent carboxylases degradation.
Gene Name:
BTD
Uniprot ID:
P43251
Molecular weight:
61132.43
Reactions
Biotin amide + Water → Biotin + Ammoniadetails