2.0 2012-05-31 13:51:04 -0600 2015-06-03 15:53:58 -0600 ECMDB01369 M2MDB000359 Pyrroline hydroxycarboxylic acid Pyrroline hydroxycarboxylic acid is an intermediate in arginine and proline metabolism. It is converted to trans-4-hydroxy-L-proline via pyrroline-5-carboxylate reductase, and to L-erythro-4-Hydroxyglutamate via delta-1-pyrroline-5-carboxylate dehydrogenase. (KEGG) (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate (3R,5S)-1-Pyrroline-3-hydroxy-5-carboxylic acid 3-Hydroxy-L-1-pyrroline-5-carboxylate 3-Hydroxy-L-1-pyrroline-5-carboxylic acid L-&Delta;1-pyrroline 3-hydroxy-5-carboxylate L-&Delta;1-pyrroline 3-hydroxy-5-carboxylic acid L-&Delta;<SUP>1</SUP>-pyrroline 3-hydroxy-5-carboxylate L-1-Pyrroline 3-hydroxy-5-carboxylate L-1-Pyrroline 3-hydroxy-5-carboxylic acid L-1-Pyrroline-3-hydroxy-5-carboxylate L-1-Pyrroline-3-hydroxy-5-carboxylic acid L-1pyrroline-3-hydroxy-5-carboxylate L-1Pyrroline-3-hydroxy-5-carboxylic acid L-Delta1-pyrroline 3-hydroxy-5-carboxylate L-Delta1-pyrroline 3-hydroxy-5-carboxylic acid L-δ1-Pyrroline 3-hydroxy-5-carboxylate L-δ1-Pyrroline 3-hydroxy-5-carboxylic acid Pyrroline hydroxycarboxylate Pyrroline-hydroxy-carboxylate Pyrroline-hydroxy-carboxylic acid C5H7NO3 129.114 129.042593095 4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid pyrroline-hydroxy-carboxylate 22573-88-2 OC1CC(N=C1)C(O)=O InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9) WFOFKRKDDKGRIK-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -1.10 ALOGPS logs -0.58 ALOGPS solubility 3.39e+01 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 3.72 ChemAxon pka_strongest_basic 2.59 ChemAxon iupac 4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid ChemAxon average_mass 129.114 ChemAxon mono_mass 129.042593095 ChemAxon smiles OC1CC(N=C1)C(O)=O ChemAxon formula C5H7NO3 ChemAxon inchi InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9) ChemAxon inchikey WFOFKRKDDKGRIK-UHFFFAOYSA-N ChemAxon polar_surface_area 69.89 ChemAxon refractivity 28.85 ChemAxon polarizability 11.6 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Specdb::CMs 2714 Specdb::CMs 38042 Specdb::CMs 165574 Specdb::NmrOneD 147570 Specdb::NmrOneD 147571 Specdb::NmrOneD 147572 Specdb::NmrOneD 147573 Specdb::NmrOneD 147574 Specdb::NmrOneD 147575 Specdb::NmrOneD 147576 Specdb::NmrOneD 147577 Specdb::NmrOneD 147578 Specdb::NmrOneD 147579 Specdb::NmrOneD 147580 Specdb::NmrOneD 147581 Specdb::NmrOneD 147582 Specdb::NmrOneD 147583 Specdb::NmrOneD 147584 Specdb::NmrOneD 147585 Specdb::NmrOneD 147586 Specdb::NmrOneD 147587 Specdb::NmrOneD 147588 Specdb::NmrOneD 147589 Specdb::MsMs 1537 Specdb::MsMs 178719 Specdb::MsMs 178720 Specdb::MsMs 178721 Specdb::MsMs 181038 Specdb::MsMs 181039 Specdb::MsMs 181040 Specdb::MsMs 2398137 Specdb::MsMs 2398138 Specdb::MsMs 2398139 Specdb::MsMs 2536784 Specdb::MsMs 2536785 Specdb::MsMs 2536786 HMDB01369 1059 1030 C04281 PYRROLINE-HYDROXY-CARBOXYLATE Kanehisa, 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. 22080510 Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81. 533224 Onenli-Mungan N, Yuksel B, Elkay M, Topaloglu AK, Baykal T, Ozer G: Type II hyperprolinemia: a case report. Turk J Pediatr. 2004 Apr-Jun;46(2):167-9. 15214748 Valle D, Goodman SI, Harris SC, Phang JM: Genetic evidence for a common enzyme catalyzing the second step in the degradation of proline and hydroxyproline. J Clin Invest. 1979 Nov;64(5):1365-70. 500817 Bifunctional protein putA P09546 PUTA_ECOLI putA http://ecmdb.ca/proteins/P09546.xml Pyrroline-5-carboxylate reductase P0A9L8 P5CR_ECOLI proC http://ecmdb.ca/proteins/P0A9L8.xml Hydroxyproline + NAD <> Pyrroline hydroxycarboxylic acid + NADH + Hydrogen ion R03291 Hydroxyproline + NADP <> Pyrroline hydroxycarboxylic acid + NADPH + Hydrogen ion R03293 Pyrroline hydroxycarboxylic acid + NAD + 2 Water <> L-erythro-4-Hydroxyglutamate + NADH + Hydrogen ion R04444 Pyrroline hydroxycarboxylic acid + NADP + 2 Water <> L-erythro-4-Hydroxyglutamate + NADPH + Hydrogen ion R04445