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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]imidazolidin-4-yl]pentanoic acid
Traditional IUPAC Namebiotin
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
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