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Record Information
Version1.0
Creation Date2016-07-13 19:22:16 UTC
Update Date2016-09-23 18:44:27 UTC
LmdbLMDB00009
Secondary Accession NumbersNone
Metabolite Identification
Common NameBiotin
DescriptionBiotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the 'biotin cycle'. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various animal tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in animal histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology. (PMID: 15992684 , 16011464 ).
Structure
Thumb
Synonyms
ValueSource
(+)-cis-hexahydro-2-oxo-1H-thieno[3,4]Imidazole-4-valeric acidChEBI
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acidChEBI
5-(2-oxohexahydro-1H-thieno[3,4-D]Imidazol-4-yl)pentanoic acidChEBI
BiotinaChEBI
BiotineChEBI
BiotinumChEBI
cis-(+)-tetrahydro-2-oxothieno[3,4]Imidazoline-4-valeric acidChEBI
cis-hexahydro-2-oxo-1H-thieno(3,4)Imidazole-4-valeric acidChEBI
cis-tetrahydro-2-oxothieno(3,4-D)Imidazoline-4-valeric acidChEBI
Coenzyme RChEBI
D-(+)-BiotinChEBI
D-BiotinChEBI
Vitamin b7ChEBI
Vitamin HChEBI
(+)-cis-hexahydro-2-oxo-1H-thieno[3,4]Imidazole-4-valerateGenerator
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerateGenerator
5-(2-oxohexahydro-1H-thieno[3,4-D]Imidazol-4-yl)pentanoateGenerator
cis-(+)-tetrahydro-2-oxothieno[3,4]Imidazoline-4-valerateGenerator
cis-hexahydro-2-oxo-1H-thieno(3,4)Imidazole-4-valerateGenerator
cis-tetrahydro-2-oxothieno(3,4-D)Imidazoline-4-valerateGenerator
(+)-BiotinHMDB
-(+)-BiotinHMDB
1SWKHMDB
1SWNHMDB
1SWRHMDB
BiodermatinHMDB
BioepidermHMDB
Bios HHMDB
Bios IIHMDB
D(+)-BiotinHMDB
D-Biotin factor SHMDB
delta-(+)-BiotinHMDB
delta-BiotinHMDB
delta-Biotin factor SHMDB
Factor SHMDB
Factor S (vitamin)HMDB
hexahydro-2-oxo-1H-thieno(3,4-D)Imidazole-4-pentanoateHMDB
hexahydro-2-oxo-1H-thieno(3,4-D)Imidazole-4-pentanoic acidHMDB
hexahydro-2-oxo-[3AS-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
hexahydro-2-oxo-[3AS-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
hexahydro-2-oxo-[3As-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
hexahydro-2-oxo-[3As-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
Lutavit H2HMDB
MeribinHMDB
Rovimix H 2HMDB
Vitamin-HHMDB
Biotin hermes brandMeSH
Biotin roche brandMeSH
Biotin simons brandMeSH
Biotin strathmann brandMeSH
Biotin ziethen brandMeSH
Biotin ratiopharmMeSH
Roche brand OF biotinMeSH
Roche, biotineMeSH
E+b pharma brand OF biotinMeSH
MedobiotinMeSH
BiokurMeSH
BiotinratiopharmMeSH
Gelfert, biotinMeSH
Hermes brand OF biotinMeSH
Hermes, biotinMeSH
Medopharm brand OF biotinMeSH
Ratiopharm brand OF biotinMeSH
Biocur brand OF biotinMeSH
Biotin dermapharm brandMeSH
Biotine rocheMeSH
DeacuraMeSH
Dermapharm brand OF biotinMeSH
GabunatMeSH
MedebiotinMeSH
RombellinMeSH
Ziethen brand OF biotinMeSH
Biotin biocur brandMeSH
Biotin gelfertMeSH
Biotin hermesMeSH
Biotin medopharm brandMeSH
Biotin ratiopharm brandMeSH
Biotin-ratiopharmMeSH
H, VitaminMeSH
Medea brand OF biotin sodium saltMeSH
Simons brand OF biotinMeSH
Strathmann brand OF biotinMeSH
Chemical FormulaC10H16N2O3S
Average Molecular Weight244.311
Monoisotopic Molecular Weight244.088163078
IUPAC Name5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
Traditional Namebiotin
CAS Registry Number58-85-5
SMILES
[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
InChI Identifier
InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
InChI KeyYBJHBAHKTGYVGT-ZKWXMUAHSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Imidazolyl carboxylic acid derivative
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Thiolane
  • 2-imidazoline
  • Isourea
  • Azacycle
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Thioether
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.17ALOGPS
logP0.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.05 m3·mol-1ChemAxon
Polarizability24.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0f76-1960000000-b21ddd69490cac3254f8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f76-3960000000-a8a94e2de123f66979d8View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0006-6910000000-11bfe0a5a77f7dfaa8c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f76-1960000000-b21ddd69490cac3254f8View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0f76-3960000000-a8a94e2de123f66979d8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00dl-9680000000-eb01d8147a82f7982b54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0090000000-6d956bb533d353d449c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0190000000-01f67d1bdf8c742e48c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-107f2a44f521c2513578View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a3f65d909dc40055e87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0090000000-c928e8d0a18f3f848262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-066s-1920000000-5f795e0b7f1d7cf986e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0ar1-1920000000-c298be862857cb3bbc7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000t-0900000000-cdc4a4c359ff765fd32dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05xs-1920000000-3be430b63e9c748c681aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090000000-bcffb0dcf77e8fd727a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6x-0390000000-c209523d36e9a7681f44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0090000000-c0f81ee86772310db415View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0190000000-016eb89528e564c74720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9400000000-107f2a44f521c2513578View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d08e1b3709844e1e91b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0190000000-21d0f2512788276bbb89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0690000000-dc372934024e58bdcc60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0290000000-43932f104dea28cbdfb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1960000000-d3673c6bc624b97f35beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-00a4e152d89024a9b423View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1390000000-3f4b512cfa57b894ff94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6y-7890000000-ea1e647fc5b31e42af0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e139c928dcc46b225bdbView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected and Quantified0.02 mg/kgNot AvailableBovine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified0.0093 mg/kgNot AvailableOvine
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified0.015 mg/kgNot AvailableCaprine
    • Park, Y. W; Juáre...
details
DrugBank IDDB00121
HMDB IDHMDB00030
FooDB IDFDB014510
Phenol Explorer IDNot Available
KNApSAcK IDC00000756
BiGG ID33931
BioCyc IDBIOTIN
METLIN ID243
PDB IDBTN
Wikipedia LinkBiotin
Chemspider ID149962
ChEBI ID15956
PubChem Compound ID171548
Kegg Compound IDC00120
YMDB IDNot Available
ECMDB IDECMDB00030
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gravel RA, Narang MA: Molecular genetics of biotin metabolism: old vitamin, new science. J Nutr Biochem. 2005 Jul;16(7):428-31. [15992684 ]
  2. Zempleni J: Uptake, localization, and noncarboxylase roles of biotin. Annu Rev Nutr. 2005;25:175-96. [16011464 ]