1.0 2011-09-21 00:14:54 UTC 2015-07-21 06:57:14 UTC FDB022495 Tetrahydropteridine Tetrahydrobiopterin serves well-characterized cofactor functions for hydroxylating aromatic amino acids and ether lipids and for formation of nitric oxide (NO) from L-arginine. Formation of NO involves two cycles of oxidation of Tetrahydrobiopterin to its radical with subsequent rehydroxylation into Tetrahydrobiopterin, one for reduction of the heme-bound arginine-Fe(II)O2 complex of NO synthase (NOS), the other for reduction of the N-hydroxy-L-arginine-Fe(II)O2 complex. Tetrahydrobiopterin-dependent glyceryl ether monooxygenase (EC 1.14.16.5) is found not only in liver and the gastrointestinal tract but also in brain and other organs (this enzyme plays an essential role in conjugation with the cleavage enzyme in the regulation of cellular levels of -alkyl moieties in glycerolipids). Tetrahydrobiopterin is essential for the enzymatic reaction of tyrosine 3-monooxygenase (EC 1.14.16.2) for the first step in the biosynthesis of catecholamines such as norepinephrine, epinephrine and dopamine. Limited Tetrahydrobiopterin availability not only decreases formation of NO but also causes NOS-derived superoxide/hydrogen peroxide production leading to formation of peroxynitrite as well as S-nitrosoglutathione. As a consequence of its oxygen-activating potential, Tetrahydrobiopterin is also subject to autoxidation in a free radical chain reaction in leading to formation of superoxide and finally to hydrogen peroxide. On the other hand, Tetrahydrobiopterin, like other H4-pterins, can scavenge reactive oxygen species and peroxynitrite. Thus, Tetrahydrobiopterin may have opposing effects in various biological systems depending on whether its cofactor roles outweigh its chemical reactivity or vice versa. Sepiapterin reductase (EC 1.1.1.153) catalyzes the reduction of tetrahydro-sepiapterin to tetrahydrobiopterin -the terminal step in this biosynthetic pathway for tetrahydrobiopterin. This reaction is N-acetyl-serotonin-sensitive and can completely inhibit tetrahydrobiopterin synthesis. (PMID: 3881214, 17303893, 3756924, 15223071) [HMDB] 5,6,7,8-tetrahydro-Pteridine 5,6,7,8-Tetrahydropteridine H4-biopterin THP C6H8N4 136.1545 136.074896276 5,6,7,8-tetrahydropteridine 5,6,7,8-tetrahydropteridine 10593-78-9 C1CNC2=C(N1)C=NC=N2 InChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10) IDAICLIJTRXNER-UHFFFAOYSA-N belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. Pteridines and derivatives Organic compounds Organoheterocyclic compounds Pteridines and derivatives Aromatic heteropolycyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Organopnictogen compounds Pyrimidines and pyrimidine derivatives Secondary alkylarylamines Amine Aromatic heteropolycyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Imidolactam Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pteridine Pyrimidine Secondary aliphatic/aromatic amine Secondary amine a small molecule pteridines Solid logp 0.29 ALOGPS logs -1.98 ALOGPS solubility 1.43e+00 g/l ALOGPS logp -0.58 ChemAxon pka_strongest_acidic 19.35 ChemAxon pka_strongest_basic 5.42 ChemAxon iupac 5,6,7,8-tetrahydropteridine ChemAxon average_mass 136.1545 ChemAxon mono_mass 136.074896276 ChemAxon smiles C1CNC2=C(N1)C=NC=N2 ChemAxon formula C6H8N4 ChemAxon inchi InChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10) ChemAxon inchikey IDAICLIJTRXNER-UHFFFAOYSA-N ChemAxon polar_surface_area 49.84 ChemAxon refractivity 41.45 ChemAxon polarizability 13.53 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16404 Specdb::CMs 153901 Specdb::MsIr 1136 Specdb::MsIr 1137 Specdb::MsIr 1138 Specdb::MsMs 28694 Specdb::MsMs 28695 Specdb::MsMs 28696 Specdb::MsMs 35252 Specdb::MsMs 35253 Specdb::MsMs 35254 Specdb::MsMs 2785786 Specdb::MsMs 2785787 Specdb::MsMs 2785788 Specdb::MsMs 2922646 Specdb::MsMs 2922647 Specdb::MsMs 2922648 Specdb::NmrOneD 87572 Specdb::NmrOneD 87573 Specdb::NmrOneD 87574 Specdb::NmrOneD 87575 Specdb::NmrOneD 87576 Specdb::NmrOneD 87577 Specdb::NmrOneD 87578 Specdb::NmrOneD 87579 Specdb::NmrOneD 87580 Specdb::NmrOneD 87581 Specdb::NmrOneD 87582 Specdb::NmrOneD 87583 Specdb::NmrOneD 87584 Specdb::NmrOneD 87585 Specdb::NmrOneD 87586 Specdb::NmrOneD 87587 Specdb::NmrOneD 87588 Specdb::NmrOneD 87589 Specdb::NmrOneD 87590 Specdb::NmrOneD 87591 HMDB01216 28889 #<Reference:0x000055ce32cdaa68> #<Reference:0x000055ce32cda7e8> #<Reference:0x000055ce32cda590> #<Reference:0x000055ce32cda2e8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823