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Identification
YMDB IDYMDB00282
NameBiotin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionBiotin, also known as D-biotin or biotin ratiopharm, 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. Biotin is an extremely weak basic (essentially neutral) compound (based on its pKa). Biotin exists in all living species, ranging from bacteria to humans. Biotin is a potentially toxic compound.
Structure
Thumb
Synonyms
  • -(+)-biotin
  • (+)-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
  • 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
  • Biodermatin
  • Bioepiderm
  • 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-valeric acid
  • cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid
  • Coenzyme R
  • D-(+)-biotin
  • d-Biotin
  • D-biotin factor s
  • D(+)-Biotin
  • delta-(+)-Biotin
  • delta-Biotin
  • delta-biotin factor s
  • Factor s
  • 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-1H-thieno(3,4-d)imidazole-4-pentanoate
  • Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoic acid
  • Lutavit H2
  • Meribin
  • Rovimix H 2
  • Vitamin B7
  • Vitamin H
  • Vitamin-h
  • Biotina
  • Biotine
  • Biotinum
  • cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerate
  • cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerate
  • Factor S (vitamin)
  • Biotin hermes brand
  • Biotin roche brand
  • Biotin simons brand
  • Biotin strathmann brand
  • Biotin ziethen brand
  • Biotin ratiopharm
  • Roche brand OF biotin
  • Roche, biotine
  • E+b pharma brand OF biotin
  • Medobiotin
  • Biokur
  • Biotinratiopharm
  • Gelfert, biotin
  • Hermes brand OF biotin
  • Hermes, biotin
  • Medopharm brand OF biotin
  • Ratiopharm brand OF biotin
  • Biocur brand OF biotin
  • Biotin dermapharm brand
  • Biotine roche
  • Deacura
  • Dermapharm brand OF biotin
  • Gabunat
  • Medebiotin
  • Rombellin
  • Ziethen brand OF biotin
  • Biotin biocur brand
  • Biotin gelfert
  • Biotin hermes
  • Biotin medopharm brand
  • Biotin ratiopharm brand
  • Biotin-ratiopharm
  • H, Vitamin
  • Medea brand OF biotin sodium salt
  • Simons brand OF biotin
  • Strathmann brand OF biotin
CAS number58-85-5
WeightAverage: 244.311
Monoisotopic: 244.088163078
InChI KeyYBJHBAHKTGYVGT-ZKWXMUAHSA-N
InChIInChI=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
IUPAC Name5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
Traditional IUPAC Name5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
Chemical FormulaC10H16N2O3S
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]1([H])SC([H])([H])[C@]2([H])N([H])C(=O)N([H])[C@]12[H]
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
  • 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
Physical Properties
StateSolid
Charge0
Melting point232 °C
Experimental Properties
PropertyValueReference
Water Solubility0.22 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
LogP.PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.05 m³·mol⁻¹ChemAxon
Polarizability24.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Biotin BiosynthesisPW002380 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biotin metabolismec00780 Map00780
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
Dethiobiotin + S-Adenosyl-L-methionine + Reduced ferredoxin + a sulfurated [sulfur carrier]  → Biotin + L-Methionine + 5'-Deoxyadenosine + an unsulfurated [sulfur carrier] + Oxidized ferredoxin
KEGG Reactions
polysulfur + DethiobiotinBiotin + hydron
Adenosine triphosphate + Biotin + hydronPyrophosphate + Biotinyl-5'-AMP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f76-1960000000-b21ddd69490cac3254f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f76-3960000000-a8a94e2de123f66979d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f76-1960000000-b21ddd69490cac3254f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f76-3960000000-a8a94e2de123f66979d8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6910000000-11bfe0a5a77f7dfaa8c5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9680000000-eb01d8147a82f7982b54JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0090000000-6d956bb533d353d449c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0190000000-01f67d1bdf8c742e48c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-107f2a44f521c2513578JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a3f65d909dc40055e87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0090000000-c928e8d0a18f3f848262JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-066s-1920000000-5f795e0b7f1d7cf986e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0ar1-1920000000-c298be862857cb3bbc7fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000t-0900000000-cdc4a4c359ff765fd32dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05xs-1920000000-3be430b63e9c748c681aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090000000-bcffb0dcf77e8fd727a4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6x-0390000000-c209523d36e9a7681f44JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0090000000-c0f81ee86772310db415JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0190000000-016eb89528e564c74720JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9400000000-107f2a44f521c2513578JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d08e1b3709844e1e91b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0190000000-21d0f2512788276bbb89JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0690000000-dc372934024e58bdcc60JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0290000000-43932f104dea28cbdfb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1960000000-d3673c6bc624b97f35beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-00a4e152d89024a9b423JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1390000000-3f4b512cfa57b894ff94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6y-7890000000-ea1e647fc5b31e42af0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e139c928dcc46b225bdbJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-01pt-9500000000-a1e1ec56cf32236ac6b1JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Muhlenhoff, U., Gerl, M. J., Flauger, B., Pirner, H. M., Balser, S., Richhardt, N., Lill, R., Stolz, J. (2007). "The ISC [corrected] proteins Isa1 and Isa2 are required for the function but not for the de novo synthesis of the Fe/S clusters of biotin synthase in Saccharomyces cerevisiae." Eukaryot Cell 6:495-504.17259550
  • Wu, H., Ito, K., Shimoi, H. (2005). "Identification and characterization of a novel biotin biosynthesis gene in Saccharomyces cerevisiae." Appl Environ Microbiol 71:6845-6855.16269718
  • Hoja, U., Wellein, C., Greiner, E., Schweizer, E. (1998). "Pleiotropic phenotype of acetyl-CoA-carboxylase-defective yeast cells--viability of a BPL1-amber mutation depending on its readthrough by normal tRNA(Gln)(CAG)." Eur J Biochem 254:520-526.9688262
Synthesis Reference:Corey, E. J.; Mehrotra, Mukund M. A simple and enantioselective synthesis of (+)-biotin. Tetrahedron Letters (1988), 29(1), 57-60.
External Links:
ResourceLink
CHEBI ID15956
HMDB IDHMDB00030
Pubchem Compound ID171548
Kegg IDC00120
ChemSpider ID149962
FOODB IDFDB014510
WikipediaBiotin
BioCyc IDBIOTIN

Enzymes

General function:
Involved in catalytic activity
Specific function:
Dethiobiotin + sulfur + 2 S-adenosyl-L- methionine = biotin + 2 L-methionine + 2 5'-deoxyadenosine
Gene Name:
BIO2
Uniprot ID:
P32451
Molecular weight:
41883.80078
Reactions
Dethiobiotin + sulfur + 2 S-adenosyl-L-methionine → biotin + 2 L-methionine + 2 5'-deoxyadenosine.
General function:
Involved in biotin-[acetyl-CoA-carboxylase] ligase activity
Specific function:
Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl- CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-methylcrotonyl CoA carboxylase
Gene Name:
BPL1
Uniprot ID:
P48445
Molecular weight:
76362.39844
Reactions
ATP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxytransferase] → AMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxytransferase].
ATP + biotin + apo-[propionyl-CoA:carbon-dioxide ligase (ADP-forming)] → AMP + diphosphate + [propionyl-CoA:carbon-dioxide ligase (ADP-forming)].
ATP + biotin + apo-[3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)] → AMP + diphosphate + [3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)].
ATP + biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] → AMP + diphosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)].

Transporters

General function:
Involved in transmembrane transport
Specific function:
Involved in uptake of biotin with the concomitant entry of protons
Gene Name:
VHT1
Uniprot ID:
P53241
Molecular weight:
69082.10156