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Record Information
Version1.0
Creation Date2016-09-30 22:18:40 UTC
Update Date2020-06-04 20:42:57 UTC
BMDB IDBMDB0000030
Secondary Accession Numbers
  • BMDB00030
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 NameNot Available
Traditional NameNot Available
CAS Registry Number58-85-5
SMILESNot Available
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 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
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • All Tissues
  • Liver
  • Milk
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.041 uMNot SpecifiedNot SpecifiedNormal
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified0.080 +/- 0.003 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.097 +/- 0.004 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.090 +/- 0.003 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.090 +/- 0.002 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.086 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.041 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.082 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.078 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.082 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.082 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.064 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.041 uMNot SpecifiedNot Specified
Normal
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000030
DrugBank IDDB00121
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
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]

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Cytosolic enzyme that catalyzes the carboxylation of acetyl-CoA to malonyl-CoA, the first and rate-limiting step of de novo fatty acid biosynthesis. This is a 2 steps reaction starting with the ATP-dependent carboxylation of the biotin carried by the biotin carboxyl carrier (BCC) domain followed by the transfer of the carboxyl group from carboxylated biotin to acetyl-CoA.
Gene Name:
ACACA
Uniprot ID:
Q9TTS3
Molecular weight:
265303.0
General function:
Involved in ATP binding
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate (By similarity).
Gene Name:
PC
Uniprot ID:
Q29RK2
Molecular weight:
129698.0
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q861T5
Molecular weight:
16309.0
General function:
Involved in biotinidase activity
Specific function:
Catalytic release of biotin from biocytin, the product of biotin-dependent carboxylases degradation.
Gene Name:
BTD
Uniprot ID:
A6QQ07
Molecular weight:
58353.0
Reactions
Biocytin + Water → Biotin + L-Lysinedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
PCCA
Uniprot ID:
A4FV90
Molecular weight:
81718.0
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
acacb
Uniprot ID:
Q50I03
Molecular weight:
42349.0
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
acacb
Uniprot ID:
Q50I04
Molecular weight:
23669.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
LOC534247
Uniprot ID:
A8E662
Molecular weight:
80134.0
Reactions
Adenosine triphosphate + Biotin → Biotinyl-5'-AMP + Pyrophosphatedetails