2.0 2015-07-14 14:32:01 -0600 2015-07-23 12:07:42 -0600 ECMDB23994 M2MDB006115 THF-polyglutamate (6S)-H4PteGlu(N) Tetrahydrofolyl-[glu](N) Tetrahydrofolyl-[glu](N-1) Tetrahydropteroyl-[g-glu]N Tetrahydropteroyl-[g-glu]n+1 Tetrahydropteroyl-[gamma-glu]N Tetrahydropteroyl-[gamma-glu]n+1 Tetrahydropteroyl-[γ-glu]N Tetrahydropteroyl-[γ-glu]n+1 THF-Polyglutamic acid C29H37N9O12 703.6572 703.256167693 (2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid (2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1 InChI=1S/C29H37N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)/t15-,16-,17-,18-/m0/s1 RXWVHRYZTWZATH-XSLAGTTESA-N logp -1.64 ALOGPS logs -3.29 ALOGPS solubility 3.59e-01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 2.59 ChemAxon pka_strongest_basic 3.12 ChemAxon iupac (2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid ChemAxon average_mass 703.6572 ChemAxon mono_mass 703.256167693 ChemAxon smiles NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1 ChemAxon formula C29H37N9O12 ChemAxon inchi InChI=1S/C29H37N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)/t15-,16-,17-,18-/m0/s1 ChemAxon inchikey RXWVHRYZTWZATH-XSLAGTTESA-N ChemAxon polar_surface_area 340.07 ChemAxon refractivity 177.56 ChemAxon polarizability 69.1 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 18 ChemAxon donor_count 12 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The 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. PW000908 ec00790 Metabolic Metabolic pathways eco01100 Specdb::CMs 59522 Specdb::CMs 749755 Specdb::CMs 749756 Specdb::CMs 749757 Specdb::CMs 749758 Specdb::CMs 749759 Specdb::CMs 749760 Specdb::CMs 749761 Specdb::CMs 749762 Specdb::CMs 749763 Specdb::CMs 749764 Specdb::CMs 749765 Specdb::CMs 749766 Specdb::CMs 749767 Specdb::CMs 749768 Specdb::CMs 749769 Specdb::CMs 749770 Specdb::CMs 749771 Specdb::CMs 749772 Specdb::CMs 749773 Specdb::CMs 749774 Specdb::CMs 749775 Specdb::CMs 749776 Specdb::CMs 749777 Specdb::CMs 749778 Specdb::NmrOneD 97058 Specdb::NmrOneD 97059 Specdb::NmrOneD 97060 Specdb::NmrOneD 97061 Specdb::NmrOneD 97062 Specdb::NmrOneD 97063 Specdb::NmrOneD 97064 Specdb::NmrOneD 97065 Specdb::NmrOneD 97066 Specdb::NmrOneD 97067 Specdb::NmrOneD 97068 Specdb::NmrOneD 97069 Specdb::NmrOneD 97070 Specdb::NmrOneD 97071 Specdb::NmrOneD 97072 Specdb::NmrOneD 97073 Specdb::NmrOneD 97074 Specdb::NmrOneD 97075 Specdb::NmrOneD 97076 Specdb::NmrOneD 97077 Specdb::MsMs 38606 Specdb::MsMs 38607 Specdb::MsMs 38608 Specdb::MsMs 41054 Specdb::MsMs 41055 Specdb::MsMs 41056 Specdb::MsMs 2791913 Specdb::MsMs 2791914 Specdb::MsMs 2791915 Specdb::MsMs 2916908 Specdb::MsMs 2916909 Specdb::MsMs 2916910 C03541 Adenosine triphosphate + THF-polyglutamate + L-Glutamate <> ADP + Phosphate R04241