2.0 2012-05-31 13:45:58 -0600 2015-06-03 15:53:46 -0600 ECMDB01131 M2MDB000267 Iminoaspartic acid Iminoaspartic acid (alpha-iminosuccinate) is an intermediate in NAD biosynthesis from aspartate pathwyay. As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate, while in eukaryotes, the de novo pathway starts with tryptophan. a-Iminosuccinate a-Iminosuccinic acid Alpha-Iminosuccinate Alpha-Iminosuccinic acid Imino-Butanedioate Imino-Butanedioic acid Iminoaspartate Iminoaspartic acid Iminosuccinate Iminosuccinic acid α-Iminosuccinate α-Iminosuccinic acid C4H5NO4 131.0868 131.021857653 2-iminobutanedioic acid iminosuccinic acid 79067-61-1 OC(=O)CC(=N)C(O)=O InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9) NMUOATVLLQEYHI-UHFFFAOYSA-N Solid Cytosol logp -0.83 ALOGPS logs -1.49 ALOGPS solubility 4.26e+00 g/l ALOGPS logp -0.51 ChemAxon pka_strongest_acidic 3.28 ChemAxon pka_strongest_basic 2.48 ChemAxon iupac 2-iminobutanedioic acid ChemAxon average_mass 131.0868 ChemAxon mono_mass 131.021857653 ChemAxon smiles OC(=O)CC(=N)C(O)=O ChemAxon formula C4H5NO4 ChemAxon inchi InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9) ChemAxon inchikey NMUOATVLLQEYHI-UHFFFAOYSA-N ChemAxon polar_surface_area 98.45 ChemAxon refractivity 36.81 ChemAxon polarizability 10.55 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Alanine, aspartate and glutamate metabolism ec00250 Nicotinate and nicotinamide metabolism ec00760 Metabolic pathways eco01100 NAD biosynthesis Nicotinamide adenine dinucleotide (NAD) can be biosynthesized from L-aspartic acid.This amino acid reacts with oxygen through an L-aspartate oxidase resulting in a hydrogen ion, hydrogen peroxide and an iminoaspartic acid. The latter compound interacts with dihydroxyacetone phosphate through a quinolinate synthase A, resulting in a phosphate, water, and a quinolic acid. Quinolic acid interacts with phosphoribosyl pyrophosphate and hydrogen ion through a quinolinate phosphoribosyltransferase resulting in pyrophosphate, carbon dioxide and nicotinate beta-D-ribonucleotide. This last compound is adenylated through an ATP driven nicotinate-mononucleotide adenylyltransferase releasing a pyrophosphate and resulting in a nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide is processed through an NAD synthetase, NH3-dependent in two different manners. In the first case, Nicotinic acid adenine dinucleotide interacts with ATP, L-glutamine and water through the enzyme and results in hydrogen ion, AMP, pyrophosphate, L-glutamic acid and NAD. In the second case, Nicotinic acid adenine dinucleotide interacts with ATP and ammonium through the enzyme resulting in a pyrophosphate, AMP, hydrogen ion and NAD. NAD then proceeds to regulate its own pathway by repressing L-aspartate oxidase. As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate , while in eukaryotes, the de novo pathway starts with tryptophan. PW000829 Metabolic NAD biosynthesis I (from aspartate) PYRIDNUCSYN-PWY Specdb::CMs 3108 Specdb::CMs 37940 Specdb::CMs 132222 Specdb::CMs 139956 Specdb::NmrOneD 259728 Specdb::NmrOneD 259729 Specdb::NmrOneD 259730 Specdb::NmrOneD 259731 Specdb::NmrOneD 259732 Specdb::NmrOneD 259733 Specdb::NmrOneD 259734 Specdb::NmrOneD 259735 Specdb::NmrOneD 259736 Specdb::NmrOneD 259737 Specdb::NmrOneD 259738 Specdb::NmrOneD 259739 Specdb::NmrOneD 259740 Specdb::NmrOneD 259741 Specdb::NmrOneD 259742 Specdb::NmrOneD 259743 Specdb::NmrOneD 259744 Specdb::NmrOneD 259745 Specdb::NmrOneD 259746 Specdb::NmrOneD 259747 Specdb::MsMs 28265 Specdb::MsMs 28266 Specdb::MsMs 28267 Specdb::MsMs 34823 Specdb::MsMs 34824 Specdb::MsMs 34825 Specdb::MsMs 2746079 Specdb::MsMs 2746080 Specdb::MsMs 2746081 Specdb::MsMs 2936776 Specdb::MsMs 2936777 Specdb::MsMs 2936778 HMDB01131 796 13628208 C05840 IMINOASPARTATE Keseler, I. 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"Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 L-aspartate oxidase P10902 NADB_ECOLI nadB http://ecmdb.ca/proteins/P10902.xml Quinolinate synthase A P11458 NADA_ECOLI nadA http://ecmdb.ca/proteins/P11458.xml Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid R04292 QUINOLINATE-SYNTHA-RXN L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid RXN-9772 L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid R00481 L-ASPARTATE-OXID-RXN L-Aspartic acid + Ubiquinone-8 > Hydrogen ion + Iminoaspartic acid + Ubiquinol-8 L-Aspartic acid + Menaquinone 8 > Hydrogen ion + Iminoaspartic acid + Menaquinol 8 L-Aspartic acid + Oxygen <> Iminoaspartic acid + Hydrogen peroxide R00481 L-ASPARTATE-OXID-RXN Quinolinic acid + 2 Water + Phosphate <> Iminoaspartic acid + Dihydroxyacetone phosphate R04292 Oxygen + L-Aspartic acid > Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid L-ASPARTATE-OXID-RXN Iminoaspartic acid + Dihydroxyacetone phosphate > Quinolinic acid + Water + Phosphate QUINOLINATE-SYNTHA-RXN Dihydroxyacetone phosphate + Iminoaspartic acid > Quinolinic acid +2 Water + Inorganic phosphate L-Aspartic acid + Oxygen > Iminoaspartic acid + Hydrogen peroxide L-Aspartic acid + Oxygen + L-Aspartic acid > Hydrogen peroxide + Hydrogen ion + Iminoaspartic acid PW_R003007 Iminoaspartic acid + Dihydroxyacetone phosphate > Phosphate +2 Water + Quinolinic acid PW_R003008 L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid Quinolinic acid + 2 Water + Phosphate <> Iminoaspartic acid + Dihydroxyacetone phosphate L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid