1.0 2016-09-30 22:31:10 UTC 2020-05-11 20:47:23 UTC BMDB0000468 BMDB00468 Biopterin (-)-Biopterin (1'r,1's) Biopterin 2-Amino-6-(L-erythro-1,2-dihydroxypropyl)-4(3H)-pteridinone 6-Biopterin L-Biopterin L-Erythro-biopterin Pterin H b2 [S-(R*,s*)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone Orinapterin Dictyopterin 2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone Biopterin C9H11N5O3 237.2153 237.086189243 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-8H-pteridin-4-one 22150-76-1 C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1 InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1 LHQIJBMDNUYRAM-DZSWIPIPSA-N belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. Organic compounds Organoheterocyclic compounds Pteridines and derivatives Pterins and derivatives Biopterins and derivatives 1,2-diols Aminopyrimidines and derivatives Aromatic alcohols Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines Pyrazines Pyrimidones Secondary alcohols Vinylogous amides 1,2-diol Alcohol Amine Aminopyrimidine Aromatic alcohol Aromatic heteropolycyclic compound Azacycle Biopterin Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Pyrazine Pyrimidine Pyrimidone Secondary alcohol Vinylogous amide Aromatic heteropolycyclic compounds biopterin Solid water_solubility 0.7 mg/mL logp -1.41 ALOGPS logs -2.48 ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 8.18 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one ChemAxon average_mass 237.2153 ChemAxon mono_mass 237.086189243 ChemAxon smiles C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1 ChemAxon formula C9H11N5O3 ChemAxon inchi InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1 ChemAxon inchikey LHQIJBMDNUYRAM-DZSWIPIPSA-N ChemAxon polar_surface_area 132.66 ChemAxon refractivity 57.81 ChemAxon polarizability 22.47 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge 0 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 Specdb::CMs 555 Specdb::CMs 22218 Specdb::CMs 30489 Specdb::CMs 37552 Specdb::CMs 149609 Specdb::CMs 1063089 Specdb::CMs 1063091 Specdb::CMs 1063093 Specdb::CMs 1063095 Specdb::CMs 1063097 Specdb::CMs 1063099 Specdb::CMs 1063101 Specdb::CMs 1063103 Specdb::CMs 1063105 Specdb::CMs 1063107 Specdb::CMs 1063109 Specdb::CMs 1063111 Specdb::CMs 1063112 Specdb::CMs 1063114 Specdb::CMs 1063117 Specdb::CMs 1063118 Specdb::CMs 1063120 Specdb::CMs 1063122 Specdb::CMs 1063124 Specdb::CMs 1063126 Specdb::NmrOneD 1383 Specdb::NmrOneD 144090 Specdb::NmrOneD 144091 Specdb::NmrOneD 144092 Specdb::NmrOneD 144093 Specdb::NmrOneD 144094 Specdb::NmrOneD 144095 Specdb::NmrOneD 144096 Specdb::NmrOneD 144097 Specdb::NmrOneD 144098 Specdb::NmrOneD 144099 Specdb::NmrOneD 144100 Specdb::NmrOneD 144101 Specdb::NmrOneD 144102 Specdb::NmrOneD 144103 Specdb::NmrOneD 144104 Specdb::NmrOneD 144105 Specdb::NmrOneD 144106 Specdb::NmrOneD 144107 Specdb::NmrOneD 144108 Specdb::NmrOneD 144109 Specdb::NmrOneD 166334 Specdb::NmrOneD 166673 Specdb::MsMs 680 Specdb::MsMs 681 Specdb::MsMs 682 Specdb::MsMs 315337 Specdb::MsMs 315338 Specdb::MsMs 315339 Specdb::MsMs 361279 Specdb::MsMs 361280 Specdb::MsMs 361281 Specdb::MsMs 2236580 Specdb::MsMs 2236813 Specdb::MsMs 2238711 Specdb::MsMs 2238865 Specdb::MsMs 2240839 Specdb::MsMs 2240869 Specdb::MsMs 2242872 Specdb::MsMs 2242960 Specdb::MsMs 2249081 Specdb::MsMs 2249292 Specdb::MsMs 2256696 Specdb::MsMs 2257881 Specdb::MsMs 2258666 Specdb::MsMs 2259916 Specdb::MsMs 2349502 Specdb::MsMs 2349503 Specdb::NmrTwoD 1327 Brain 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 Epidermis 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 Fibroblasts 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 Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 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 C06313 392795 FDB022060 445040 C00018229 63931 CPD-10819 Biopterin 247 Mori, Kenji; Kikuchi, Haruhiko. Synthesis of (-)-biopterin. Liebigs Annalen der Chemie (1989), (10), 963-7.