2.02012-05-31 14:23:05 -06002015-06-03 17:19:08 -0600ECMDB20017M2MDB000866(S)-4-Amino-5-oxopentanoate(s)-4-amino-5-oxopentanoate is a member of the chemical class known as Gamma Amino Acids and Derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. (S)-4-amino-5-oxopentanoate(S)-4-amino-5-oxopentanoic acidGluSAL-Glutamate 1-semialdehydeL-Glutamic acid 1-semialdehydeC5H9NO3131.1299131.058243159(4S)-4-amino-5-oxopentanoic acidglutamate-1-semialdehyde[H][C@](N)(CCC(O)=O)C=OInChI=1S/C5H9NO3/c6-4(3-7)1-2-5(8)9/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1MPUUQNGXJSEWTF-BYPYZUCNSA-NCytosollogp-2.91logs0.04solubility1.43e+02 g/llogp-3.4pka_strongest_acidic4.03pka_strongest_basic8.1iupac(4S)-4-amino-5-oxopentanoic acidaverage_mass131.1299mono_mass131.058243159smiles[H][C@](N)(CCC(O)=O)C=OformulaC5H9NO3inchiInChI=1S/C5H9NO3/c6-4(3-7)1-2-5(8)9/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1inchikeyMPUUQNGXJSEWTF-BYPYZUCNSA-Npolar_surface_area80.39refractivity30.36polarizability12.44rotatable_bond_count4acceptor_count4donor_count2physiological_charge0formal_charge0Porphyrin and chlorophyll metabolismec00860Metabolic pathwayseco01100Porphyrin metabolismThe metabolism of porphyrin begins with with glutamic acid being processed by an ATP-driven glutamyl-tRNA synthetase by interacting with hydrogen ion and tRNA(Glu), resulting in amo, pyrophosphate and L-glutamyl-tRNA(Glu) Glutamic acid. Glutamic acid can be obtained as a result of L-glutamate metabolism pathway, glutamate / aspartate : H+ symporter GltP, glutamate:sodium symporter or a glutamate / aspartate ABC transporter .
L-glutamyl-tRNA(Glu) Glutamic acid interacts with a NADPH glutamyl-tRNA reductase resulting in a NADP, a tRNA(Glu) and a (S)-4-amino-5-oxopentanoate.
This compound interacts with a glutamate-1-semialdehyde aminotransferase resulting a 5-aminolevulinic acid. This compound interacts with a porphobilinogen synthase resulting in a hydrogen ion, water and porphobilinogen. The latter compound interacts with water resulting in hydroxymethylbilane synthase resulting in ammonium, and hydroxymethylbilane.
Hydroxymethylbilane can either be dehydrated to produce uroporphyrinogen I or interact with a uroporphyrinogen III synthase resulting in a water molecule and a uroporphyrinogen III.
Uroporphyrinogen I interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a coproporphyrinogen I
Uroporphyrinogen III can be metabolized into precorrin by interacting with a S-adenosylmethionine through a siroheme synthase resulting in hydrogen ion, an s-adenosylhomocysteine and a precorrin-1. On the other hand, Uroporphyrinogen III interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a Coproporphyrinogen III.
Precorrin-1 reacts with a S-adenosylmethionine through a siroheme synthase resulting in a S-adenosylhomocysteine and a Precorrin-2. The latter compound is processed by a NAD dependent uroporphyrin III C-methyltransferase [multifunctional] resulting in a NADH and a sirohydrochlorin. This compound then interacts with Fe 2+
uroporphyrin III C-methyltransferase [multifunctional] resulting in a hydrogen ion and a siroheme. The siroheme is then processed in sulfur metabolism pathway.
Uroporphyrinogen III can be processed in anaerobic or aerobic condition.
Anaerobic:
Uroporphyrinogen III interacts with an oxygen molecule, a hydrogen ion through a coproporphyrinogen III oxidase resulting in water, carbon dioxide and protoporphyrinogen IX. The latter compound then interacts with an 3 oxygen molecule through a protoporphyrinogen oxidase resulting in 3 hydrogen peroxide and a Protoporphyrin IX
Aerobic:
Uroporphyrinogen III reacts with S-adenosylmethionine through a coproporphyrinogen III dehydrogenase resulting in carbon dioxide, 5-deoxyadenosine, L-methionine and protoporphyrinogen IX. The latter compound interacts with a meanquinone through a protoporphyrinogen oxidase resulting in protoporphyrin IX.
The protoporphyrin IX interacts with Fe 2+ through a ferrochelatase resulting in a hydrogen ion and a ferroheme b. The ferroheme b can either be incorporated into the oxidative phosphorylation as a cofactor of the enzymes involved in that pathway or it can interact with hydrogen peroxide through a catalase HPII resulting in a heme D. Heme D can then be incorporated into the oxidative phosphyrlation pathway as a cofactor of the enzymes involved in that pathway. Ferroheme b can also interact with water and a farnesyl pyrophosphate through a heme O synthase resulting in a release of pyrophosphate and heme O. Heme O is then incorporated into the Oxidative phosphorylation pathway.
PW000936Metabolictetrapyrrole biosynthesis IPWY-5188Specdb::CMs1086951Specdb::NmrOneD322752Specdb::NmrOneD322753Specdb::NmrOneD322754Specdb::NmrOneD322755Specdb::NmrOneD322756Specdb::NmrOneD322757Specdb::NmrOneD322758Specdb::NmrOneD322759Specdb::NmrOneD322760Specdb::NmrOneD322761Specdb::NmrOneD322762Specdb::NmrOneD322763Specdb::NmrOneD322764Specdb::NmrOneD322765Specdb::NmrOneD322766Specdb::NmrOneD322767Specdb::NmrOneD322768Specdb::NmrOneD322769Specdb::NmrOneD322770Specdb::NmrOneD322771Specdb::MsMs28379Specdb::MsMs28380Specdb::MsMs28381Specdb::MsMs34937Specdb::MsMs34938Specdb::MsMs34939742114525C0374115757GLUTAMATE-1-SEMIALDEHYDEGLU_LSN3_DHE2Keseler, 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-D114.22080510Glutamyl-tRNA reductaseP0A6X1HEM1_ECOLIhemAhttp://ecmdb.ca/proteins/P0A6X1.xmlGlutamate-1-semialdehyde 2,1-aminomutaseP23893GSA_ECOLIhemLhttp://ecmdb.ca/proteins/P23893.xml(S)-4-Amino-5-oxopentanoate <> 5-Aminolevulinic acidR02272GSAAMINOTRANS-RXNL-Glutamyl-tRNA(Glu) + Hydrogen ion + NADPH > (S)-4-Amino-5-oxopentanoate + NADP + tRNA (Glu)5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoateR02272GSAAMINOTRANS-RXNL-Glutamyl-tRNA(Glu) + NADPH + Hydrogen ion + tRNA(Glu) <> (S)-4-Amino-5-oxopentanoate + tRNA(Glu) + NADP + L-Glutamyl-tRNA(Glu)R04109(S)-4-Amino-5-oxopentanoate > 5-Aminolevulinic acid(S)-4-Amino-5-oxopentanoate + NADP + tRNA(Glu) > L-glutamyl-tRNA(Glu) + NADPH8 L-glutamyl-tRNA(Glu) + 8 NADPH + 8 NADPH >8 tRNA(Glu) +8 NADP +8 (S)-4-Amino-5-oxopentanoatePW_R0034738 (S)-4-Amino-5-oxopentanoate >8 5-Aminolevulinic acidPW_R003474(S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid5 5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoateL-Glutamyl-tRNA(Glu) + NADPH + Hydrogen ion + tRNA(Glu) <> (S)-4-Amino-5-oxopentanoate + NADP(S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid