2.0 2012-05-31 13:46:24 -0600 2015-09-13 12:56:10 -0600 ECMDB01149 M2MDB000275 5-Aminolevulinic acid 5-Aminolevulinic acid is an intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway. δ-aminolevulinate δ-aminolevulinic acid γ-aminolevulinate γ-aminolevulinic acid 5-Amino-4-oxo-Pentanoate 5-Amino-4-oxo-Pentanoic acid 5-Amino-4-oxopentanoate 5-Amino-4-oxopentanoic acid 5-Amino-4-oxovalerate 5-Amino-4-oxovaleric acid 5-Amino-Levulinate 5-Amino-Levulinic acid 5-Aminolaevulinate 5-Aminolaevulinic acid 5-Aminolevulinate 5-aminolevulinic acid ALA Aladerm Amino-levulinate Amino-levulinic acid Aminolevulinate Aminolevulinic acid Delta-Aminolevulinate Delta-Aminolevulinic acid g-Aminolevulinate g-Aminolevulinic acid Gamma-Aminolevulinate Gamma-Aminolevulinic acid Kerastick γ-Aminolevulinate γ-Aminolevulinic acid δ-Aminolevulinate δ-Aminolevulinic acid C5H9NO3 131.1299 131.058243159 5-amino-4-oxopentanoic acid aminolevulinic acid 106-60-5 NCC(=O)CCC(O)=O InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) ZGXJTSGNIOSYLO-UHFFFAOYSA-N Solid Cytosol logp -2.85 ALOGPS logs 0.12 ALOGPS solubility 1.73e+02 g/l ALOGPS melting_point 156-158 oC logp -3.3 ChemAxon pka_strongest_acidic 4.05 ChemAxon pka_strongest_basic 7.84 ChemAxon iupac 5-amino-4-oxopentanoic acid ChemAxon average_mass 131.1299 ChemAxon mono_mass 131.058243159 ChemAxon smiles NCC(=O)CCC(O)=O ChemAxon formula C5H9NO3 ChemAxon inchi InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) ChemAxon inchikey ZGXJTSGNIOSYLO-UHFFFAOYSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 30.45 ChemAxon polarizability 12.55 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glycine, serine and threonine metabolism ec00260 Porphyrin and chlorophyll metabolism ec00860 ABC transporters ec02010 Metabolic pathways eco01100 Porphyrin metabolism The 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. PW000936 Metabolic tetrapyrrole biosynthesis I PWY-5188 Specdb::CMs 701 Specdb::CMs 702 Specdb::CMs 703 Specdb::CMs 704 Specdb::CMs 705 Specdb::CMs 706 Specdb::CMs 1427 Specdb::CMs 1457 Specdb::CMs 3255 Specdb::CMs 30332 Specdb::CMs 30333 Specdb::CMs 30457 Specdb::CMs 30458 Specdb::CMs 30917 Specdb::CMs 30918 Specdb::CMs 31281 Specdb::CMs 31282 Specdb::CMs 37948 Specdb::CMs 174789 Specdb::NmrOneD 1650 Specdb::NmrOneD 146630 Specdb::NmrOneD 146631 Specdb::NmrOneD 146632 Specdb::NmrOneD 146633 Specdb::NmrOneD 146634 Specdb::NmrOneD 146635 Specdb::NmrOneD 146636 Specdb::NmrOneD 146637 Specdb::NmrOneD 146638 Specdb::NmrOneD 146639 Specdb::NmrOneD 146640 Specdb::NmrOneD 146641 Specdb::NmrOneD 146642 Specdb::NmrOneD 146643 Specdb::NmrOneD 146644 Specdb::NmrOneD 146645 Specdb::NmrOneD 146646 Specdb::NmrOneD 146647 Specdb::NmrOneD 146648 Specdb::NmrOneD 146649 Specdb::MsMs 1433 Specdb::MsMs 1434 Specdb::MsMs 1435 Specdb::MsMs 5049 Specdb::MsMs 5050 Specdb::MsMs 5051 Specdb::MsMs 5052 Specdb::MsMs 5053 Specdb::MsMs 5060 Specdb::MsMs 5061 Specdb::MsMs 20222 Specdb::MsMs 20223 Specdb::MsMs 20224 Specdb::MsMs 20249 Specdb::MsMs 20250 Specdb::MsMs 20251 Specdb::MsMs 21773 Specdb::MsMs 21774 Specdb::MsMs 21775 Specdb::MsMs 21800 Specdb::MsMs 21801 Specdb::MsMs 21802 Specdb::MsMs 439128 Specdb::MsMs 445596 Specdb::MsMs 445597 Specdb::NmrTwoD 1591 HMDB01149 137 134 C00430 17549 5-AMINO-LEVULINATE 5-Aminolevulinic acid Keseler, I. 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Photochem Photobiol. 1997 Jul;66(1):114-8. 9230710 Goli?ski J., D?browski Z., Obukowicz B., Kami?ski J., Be?dowicz M., Kwa?ny M.: "Synthesis of 5-aminolevulinic acid (5-ALA)", ICRI Annual Report '99, 2000, 119-122. http://hmdb.ca/system/metabolites/msds/000/001/032/original/HMDB01149.pdf?1358461682 Delta-aminolevulinic acid dehydratase P0ACB2 HEM2_ECOLI hemB http://ecmdb.ca/proteins/P0ACB2.xml Glutamate-1-semialdehyde 2,1-aminomutase P23893 GSA_ECOLI hemL http://ecmdb.ca/proteins/P23893.xml (S)-4-Amino-5-oxopentanoate <> 5-Aminolevulinic acid R02272 GSAAMINOTRANS-RXN 2 5-Aminolevulinic acid <> Hydrogen ion +2 Water + Porphobilinogen R00036 PORPHOBILSYNTH-RXN 2 5-Aminolevulinic acid <> Porphobilinogen +2 Water R00036 5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoate R02272 GSAAMINOTRANS-RXN 5-Aminolevulinic acid <> Hydrogen ion + Water + Porphobilinogen R00036 PORPHOBILSYNTH-RXN (S)-4-Amino-5-oxopentanoate > 5-Aminolevulinic acid 2 5-Aminolevulinic acid > Porphobilinogen +2 Water 8 (S)-4-Amino-5-oxopentanoate >8 5-Aminolevulinic acid PW_R003474 8 5-Aminolevulinic acid >4 Hydrogen ion +8 Water +4 Porphobilinogen PW_R003475 (S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid 5 5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoate 2 5-Aminolevulinic acid <> Hydrogen ion +2 Water + Porphobilinogen 2 5-Aminolevulinic acid <> Porphobilinogen +2 Water (S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid 2 5-Aminolevulinic acid <> Hydrogen ion +2 Water + Porphobilinogen