1.0 2016-09-30 22:53:33 UTC 2020-04-22 15:10:29 UTC BMDB0002281 BMDB02281 4a-Hydroxytetrahydrobiopterin 4a-Hydroxytetrahydrobiopterin, also known as 4a-hydroxytetrahydrobiopterin, 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. 4a-Hydroxytetrahydrobiopterin is possibly soluble (in water) and a strong basic compound (based on its pKa). Dopamine and 4a-hydroxytetrahydrobiopterin can be biosynthesized from L-dopa and tetrahydrobiopterin; which is catalyzed by the enzyme aromatic-L-amino-acid decarboxylase. In cattle, 4a-hydroxytetrahydrobiopterin is involved in the metabolic pathway called the tyrosine metabolism pathway. 4a-Hydroxy-5,6,4,8-tetrahydrobiopterin (6R)-6-(L-erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin 2-amino-6-(1,2-Dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4(4ah)-one 2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxy-4(4ah)-pteridinone 2-amino-6-[(1R,2S)-1,2-Dihydroxypropyl]-4a-hydroxy-1,5,6,7-tetrahydropteridin-4-one 4a-Hydroxy-5,6,7,8-tetrahydrobiopterin 4alpha-Hydroxytetrahydrobiopterin 4a-HTHB C9H15N5O4 257.2465 257.112403993 2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one 4a-hydroxytetrahydrobiopterin 70110-58-6 CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1 InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17) KJKIEFUPAPPGBC-UHFFFAOYSA-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 Alkanolamines Azacyclic compounds Carboxamidines Carboximidamides Dialkylamines Hydrocarbon derivatives Hydropyrimidines Imidolactams Imines Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Secondary alcohols 1,2,5,6-tetrahydropyrimidine 1,2-diol Alcohol Aliphatic heteropolycyclic compound Alkanolamine Amidine Amine Azacycle Biopterin Carboximidamide Carboxylic acid amidine Hydrocarbon derivative Hydropyrimidine Imidolactam Imine Organic 1,3-dipolar compound Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Secondary alcohol Secondary aliphatic amine Secondary amine Aliphatic heteropolycyclic compounds a small molecule tetrahydropterin Solid logp -2.29 ALOGPS logs -1.73 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 9.81 ChemAxon pka_strongest_basic 3.85 ChemAxon iupac 2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one ChemAxon average_mass 257.2465 ChemAxon mono_mass 257.112403993 ChemAxon smiles CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1 ChemAxon formula C9H15N5O4 ChemAxon inchi InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17) ChemAxon inchikey KJKIEFUPAPPGBC-UHFFFAOYSA-N ChemAxon polar_surface_area 152.56 ChemAxon refractivity 58.6 ChemAxon polarizability 24.2 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 9 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 Phenylalanine and Tyrosine Metabolism SMP0087218 Tryptophan Metabolism SMP0087237 Tyrosine Metabolism SMP0087235 Specdb::CMs 11568 Specdb::CMs 38353 Specdb::MsMs 291520 Specdb::MsMs 291521 Specdb::MsMs 291522 Specdb::MsMs 331453 Specdb::MsMs 331454 Specdb::MsMs 331455 Specdb::MsMs 3608167 Specdb::MsMs 3608168 Specdb::MsMs 3608169 Specdb::MsMs 3608170 Specdb::MsMs 3608171 Specdb::MsMs 3608172 FDB030533 114908 129803 15374 CPD-5881 BMDBP00388 Tyrosine 3-monooxygenase P17289 TH Enzyme BMDBP00389 Phenylalanine-4-hydroxylase Q2KIH7 PAH Enzyme