Biotin (PAMDB000008)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000008
Identification
Name: Biotin
Description:Biotin 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. 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 acts as a carboxyl carrier in carboxylation reactions. 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. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (+)-Biotin
  • (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerate
  • (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid
  • (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerate
  • (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acid
  • -(+)-biotin
  • 1swk
  • 1swn
  • 1swr
  • 5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoate
  • 5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acid
  • d-biotin
  • Biodermatin
  • Bioepiderm
  • Bios
  • Bios h
  • Bios II
  • Biotin
  • Cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate
  • Cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid
  • Cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerate
  • Cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid
  • Cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerate
  • Cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acid
  • Coenzyme R
  • D(+)-Biotin
  • D-(+)-Biotin
  • D-Biotin
  • D-Biotin factor S
  • Delta-(+)-Biotin
  • Delta-Biotin
  • Delta-Biotin factor S
  • Factor S
  • Factor S (vitamin)
  • Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoate
  • Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acid
  • hexahydro-2-oxo-[3As-(3a,4b,6a)]-1H-thieno[3,4-D]imidazole-4-pentanoate
  • hexahydro-2-oxo-[3As-(3a,4b,6a)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid
  • Hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-D]imidazole-4-pentanoate
  • Hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-D]imidazole-4-pentanoic acid
  • Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-Thieno[3,4-D]imidazole-4-pentanoate
  • Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-Thieno[3,4-D]imidazole-4-pentanoic acid
  • hexahydro-2-oxo-[3As-(3α,4β,6α)]-1H-thieno[3,4-D]imidazole-4-pentanoate
  • hexahydro-2-oxo-[3As-(3α,4β,6α)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid
  • Lutavit H2
  • Meribin
  • Rovimix H 2
  • Vitamin B7
  • Vitamin H
  • Vitamin-h
  • δ-(+)-Biotin
  • δ-Biotin
  • δ-Biotin factor S
Chemical Formula: C10H16N2O3S
Average Molecular Weight: 244.311
Monoisotopic Molecular Weight: 244.088163078
InChI Key: YBJHBAHKTGYVGT-ZKWXMUAHSA-N
InChI: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
CAS number: 58-85-5
IUPAC Name:5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
Traditional IUPAC Name: biotin
SMILES:[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Biotin and derivatives
Sub ClassNot Available
Direct Parent Biotin and derivatives
Alternative Parents
Substituents
  • Biotin
  • Medium-chain fatty acid
  • Imidazolyl carboxylic acid derivative
  • Thia fatty acid
  • Heterocyclic fatty acid
  • Fatty acyl
  • Fatty acid
  • 2-imidazoline
  • Isourea
  • Azacycle
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular Framework Aliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 232 °C
Experimental Properties:
PropertyValueSource
Water Solubility:0.22 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
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
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
[2Fe-2S] iron-sulfur cluster + S-Adenosylmethionine + Dethiobiotin > [2Fe-1S] desulfurated iron-sulfur cluster + Biotin + 5'-Deoxyadenosine + Hydrogen ion + L-Methionine
D-Biotin D-sulfoxide + Hydrogen ion + NADH > Biotin + Water + NAD
D-Biotin D-sulfoxide + Hydrogen ion + NADPH > Biotin + Water + NADP
Adenosine triphosphate + Biotin <> Pyrophosphate + Biotinyl-5'-AMP
Dethiobiotin + Sulfur donor + 2 S-Adenosylmethionine + 2 e- + 2 Hydrogen ion <> Biotin +2 L-Methionine +2 5'-Deoxyadenosine
<i>S</i>-sulfanyl-[acceptor] + Dethiobiotin + S-Adenosylmethionine > an unsulfurated sulfur acceptor + Biotin + 5'-Deoxyadenosine + L-Methionine + Hydrogen ion
Benzo[a]pyrene-4,5-oxide + Red-Thioredoxin Biotin + Water + Ox-Thioredoxin
Adenosine triphosphate + Biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] > Adenosine monophosphate + Pyrophosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)]
Adenosine triphosphate + Biotin > Biotinyl-5'-AMP + Pyrophosphate
Biocytin + Water > Biotin + L-Lysine + L-Lysine
Dethiobiotin + 2 S-adenosyl-L-methionine + 2 Hydrogen ion + a sulfurated [sulfur carrier] > Biotin +2 L-Methionine +2 5'-Deoxyadenosine
Biotin Sulfoxide > Biotin
Biotin + Adenosine triphosphate > diphosphate + Biotinyl-5'-AMP + Pyrophosphate
Pathways:
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-MSNot Available
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
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
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
References
References:
  • Bigham SL, Ballard JD, Giles KD, Clelland CS, Jeffcoat R, Griffin KS, Farley TD, Bushman DR, Wright JR: Synthesis and possible applications of biotin-linked copper clusters. Physiol Chem Phys Med NMR. 1990;22(2):63-72. Pubmed: 2100006
  • Bingham JP, Bian S, Tan ZY, Takacs Z, Moczydlowski E: Synthesis of a biotin derivative of iberiotoxin: binding interactions with streptavidin and the BK Ca2+-activated K+ channel expressed in a human cell line. Bioconjug Chem. 2006 May-Jun;17(3):689-99. Pubmed: 16704206
  • Bussolati G, Gugliotta P, Volante M, Pace M, Papotti M: Retrieved endogenous biotin: a novel marker and a potential pitfall in diagnostic immunohistochemistry. Histopathology. 1997 Nov;31(5):400-7. Pubmed: 9416479
  • Fujimoto W, Inaoki M, Fukui T, Inoue Y, Kuhara T: Biotin deficiency in an infant fed with amino acid formula. J Dermatol. 2005 Apr;32(4):256-61. Pubmed: 15863846
  • Grafe F, Wohlrab W, Neubert RH, Brandsch M: Transport of biotin in human keratinocytes. J Invest Dermatol. 2003 Mar;120(3):428-33. Pubmed: 12603856
  • Gravel RA, Narang MA: Molecular genetics of biotin metabolism: old vitamin, new science. J Nutr Biochem. 2005 Jul;16(7):428-31. Pubmed: 15992684
  • Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. Pubmed: 15690449
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Limat A, Suormala T, Hunziker T, Waelti ER, Braathen LR, Baumgartner R: Proliferation and differentiation of cultured human follicular keratinocytes are not influenced by biotin. Arch Dermatol Res. 1996;288(1):31-8. Pubmed: 8750932
  • Mardach R, Zempleni J, Wolf B, Cannon MJ, Jennings ML, Cress S, Boylan J, Roth S, Cederbaum S, Mock DM: Biotin dependency due to a defect in biotin transport. J Clin Invest. 2002 Jun;109(12):1617-23. Pubmed: 12070309
  • Mock DM, Dyken ME: Biotin catabolism is accelerated in adults receiving long-term therapy with anticonvulsants. Neurology. 1997 Nov;49(5):1444-7. Pubmed: 9371938
  • Mock DM, Heird GM: Urinary biotin analogs increase in humans during chronic supplementation: the analogs are biotin metabolites. Am J Physiol. 1997 Jan;272(1 Pt 1):E83-5. Pubmed: 9038855
  • Mock DM, Nyalala JO, Raguseo RM: A direct streptavidin-binding assay does not accurately quantitate biotin in human urine. J Nutr. 2001 Aug;131(8):2208-14. Pubmed: 11481419
  • Mock DM, Stadler DD, Stratton SL, Mock NI: Biotin status assessed longitudinally in pregnant women. J Nutr. 1997 May;127(5):710-6. Pubmed: 9164991
  • Mock DM, Stadler DD: Conflicting indicators of biotin status from a cross-sectional study of normal pregnancy. J Am Coll Nutr. 1997 Jun;16(3):252-7. Pubmed: 9176832
  • Mock DM: Biotin status: which are valid indicators and how do we know? J Nutr. 1999 Feb;129(2S Suppl):498S-503S. Pubmed: 10064317
  • Mock NI, Malik MI, Stumbo PJ, Bishop WP, Mock DM: Increased urinary excretion of 3-hydroxyisovaleric acid and decreased urinary excretion of biotin are sensitive early indicators of decreased biotin status in experimental biotin deficiency. Am J Clin Nutr. 1997 Apr;65(4):951-8. Pubmed: 9094878
  • Schenker S, Hu ZQ, Johnson RF, Yang Y, Frosto T, Elliott BD, Henderson GI, Mock DM: Human placental biotin transport: normal characteristics and effect of ethanol. Alcohol Clin Exp Res. 1993 Jun;17(3):566-75. Pubmed: 8333586
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Thuy LP, Belmont J, Nyhan WL: Prenatal diagnosis and treatment of holocarboxylase synthetase deficiency. Prenat Diagn. 1999 Feb;19(2):108-12. Pubmed: 10215065
  • Thuy LP, Sweetman L, Nyhan WL: A new immunochemical assay for biotin. Clin Chim Acta. 1991 Oct 31;202(3):191-7. Pubmed: 1814646
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
  • Zempleni J: Uptake, localization, and noncarboxylase roles of biotin. Annu Rev Nutr. 2005;25:175-96. Pubmed: 16011464
Synthesis Reference: Corey, E. J.; Mehrotra, Mukund M. A simple and enantioselective synthesis of (+)-biotin. Tetrahedron Letters (1988), 29(1), 57-60.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15956
HMDB IDHMDB00030
Pubchem Compound ID171548
Kegg IDC00120
ChemSpider ID149962
WikipediaBiotin
BioCyc IDBIOTIN
EcoCyc IDBIOTIN
Ligand ExpoBTN

Enzymes

Protein Details
• Bifunctional protein BirA
General function:
Involved in biotin-[acetyl-CoA-carboxylase] ligase activity
Specific function:
BirA acts both as a biotin-operon repressor and as the enzyme that synthesizes the corepressor, acetyl-CoA:carbon-dioxide ligase. This protein also activates biotin to form biotinyl-5'- adenylate and transfers the biotin moiety to biotin-accepting proteins
Gene Name:
birA
Locus Tag:
PA4280
Molecular weight:
34 kDa
Reactions
ATP + biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] = AMP + diphosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)].
Protein Details
• Biotin synthase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dethiobiotin (DTB) to biotin by the insertion of a sulfur atom into dethiobiotin via a radical- based mechanism
Gene Name:
bioB
Locus Tag:
PA0500
Molecular weight:
39.1 kDa
Reactions
Dethiobiotin + sulfur + 2 S-adenosyl-L-methionine = biotin + 2 L-methionine + 2 5'-deoxyadenosine.

Transporters