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Record Information
Version1.0
Creation Date2016-09-30 22:18:40 UTC
Update Date2019-02-05 19:56:54 UTC
MCDB ID BMDB00030
Secondary Accession NumbersNone
Metabolite Identification
Common NameBiotin
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 a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Biotin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Biotin exists in all living species, ranging from bacteria to humans. In cattle, biotin is involved in the metabolic pathway called the biotin metabolism pathway. Biotin is a potentially toxic compound.
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
BioepidermKegg
(+)-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
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 brandHMDB
Biotin roche brandHMDB
Biotin simons brandHMDB
Biotin strathmann brandHMDB
Biotin ziethen brandHMDB
Biotin ratiopharmHMDB
Roche brand OF biotinHMDB
Roche, biotineHMDB
E+b pharma brand OF biotinHMDB
MedobiotinHMDB
BiokurHMDB
BiotinratiopharmHMDB
Gelfert, biotinHMDB
Hermes brand OF biotinHMDB
Hermes, biotinHMDB
Medopharm brand OF biotinHMDB
Ratiopharm brand OF biotinHMDB
Biocur brand OF biotinHMDB
Biotin dermapharm brandHMDB
Biotine rocheHMDB
DeacuraHMDB
Dermapharm brand OF biotinHMDB
GabunatHMDB
MedebiotinHMDB
RombellinHMDB
Ziethen brand OF biotinHMDB
Biotin biocur brandHMDB
Biotin gelfertHMDB
Biotin hermesHMDB
Biotin medopharm brandHMDB
Biotin ratiopharm brandHMDB
Biotin-ratiopharmHMDB
H, VitaminHMDB
Medea brand OF biotin sodium saltHMDB
Simons brand OF biotinHMDB
Strathmann brand OF biotinHMDB
Chemical FormulaC10H16N2O3S
Average Molecular Weight244.311
Monoisotopic Molecular Weight244.088163078
IUPAC Name5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
Traditional Name5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
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
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
Experimental Properties
PropertyValueReference
Melting Point232 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.22 mg/mL at 25 °CNot 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 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
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 | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9680000000-eb01d8147a82f7982b54JSpectraViewer | MoNA
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 | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1960000000-d3673c6bc624b97f35beJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-00a4e152d89024a9b423JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1390000000-3f4b512cfa57b894ff94JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6y-7890000000-ea1e647fc5b31e42af0bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e139c928dcc46b225bdbJSpectraViewer | MoNA
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
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.1 uM details
Detected and Quantified0.041 uM details
Detected and Quantified0.082 uM details
Detected and Quantified0.078 uM details
Detected and Quantified0.082 uM details
Detected and Quantified0.082 uM details
Detected and Quantified0.064 uM details
Detected and Quantified0.041 uM details
Detected and Quantified0.041 uM
  • Park, Y. W; Juáre...
details
Detected and Quantified0.080 +/- 0.003 uM details
Detected and Quantified0.097 +/- 0.004 uM details
Detected and Quantified0.090 +/- 0.003 uM details
Detected and Quantified0.090 +/- 0.002 uM details
HMDB IDHMDB0000030
DrugBank IDDB00121
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014510
KNApSAcK IDC00000756
Chemspider ID149962
KEGG Compound IDC00120
BioCyc IDBIOTIN
BiGG ID33931
Wikipedia LinkBiotin
METLIN ID243
PubChem Compound171548
PDB IDNot Available
ChEBI ID15956
References
Synthesis ReferenceCorey, 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)
General References
  1. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  2. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  3. Fooddata+, The Technical University of Denmark (DTU) [Link]