1.0 2016-09-30 22:18:40 UTC 2020-06-04 20:42:57 UTC BMDB0000030 BMDB00030 Biotin Biotin, 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. (+)-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-valeric acid 5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acid Biotina Biotine Biotinum 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 Vitamin b7 Vitamin H Bioepiderm (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerate (3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerate 5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoate cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerate cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerate (+)-Biotin -(+)-Biotin 1SWK 1SWN 1SWR Biodermatin Bios H Bios II D(+)-Biotin D-Biotin factor S delta-(+)-Biotin delta-Biotin delta-Biotin factor S Factor S Factor S (vitamin) Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoate Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acid 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 Lutavit H2 Meribin Rovimix H 2 Vitamin-H 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 C10H16N2O3S 244.311 244.088163078 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid 58-85-5 [H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2 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 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 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. Organic compounds Organoheterocyclic compounds Biotin and derivatives Biotin and derivatives Azacyclic compounds Carbonyl compounds Carboximidamides Carboxylic acids Dialkylthioethers Heterocyclic fatty acids Hydrocarbon derivatives Imidazolines Imidazolyl carboxylic acids and derivatives Isoureas Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Thia fatty acids Thiolanes 2-imidazoline Aliphatic heteropolycyclic compound Azacycle Biotin Carbonyl group Carboximidamide Carboxylic acid Carboxylic acid derivative Dialkylthioether Fatty acid Fatty acyl Heterocyclic fatty acid Hydrocarbon derivative Imidazolyl carboxylic acid derivative Isourea Medium-chain fatty acid Monocarboxylic acid or derivatives Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Thia fatty acid Thioether Thiolane Aliphatic heteropolycyclic compounds Water-soluble vitamins biotins Solid melting_point 232 °C water_solubility 0.22 mg/mL at 25 °C logp 0.17 ALOGPS logs -2.30 ALOGPS logp 0.32 ChemAxon pka_strongest_acidic 4.4 ChemAxon pka_strongest_basic -1.9 ChemAxon iupac 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid ChemAxon average_mass 244.311 ChemAxon mono_mass 244.088163078 ChemAxon smiles [H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2 ChemAxon formula C10H16N2O3S ChemAxon inchi 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 ChemAxon inchikey YBJHBAHKTGYVGT-ZKWXMUAHSA-N ChemAxon polar_surface_area 78.43 ChemAxon refractivity 60.05 ChemAxon polarizability 24.92 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Alanine Metabolism SMP0087164 Ammonia Recycling SMP0087177 Biotin Metabolism SMP0087183 Citric Acid Cycle SMP0087163 Fatty Acid Biosynthesis SMP0087257 Gluconeogenesis SMP0087223 Glutamate Metabolism SMP0087169 LPS and Citrate Signaling and Inflammation SMP0120946 Propanoate Metabolism SMP0087248 Pyruvate Metabolism SMP0087231 Threonine and 2-Oxobutanoate Degradation SMP0087262 Transfer of Acetyl Groups into Mitochondria SMP0087254 Valine, Leucine, and Isoleucine Degradation SMP0087234 Warburg Effect SMP0087270 Specdb::EiMs 1972 Specdb::NmrTwoD 932 Specdb::NmrTwoD 936 Specdb::CMs 857 Specdb::CMs 1994 Specdb::CMs 3215 Specdb::CMs 30490 Specdb::CMs 30963 Specdb::CMs 37254 Specdb::CMs 130453 Specdb::CMs 138187 Specdb::CMs 1047151 Specdb::CMs 1047153 Specdb::CMs 1047155 Specdb::CMs 1047157 Specdb::CMs 1047158 Specdb::NmrOneD 1039 Specdb::NmrOneD 4827 Specdb::NmrOneD 4828 Specdb::NmrOneD 294995 Specdb::NmrOneD 294996 Specdb::NmrOneD 294997 Specdb::NmrOneD 294998 Specdb::NmrOneD 294999 Specdb::NmrOneD 295000 Specdb::NmrOneD 295001 Specdb::NmrOneD 295002 Specdb::NmrOneD 295003 Specdb::NmrOneD 295004 Specdb::NmrOneD 295005 Specdb::NmrOneD 295006 Specdb::NmrOneD 295007 Specdb::NmrOneD 295008 Specdb::NmrOneD 295009 Specdb::NmrOneD 295010 Specdb::NmrOneD 295011 Specdb::NmrOneD 295012 Specdb::NmrOneD 295013 Specdb::NmrOneD 295014 Specdb::MsMs 6162 Specdb::MsMs 6163 Specdb::MsMs 6164 Specdb::MsMs 6165 Specdb::MsMs 6166 Specdb::MsMs 6167 Specdb::MsMs 6168 Specdb::MsMs 6169 Specdb::MsMs 6170 Specdb::MsMs 179691 Specdb::MsMs 179692 Specdb::MsMs 179693 Specdb::MsMs 182025 Specdb::MsMs 182026 Specdb::MsMs 182027 Specdb::MsMs 374645 Specdb::MsMs 436925 Specdb::MsMs 436926 Specdb::MsMs 437350 Specdb::MsMs 437351 Specdb::MsMs 437352 Specdb::MsMs 437353 Specdb::MsMs 437354 Specdb::MsMs 438622 Specdb::MsMs 439629 All Tissues Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 0.041 uM 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 Milk 0.080 +/- 0.003 uM Quantified by LC-MS/MS in 1% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.097 +/- 0.004 uM Quantified by LC-MS/MS in 2% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.090 +/- 0.003 uM Quantified by LC-MS/MS in 3.25% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.090 +/- 0.002 uM Quantified by LC-MS/MS in skim milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.086 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.041 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.082 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.078 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.082 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.082 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.064 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.041 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00120 DB00121 149962 171548 15956 FDB014510 BIOTIN C00000756 Biotin 33931 243 Corey, E. J.; Mehrotra, Mukund M. A simple and enantioselective synthesis of (+)-biotin. Tetrahedron Letters (1988), 29(1), 57-60. 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 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00204 Acetyl-CoA carboxylase 1 Q9TTS3 ACACA Enzyme BMDBP00615 Pyruvate carboxylase, mitochondrial Q29RK2 PC Enzyme BMDBP00822 Pyruvate carboxylase Q861T5 Enzyme BMDBP01240 Biotinidase A6QQ07 BTD Enzyme BMDBP02007 PCCA protein A4FV90 PCCA Enzyme BMDBP02008 Acetyl-CoA carboxylase, type beta Q50I03 acacb Enzyme BMDBP02009 Acetyl-CoA carboxylase, type beta Q50I04 acacb Enzyme BMDBP02876 LOC534247 protein A8E662 LOC534247 Enzyme