Record Information
Version1.0
Creation date2010-04-08 22:11:19 UTC
Update date2018-05-29 01:12:37 UTC
Primary IDFDB014510
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBiotin
DescriptionPresent in many foods; particularly rich sources include yeast, eggs, liver, certain fish (e.g. mackerel, salmon, sardines), soybeans, cauliflower and cow peas. Dietary supplement. Isolated from various higher plant sources, e.g. sweet corn seedlings and radish leaves Biotin D(+) is a cofactor responsible for carbon dioxide transfer in several carboxylase enzymes:; Biotin binds very tightly to the tetrameric protein avidin (also streptavidin and neutravidin), with a dissociation constant Kd in the order of 10?15 mol/L which is one of the strongest known protein-ligand interactions, approaching the covalent bond in strength. This is often used in different biotechnological applications. Until 2005, very harsh conditions were required to break the biotin-streptavidin bond.; Biotin is a water-soluble B-complex vitamin which is composed of an ureido ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; 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 and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. 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 deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. 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. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys 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. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various human tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; Biotin, also known as vitamin H or B7, is a water-soluble B-complex vitamin which is composed of an ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is a cofactor in the metabolism of fatty acids and leucine, and it plays a role in gluconeogenesis.; Signs of Biotin Deficiency: In general, appetite and growth are decreased. Dermatologic symptoms include dermatitis, alopecia (hair loss) and achromotrichia (absence or loss of pigment in the hair.) Perosis (a shortening and thickening of bones) is seen in the skeleton. Fatty Liver and Kidney Syndrome (FLKS) and hepatic steatosis also can occur. Genetic defect could also cause biotin deficiency. Holocarboxylase synthetase deficiency is a genetic mutation. It is a severe metabolic disorder. Biochemical and clinical manifestation includes: ketolactic acidosis, organic aciduria, hyperammonemia, skin rash, feeding problems, hypotonie, seizures, development delay, alopecia, and coma. This disease is lethal, however, mentioned manifestation can be reversed by pharmacologic doses of biotin (10-100 mg per day).[citation needed]; at least seven biotinylation sites have been identified in human histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology. (PMID: 15992684, 16011464)
CAS Number58-85-5
Structure
Thumb
Synonyms
SynonymSource
-(+)-biotinbiospider
(+)-biotinbiospider
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeratebiospider
(+)-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-valerateGenerator
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acidChEBI
1avdbiospider
1ndjbiospider
1stpbiospider
1swgbiospider
1swkbiospider
1swnbiospider
1swpbiospider
1swrbiospider
2avibiospider
3H-Biotinbiospider
5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoatebiospider
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acidChEBI
Beta-biotinbiospider
Biodermatinbiospider
Bioepidermbiospider
Bioepiderm (TN)biospider
Bios hbiospider
Bios IIbiospider
Biotin (8CI)biospider
Biotin (jan/usp/inn)biospider
Biotin [usan:inn:jan]biospider
Biotin 50 Mcgbiospider
Biotin111Inbiospider
BiotinaChEBI
BiotineChEBI
Biotinumbiospider
BTNbiospider
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeratebiospider
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acidChEBI
cis-hexahydro-2-oxo-1H-thieno(3,4)Imidazole-4-valerateGenerator
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acidbiospider
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerateGenerator
cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acidbiospider
Coenzyme Rdb_source
D-(+)-biotinbiospider
D-biotinbiospider
D-biotin factor sbiospider
D(+)-biotinbiospider
Delta-(+)-biotinbiospider
Delta-biotinbiospider
Delta-biotin factor sbiospider
Factor sbiospider
Factor s (vitamin)biospider
Factor S?db_source
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
Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoatebiospider
Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoic acidbiospider
Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid, 9CIdb_source
Injacom hbiospider
Lutavit H2biospider
Medebiotinbiospider
Meribinbiospider
Ritatinbiospider
Rovimix H 2biospider
Vitamin B7db_source
Vitamin BWbiospider
Vitamin Hdb_source
Vitamin h (van)biospider
Vitamin-hbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP0.3ALOGPS
logP-0.39ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)-3.4ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.57 m³·mol⁻¹ChemAxon
Polarizability25.35 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16N2O3S
IUPAC name5-{2-hydroxy-1H,3aH,4H,6H,6aH-thieno[3,4-d]imidazol-6-yl}pentanoic acid
InChI IdentifierInChI=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)
InChI KeyYBJHBAHKTGYVGT-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCCC1SCC2NC(=O)NC12
Average Molecular Weight244.311
Monoisotopic Molecular Weight244.088163078
Classification
DescriptionThis compound belongs to the class of chemical entities known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBiotin and derivatives
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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 49.16%; H 6.60%; N 11.47%; O 19.65%; S 13.12%DFC
Melting PointMp 232-233°DFC
Boiling PointNot Available
Experimental Water Solubility0.22 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge-1
Optical Rotation[a]20D +91 (c, 1 in 0.1M NaOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0190000000-400804991d4b8776fe84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2980000000-68076f6a2c987bd92f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-40dbd261db19fa5865dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-8d6e8764cae3cb06c427View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9570000000-361e42779e39f7c3fcc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-066b93fae869213887c3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01pt-9500000000-a1e1ec56cf32236ac6b1View in MoNA
ChemSpider ID149962
ChEMBL IDCHEMBL857
KEGG Compound IDC00120
Pubchem Compound ID171548
Pubchem Substance IDNot Available
ChEBI ID15956
Phenol-Explorer IDNot Available
DrugBank IDDB00121
HMDB IDHMDB00030
CRC / DFC (Dictionary of Food Compounds) IDJRM31-Z:JRM31-Z
EAFUS ID337
Dr. Duke IDBIOTIN
BIGG ID33931
KNApSAcK IDC00000756
HET IDBTN
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBiotin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti seborrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
Enzymes
NameGene NameUniProt ID
Propionyl-CoA carboxylase beta chain, mitochondrialPCCBP05166
BiotinidaseBTDP43251
Propionyl-CoA carboxylase alpha chain, mitochondrialPCCAP05165
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrialMCCC2Q9HCC0
Biotin--protein ligaseHLCSP50747
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrialMCCC1Q96RQ3
Pathways
NameSMPDB LinkKEGG Link
Biotin MetabolismSMP00066 map00780
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).