1.0 2016-09-30 22:18:39 UTC 2020-05-21 16:29:04 UTC BMDB0000027 BMDB0000787 BMDB00027 BMDB00787 Tetrahydrobiopterin (-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone (6R)-L-Erythro-5,6,7,8-tetrahydrobiopterin (6R)-L-Erythro-tetrahydrobiopterin 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone 5,6,7,8-Tetrahydrobiopterin 6R-5,6,7,8-Tetrahydrobiopterin 6R-BH4 6R-L-5,6,7,8-Tetrahydrobiopterin R-THBP Sapropterina Sapropterinum Tetrahydrobiopterin 5,6,7,8-erythro-Tetrahydrobiopterin 5,6,7,8-tetrahydro-L-Erythrobiopterin 5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomer 5,6,7,8-Tetrahydrodictyopterin 6R-L-erythro-5,6,7,8-Tetrahydrobiopterin BPH4 D-threo-Tetrahydrobiopterin THBP Kuvan Phenylalanine hydroxylase cofactor Sapropterin dihydrochloride tetrahydro-6-Biopterin 2',4',5'-Trihydroxybutyrophenone Sapropterin Trihydroxybutyrophenone 1-Butanone, 1-(2,4,5-trihydroxyphenyl) 2,4,5-Trihydroxybutyrophenone (6R)-5,6,7,8-Tetrahydro-L-biopterin (6R)-5,6,7,8-Tetrahydrobiopterin (6R)-Tetrahydrobiopterin 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone 6R-Tetrahydro-L-biopterin 6beta-5,6,7,8-Tetrahydro-L-biopterin 6β-5,6,7,8-Tetrahydro-L-biopterin L-erythro-Tetrahydrobiopterin (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone C9H15N5O3 241.2471 241.117489371 (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one tetrahydrobiopterin 27070-47-9 [H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1 FNKQXYHWGSIFBK-RPDRRWSUSA-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-aminoalcohols 1,2-diols 1,3-aminoalcohols Aminopyrimidines and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines Pyrimidones Secondary alcohols Secondary alkylarylamines Vinylogous amides 1,2-aminoalcohol 1,2-diol 1,3-aminoalcohol Alcohol Amine Aminopyrimidine 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 Pyrimidine Pyrimidone Secondary alcohol Secondary aliphatic/aromatic amine Secondary amine Vinylogous amide Aromatic heteropolycyclic compounds 5,6,7,8-tetrahydrobiopterin Coenzymes Solid melting_point 250 - 255 °C (hydrochloride salt) logp -1.66 ALOGPS logs -2.04 ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 13.52 ChemAxon pka_strongest_basic 1.58 ChemAxon iupac (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one ChemAxon average_mass 241.2471 ChemAxon mono_mass 241.117489371 ChemAxon smiles [H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O ChemAxon formula C9H15N5O3 ChemAxon inchi InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1 ChemAxon inchikey FNKQXYHWGSIFBK-RPDRRWSUSA-N ChemAxon polar_surface_area 132 ChemAxon refractivity 68.43 ChemAxon polarizability 23.67 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 6 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 Arginine and Proline Metabolism SMP0087178 Ion Channels and Their Functional Role in Vascular Endothelium SMP0108207 Pterine Biosynthesis SMP0087250 Tryptophan Metabolism SMP0087237 Tyrosine Metabolism SMP0087235 Specdb::NmrOneD 299625 Specdb::NmrOneD 299626 Specdb::NmrOneD 299627 Specdb::NmrOneD 299628 Specdb::NmrOneD 299629 Specdb::NmrOneD 299630 Specdb::NmrOneD 299631 Specdb::NmrOneD 299632 Specdb::NmrOneD 299633 Specdb::NmrOneD 299634 Specdb::NmrOneD 299635 Specdb::NmrOneD 299636 Specdb::NmrOneD 299637 Specdb::NmrOneD 299638 Specdb::NmrOneD 299639 Specdb::NmrOneD 299640 Specdb::NmrOneD 299641 Specdb::NmrOneD 299642 Specdb::NmrOneD 299643 Specdb::NmrOneD 299644 Specdb::MsMs 25520 Specdb::MsMs 25521 Specdb::MsMs 25522 Specdb::MsMs 32078 Specdb::MsMs 32079 Specdb::MsMs 32080 Specdb::MsMs 1473642 Specdb::MsMs 1473643 Specdb::MsMs 1473644 Specdb::MsMs 1473645 Specdb::MsMs 1473646 Specdb::MsMs 1473647 Specdb::MsMs 1473648 Specdb::MsMs 1474434 Specdb::MsMs 1474435 Specdb::MsMs 1474436 Specdb::MsMs 1474437 Specdb::MsMs 1474438 Specdb::MsMs 1475535 Specdb::MsMs 1475536 Specdb::MsMs 1475537 Specdb::MsMs 1475538 Specdb::MsMs 1475539 Specdb::MsMs 1475540 Specdb::MsMs 1477738 Specdb::CMs 1999 Specdb::CMs 31663 Specdb::CMs 35145 Specdb::CMs 47846 Specdb::CMs 159887 Specdb::CMs 1047073 Specdb::CMs 1047075 Specdb::CMs 1047077 Specdb::CMs 1047079 Specdb::CMs 1047081 Specdb::CMs 1047082 Specdb::CMs 1047084 Specdb::CMs 1047086 Specdb::CMs 1047087 Specdb::CMs 1047088 Specdb::CMs 1047089 Specdb::CMs 1047090 Specdb::CMs 1047091 Specdb::CMs 1047093 Specdb::CMs 1047095 Specdb::CMs 1047097 Specdb::CMs 1047099 Specdb::CMs 1047100 Specdb::CMs 1047102 Specdb::CMs 1047104 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 40270 C00272 DB00360 44257 59560 CPD-14053 Sapropterin Steven S. Gross, "Blocking utilization of tetrahydrobiopterin to block induction of nitric oxide synthesis." U.S. Patent US5502050, issued October, 1984. BMDBP00022 Nitric oxide synthase, endothelial P29473 NOS3 Enzyme BMDBP00069 Nitric oxide synthase, inducible Q27995 NOS2 Enzyme BMDBP00379 Sepiapterin reductase Q17QK8 SPR Enzyme BMDBP00388 Tyrosine 3-monooxygenase P17289 TH Enzyme BMDBP00389 Phenylalanine-4-hydroxylase Q2KIH7 PAH Enzyme BMDBP00557 Inducible nitric oxid synthase Q6ZXD5 iNOS Enzyme BMDBP00597 Dihydropteridine reductase Q3T0Z7 QDPR Enzyme BMDBP00821 Dihydrofolate reductase P00376 DHFR Enzyme