1.0 2011-09-21 01:45:09 UTC 2018-05-29 01:54:38 UTC FDB028801 2-Amino-4-oxo-6-(1',2',3'-trihydroxypropyl)-diquinoid-7,8-dihydroxypterin 2-Amino-4-oxo-6-(1',2',3'-trihydroxypropyl)-diquinoid-7,8-dihydroxypterin is a pterin derivative. Pterin is a heterocyclic compound composed of a pyrazine ring and a pyrimidine ring with Several tautomers; the pyrimidine ring has a carbonyl oxygen and an amino group. As a group, pterins are compounds that are derivatives of 2-amino-4-oxopteridine, with additional functional groups attached to the pyrazine ring. Pterins were first discovered in the pigments of butterfly wings and perform many roles in coloration in the biological world. Pterins also function as cofactors in enzyme catalysis . Some pterin derivatives (biopterin, 6-formylpterin, 6-carboxypterin) accumulate in the skin of patients affected by vitiligo, a depigmentation disorder, where the protection against UV radiation fails due to the lack of melanin. Pterins participate in biologically important photosensitization processes; for example, pterins act as sensitizers in photochemical reactions that induce DNA damage4,5 and are able to generate singlet molecular oxygen6 and other reactive oxygen species (PMID: 19199487). [HMDB] C9H15N5O6 289.2453 289.102233237 2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,4,5,6,7,8-hexahydropteridin-4-one 2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,5,6,7-tetrahydropteridin-4-one NC1=NC2=C(NC(C(O)C(O)CO)C(O)N2O)C(=O)N1 InChI=1S/C9H15N5O6/c10-9-12-6-4(7(18)13-9)11-3(8(19)14(6)20)5(17)2(16)1-15/h2-3,5,8,11,15-17,19-20H,1H2,(H3,10,12,13,18) KQZRTOGFDRQBSR-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. Biopterins and derivatives Organic compounds Organoheterocyclic compounds Pteridines and derivatives Pterins and derivatives Aromatic heteropolycyclic compounds 1,2-aminoalcohols 1,3-aminoalcohols Aminopyrimidines and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives N-organohydroxylamines Organic oxides Organopnictogen compounds Polyols Primary alcohols Primary amines Pyrimidones Secondary alcohols Secondary alkylarylamines Vinylogous amides 1,2-aminoalcohol 1,3-aminoalcohol Alcohol Alkanolamine Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Biopterin Heteroaromatic compound Hydrocarbon derivative N-organohydroxylamine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Polyol Primary alcohol Primary amine Pyrimidine Pyrimidone Secondary alcohol Secondary aliphatic/aromatic amine Secondary amine Vinylogous amide Solid logp -2.44 ALOGPS logs -1.40 ALOGPS solubility 1.15e+01 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 11.06 ChemAxon pka_strongest_basic 3.68 ChemAxon iupac 2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,4,5,6,7,8-hexahydropteridin-4-one ChemAxon average_mass 289.2453 ChemAxon mono_mass 289.102233237 ChemAxon smiles NC1=NC2=C(NC(C(O)C(O)CO)C(O)N2O)C(=O)N1 ChemAxon formula C9H15N5O6 ChemAxon inchi InChI=1S/C9H15N5O6/c10-9-12-6-4(7(18)13-9)11-3(8(19)14(6)20)5(17)2(16)1-15/h2-3,5,8,11,15-17,19-20H,1H2,(H3,10,12,13,18) ChemAxon inchikey KQZRTOGFDRQBSR-UHFFFAOYSA-N ChemAxon polar_surface_area 183.9 ChemAxon refractivity 72.97 ChemAxon polarizability 26.02 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 10 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 25403 Specdb::CMs 39829 Specdb::CMs 147507 Specdb::MsMs 322246 Specdb::MsMs 322247 Specdb::MsMs 322248 Specdb::MsMs 370099 Specdb::MsMs 370100 Specdb::MsMs 370101 Specdb::MsMs 2335156 Specdb::MsMs 2335157 Specdb::MsMs 2335158 Specdb::MsMs 2626601 Specdb::MsMs 2626602 Specdb::MsMs 2626603 Specdb::NmrOneD 11422 Specdb::NmrOneD 11423 Specdb::NmrOneD 11424 Specdb::NmrOneD 11425 Specdb::NmrOneD 11426 Specdb::NmrOneD 11427 Specdb::NmrOneD 11428 Specdb::NmrOneD 11429 Specdb::NmrOneD 11430 Specdb::NmrOneD 11431 Specdb::NmrOneD 11432 Specdb::NmrOneD 11433 Specdb::NmrOneD 11434 Specdb::NmrOneD 11435 Specdb::NmrOneD 11436 Specdb::NmrOneD 11437 Specdb::NmrOneD 11438 Specdb::NmrOneD 11439 Specdb::NmrOneD 11440 Specdb::NmrOneD 11441 HMDB12144 #<Reference:0x000055ce3003dc08> 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