2.02012-05-31 13:56:27 -06002015-09-13 12:56:12 -0600ECMDB02275M2MDB0004547,8-Dihydroneopterin7,8-dihydroneopterin (H(2)Neo) is an intermediate in folate biosynthesis pathway. It is converted to glycolaldehyde and 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine via bifunctional dihydroneopterin aldolase/dihydroneopterin triphosphate 2'-epimerase (EC:4.1.2.25). it is also a substrate of alkaline phosphatase. (KEGG) Dihydromonapterin is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Dihydromonapterin is an intermediate in the synthesis of tetrahydromonopterin. Tetrahydromonapterin is the major tetrahydropterin in E. coli, although the biological role of tetrahydromonapterin in E. coli is currently unknown.2-Amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin2-Amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridine2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(1H)-one2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(3H)-one2-Amino-7,8-dihydro-6-(1,2,3-trihydroxypropyl)-4(1H)-pteridinone7,8-Dihydro-D-erythro-neopterin7,8-Dihydro-D-neopterin7,8-DihydroneopterinD-Erythro-7,8-DihydroneopterinDHMDHNDihydro-neo-pterinDihydroneopterinH2-MPtNPRC9H13N5O4255.2306255.0967539292-amino-6-(1,2,3-trihydroxypropyl)-1,4,7,8-tetrahydropteridin-4-one2-amino-6-(1,2,3-trihydroxypropyl)-7,8-dihydro-1H-pteridin-4-one1218-98-0NC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)CO)N1InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)YQIFAMYNGGOTFB-UHFFFAOYSA-NSolidCytosollogp-1.59logs-2.35solubility1.15e+00 g/llogp-3.3pka_strongest_acidic9.37pka_strongest_basic0.28iupac2-amino-6-(1,2,3-trihydroxypropyl)-1,4,7,8-tetrahydropteridin-4-oneaverage_mass255.2306mono_mass255.096753929smilesNC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)CO)N1formulaC9H13N5O4inchiInChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)inchikeyYQIFAMYNGGOTFB-UHFFFAOYSA-Npolar_surface_area152.56refractivity69.66polarizability23.99rotatable_bond_count3acceptor_count9donor_count6physiological_charge0formal_charge0Folate biosynthesisThe biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate.
This product goes on to a one carbon pool by folate pathway.
PW000908ec00790MetabolicMetabolic pathwayseco01100GTP degradationGTP, produced in the nucleotide de novo biosyntheis pathway, interacts with a water molecule through a GTP cyclohydrolase resulting in a formate, hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound interacts with a water molecule through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, a hydrogen ion and a 7,8-dihydroneopterin 3'-phosphate. The latter compound interacts with water spontaneously resulting in the release of a phosphate and a 7,8 dihydroneopterin. The latter compound interacts with a dihydroneopterin aldolase resulting in the release of a glycolaldehyde and a 6-hydroxymethyl-7,8-dihydropterin. This compound then is then diphosphorylated by reacting with a ATP driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in the release of a hydrogen ion, an AMP and 6-hydroxymethyl-7,8-dihydropterin diphosphate.
GTP interacts with a cyclic pyranopterin monophosphate synthase resulting in the release of a diphosphate and a cyclic pyranopterin phosphate. The latter compound interacts with a thiocarboxylated small subunit of molybdopterin synthase (a protein) and a water molecule through a molybdopterin synthase resulting in the release of 4 hydrogen ions, 2 small subunits of molybdopterin synthase and a molybdopterin. The molybdopterin interacts with an ATP and a hydrogen ion through a molybdopterin adenylyltransferase resulting in the release of a diphosphate and a molybdopterin adenine dinucleotide.PW001888Metabolic6-hydroxymethyl-dihydropterin diphosphate biosynthesis IPWY-6147tetrahydromonapterin biosynthesisPWY0-1433Specdb::CMs9654Specdb::CMs38349Specdb::CMs118517Specdb::CMs122055Specdb::CMs809960Specdb::CMs809961Specdb::CMs809962Specdb::CMs809963Specdb::NmrOneD171021Specdb::NmrOneD171022Specdb::NmrOneD171023Specdb::NmrOneD171024Specdb::NmrOneD171025Specdb::NmrOneD171026Specdb::NmrOneD171027Specdb::NmrOneD171028Specdb::NmrOneD171029Specdb::NmrOneD171030Specdb::NmrOneD171031Specdb::NmrOneD171032Specdb::NmrOneD171033Specdb::NmrOneD171034Specdb::NmrOneD171035Specdb::NmrOneD171036Specdb::NmrOneD171037Specdb::NmrOneD171038Specdb::NmrOneD171039Specdb::NmrOneD171040Specdb::MsMs26318Specdb::MsMs26319Specdb::MsMs26320Specdb::MsMs32876Specdb::MsMs32877Specdb::MsMs32878Specdb::MsMs1475734Specdb::MsMs1475735Specdb::MsMs1475736Specdb::MsMs1475737Specdb::MsMs1475738Specdb::MsMs1475739Specdb::MsMs1475740Specdb::MsMs1475741Specdb::MsMs1475742Specdb::MsMs1475743Specdb::MsMs1475744Specdb::MsMs1475745Specdb::MsMs1475746Specdb::MsMs1475747Specdb::MsMs1475748Specdb::MsMs1475749Specdb::MsMs1475750Specdb::MsMs1475751Specdb::MsMs1475752HMDB02275659639C0487417001DIHYDRO-NEO-PTERINKeseler, I. 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Free Radic Res. 2001 Sep;35(3):311-8.11697129http://hmdb.ca/system/metabolites/msds/000/001/858/original/HMDB02275.pdf?1358462838Alkaline phosphataseP00634PPB_ECOLIphoAhttp://ecmdb.ca/proteins/P00634.xmlDihydroneopterin aldolaseP0AC16FOLB_ECOLIfolBhttp://ecmdb.ca/proteins/P0AC16.xmlDihydrofolate reductase folMP0AFS3FOLM_ECOLIfolMhttp://ecmdb.ca/proteins/P0AFS3.xml7,8-Dihydroneopterin + Hydrogen ion + NADPH > NADP + TetrahydromonapterinRXN0-63677,8-Dihydroneopterin <> 6-Hydroxymethyl dihydropterin + GlycolaldehydeR03504H2NEOPTERINALDOL-RXN7,8-Dihydroneopterin <> 7,8-DihydroneopterinRXN-108567,8-Dihydroneopterin <> 7,8-DihydroneopterinRXN-10856Dihydroneopterin triphosphate + 3 Water <> 7,8-Dihydroneopterin +3 PhosphateR04620Dihydromonapterin-triphosphate + Water > Hydrogen ion + 7,8-Dihydroneopterin + PhosphateRXN0-6368Dihydroneopterin monophosphate + Water > 7,8-Dihydroneopterin + PhosphateDIHYDRONEOPTERIN-MONO-P-DEPHOS-RXN7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterinH2NEOPTERINALDOL-RXNTetrahydromonapterin + NADP < Hydrogen ion + 7,8-Dihydroneopterin + NADPHRXN0-63677,8-Dihydroneopterin + 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterinPW_R0033997 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + GlycolaldehydeDihydroneopterin triphosphate + 3 Water <>7 7,8-Dihydroneopterin +3 Phosphate7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde