2.02012-05-31 13:45:58 -06002015-06-03 15:53:46 -0600ECMDB01131M2MDB000267Iminoaspartic acidIminoaspartic 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-Iminosuccinatea-Iminosuccinic acidAlpha-IminosuccinateAlpha-Iminosuccinic acidImino-ButanedioateImino-Butanedioic acidIminoaspartateIminoaspartic acidIminosuccinateIminosuccinic acidα-Iminosuccinateα-Iminosuccinic acidC4H5NO4131.0868131.0218576532-iminobutanedioic acidiminosuccinic acid79067-61-1OC(=O)CC(=N)C(O)=OInChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)NMUOATVLLQEYHI-UHFFFAOYSA-NSolidCytosollogp-0.83logs-1.49solubility4.26e+00 g/llogp-0.51pka_strongest_acidic3.28pka_strongest_basic2.48iupac2-iminobutanedioic acidaverage_mass131.0868mono_mass131.021857653smilesOC(=O)CC(=N)C(O)=OformulaC4H5NO4inchiInChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)inchikeyNMUOATVLLQEYHI-UHFFFAOYSA-Npolar_surface_area98.45refractivity36.81polarizability10.55rotatable_bond_count3acceptor_count5donor_count3physiological_charge-2formal_charge0Alanine, aspartate and glutamate metabolismec00250Nicotinate and nicotinamide metabolismec00760Metabolic pathwayseco01100NAD biosynthesisNicotinamide 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.
PW000829MetabolicNAD biosynthesis I (from aspartate)PYRIDNUCSYN-PWYSpecdb::CMs3108Specdb::CMs37940Specdb::CMs132222Specdb::CMs139956Specdb::NmrOneD259728Specdb::NmrOneD259729Specdb::NmrOneD259730Specdb::NmrOneD259731Specdb::NmrOneD259732Specdb::NmrOneD259733Specdb::NmrOneD259734Specdb::NmrOneD259735Specdb::NmrOneD259736Specdb::NmrOneD259737Specdb::NmrOneD259738Specdb::NmrOneD259739Specdb::NmrOneD259740Specdb::NmrOneD259741Specdb::NmrOneD259742Specdb::NmrOneD259743Specdb::NmrOneD259744Specdb::NmrOneD259745Specdb::NmrOneD259746Specdb::NmrOneD259747Specdb::MsMs28265Specdb::MsMs28266Specdb::MsMs28267Specdb::MsMs34823Specdb::MsMs34824Specdb::MsMs34825Specdb::MsMs2746079Specdb::MsMs2746080Specdb::MsMs2746081Specdb::MsMs2936776Specdb::MsMs2936777Specdb::MsMs2936778HMDB0113179613628208C05840IMINOASPARTATEKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064L-aspartate oxidaseP10902NADB_ECOLInadBhttp://ecmdb.ca/proteins/P10902.xmlQuinolinate synthase AP11458NADA_ECOLInadAhttp://ecmdb.ca/proteins/P11458.xmlDihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acidR04292QUINOLINATE-SYNTHA-RXNL-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acidRXN-9772L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidR00481L-ASPARTATE-OXID-RXNL-Aspartic acid + Ubiquinone-8 > Hydrogen ion + Iminoaspartic acid + Ubiquinol-8L-Aspartic acid + Menaquinone 8 > Hydrogen ion + Iminoaspartic acid + Menaquinol 8L-Aspartic acid + Oxygen <> Iminoaspartic acid + Hydrogen peroxideR00481L-ASPARTATE-OXID-RXNQuinolinic acid + 2 Water + Phosphate <> Iminoaspartic acid + Dihydroxyacetone phosphateR04292Oxygen + L-Aspartic acid > Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidL-ASPARTATE-OXID-RXNIminoaspartic acid + Dihydroxyacetone phosphate > Quinolinic acid + Water + PhosphateQUINOLINATE-SYNTHA-RXNDihydroxyacetone phosphate + Iminoaspartic acid > Quinolinic acid +2 Water + Inorganic phosphateL-Aspartic acid + Oxygen > Iminoaspartic acid + Hydrogen peroxideL-Aspartic acid + Oxygen + L-Aspartic acid > Hydrogen peroxide + Hydrogen ion + Iminoaspartic acidPW_R003007Iminoaspartic acid + Dihydroxyacetone phosphate > Phosphate +2 Water + Quinolinic acidPW_R003008L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidDihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acidQuinolinic acid + 2 Water + Phosphate <> Iminoaspartic acid + Dihydroxyacetone phosphateL-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidDihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid