1.0 2011-09-21 00:20:14 UTC 2015-07-21 06:57:23 UTC FDB022828 6-Lactoyltetrahydropterin 6-Lactoyltetrahydropterin is a putative intermediate in the de novo synthesis of tetrahydrobiopterin (BH4) pathway, in a reaction involving the enzyme sepiapterin reductase (E.C. 1.1.1.153) in human liver. In brain, an enzyme distinct from sepiapterin reductase catalyzes the TPNH-dependent reduction of 6-pyruvoyl-tetrahydropterin to 6-lactoyl-tetrahydropterin. (PMID: 4004850) In brain, the expression of other enzymes involved in BH4 biosynthesis includes aldose reductase, carbonyl reductase, GTP-cyclohydrolase I, and 6-pyruvoyltetrahydrobiopterin. Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. (PMID: 17270157) [HMDB] 2-amino-6-Lactoyl-5,6,7,8-tetrahydropteridin-4(3H)-one 6-1'-oxo-2'-Hydroxypropyl tetrahydropterin 6-Lactoyl tetrahydropterin 6-lactoyl-5,6,7,8-tetrahydropterin Lactoyl-H4-pterin Lactoyl-PH4 C9H13N5O3 239.2312 239.101839307 2-amino-6-(2-hydroxypropanoyl)-3,4,5,6,7,8-hexahydropteridin-4-one 6-lactoyl tetrahydropterin 33405-80-0 CC(O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2 InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,12,15H,2H2,1H3,(H4,10,11,13,14,17) HKCYZTKHPLJZDR-UHFFFAOYSA-N belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. Pterins and derivatives Organic compounds Organoheterocyclic compounds Pteridines and derivatives Pterins and derivatives Aromatic heteropolycyclic compounds 1,3-aminoalcohols Acyloins Alpha-amino ketones Alpha-hydroxy ketones Aminopyrimidines and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines Pyrimidones Secondary alcohols Secondary alkylarylamines Vinylogous amides 1,3-aminoalcohol Acyloin Alcohol Alpha-aminoketone Alpha-hydroxy ketone Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Carbonyl group Heteroaromatic compound Hydrocarbon derivative Ketone Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Pterin Pyrimidine Pyrimidone Secondary alcohol Secondary aliphatic/aromatic amine Secondary amine Vinylogous amide a small molecule tetrahydropterin Solid logp -1.55 ALOGPS logs -2.29 ALOGPS solubility 1.21e+00 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 11.12 ChemAxon pka_strongest_basic 4.62 ChemAxon iupac 2-amino-6-(2-hydroxypropanoyl)-3,4,5,6,7,8-hexahydropteridin-4-one ChemAxon average_mass 239.2312 ChemAxon mono_mass 239.101839307 ChemAxon smiles CC(O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2 ChemAxon formula C9H13N5O3 ChemAxon inchi InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,12,15H,2H2,1H3,(H4,10,11,13,14,17) ChemAxon inchikey HKCYZTKHPLJZDR-UHFFFAOYSA-N ChemAxon polar_surface_area 128.84 ChemAxon refractivity 67.87 ChemAxon polarizability 22.59 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pterine Biosynthesis SMP00005 map00790 Specdb::CMs 22301 Specdb::CMs 38252 Specdb::CMs 128509 Specdb::CMs 146450 Specdb::CMs 972220 Specdb::CMs 972221 Specdb::CMs 972222 Specdb::CMs 972223 Specdb::CMs 972224 Specdb::CMs 972225 Specdb::CMs 972226 Specdb::CMs 972227 Specdb::CMs 972228 Specdb::CMs 972229 Specdb::CMs 972230 Specdb::CMs 972231 Specdb::CMs 972232 Specdb::MsMs 315508 Specdb::MsMs 315509 Specdb::MsMs 315510 Specdb::MsMs 361513 Specdb::MsMs 361514 Specdb::MsMs 361515 Specdb::MsMs 2366923 Specdb::MsMs 2366924 Specdb::MsMs 2366925 Specdb::MsMs 2598223 Specdb::MsMs 2598224 Specdb::MsMs 2598225 Specdb::NmrOneD 10062 Specdb::NmrOneD 10063 Specdb::NmrOneD 10064 Specdb::NmrOneD 10065 Specdb::NmrOneD 10066 Specdb::NmrOneD 10067 Specdb::NmrOneD 10068 Specdb::NmrOneD 10069 Specdb::NmrOneD 10070 Specdb::NmrOneD 10071 Specdb::NmrOneD 10072 Specdb::NmrOneD 10073 Specdb::NmrOneD 10074 Specdb::NmrOneD 10075 Specdb::NmrOneD 10076 Specdb::NmrOneD 10077 Specdb::NmrOneD 10078 Specdb::NmrOneD 10079 Specdb::NmrOneD 10080 Specdb::NmrOneD 10081 HMDB02065 17248 #<Reference:0x000055ce335dfb18> #<Reference:0x000055ce335df960> 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 Sepiapterin reductase P35270 SPR