2.0 2012-05-31 13:00:48 -0600 2015-09-13 12:56:09 -0600 ECMDB00725 M2MDB000179 Hydroxyproline Hydroxyproline is a common proteinogenic amino acid. Hydroxyproline differs from proline by the presence of a hydroxyl (OH) group attached to the C (gamma) atom. Hydroxyproline differs from proline by the presence of a hydroxyl (OH) group attached to the C (gamma) atom. It is produced by hydroxylation of the amino acid proline. It is not directly coded for by DNA, however, and is hydroxylated after protein synthesis. (Wikipedia) (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylate (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid (2S,4R)-4-hydroxypyrrolidine-2-carboxylate (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid (4R)-4-hydroxy-L-proline 4-Hydroxy-2-pyrrolidinecarboxylate 4-Hydroxy-2-pyrrolidinecarboxylic acid 4-Hydroxy-L-proline 4-Hydroxyproline 4-L-Hydroxyproline Delta-Hydroxyproline Hydroxiproline Hydroxy-L-proline Hydroxy-proline Hydroxyproline L-4-Hydroxyproline L-Hydroxyproline L-Threo-4-hydroxyproline LS-hydroxyproline Oxaceprol Trans-4-Hydroxy-L-proline Trans-4-Hydroxyproline Trans-hydroxyproline Trans-L-hydroxyproline δ-Hydroxyproline C5H9NO3 131.1299 131.058243159 (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid hypro 51-35-4 O[C@H]1CN[C@@H](C1)C(O)=O InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 PMMYEEVYMWASQN-DMTCNVIQSA-N Solid Cytoplasm Periplasm logp -3.31 ALOGPS logs 0.57 ALOGPS solubility 4.92e+02 g/l ALOGPS melting_point 274-275 oC logp -3.7 ChemAxon pka_strongest_acidic 1.64 ChemAxon pka_strongest_basic 10.62 ChemAxon iupac (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ChemAxon average_mass 131.1299 ChemAxon mono_mass 131.058243159 ChemAxon smiles O[C@H]1CN[C@@H](C1)C(O)=O ChemAxon formula C5H9NO3 ChemAxon inchi InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 ChemAxon inchikey PMMYEEVYMWASQN-DMTCNVIQSA-N ChemAxon polar_surface_area 69.56 ChemAxon refractivity 29.38 ChemAxon polarizability 12.29 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Specdb::CMs 625 Specdb::CMs 626 Specdb::CMs 627 Specdb::CMs 1160 Specdb::CMs 1212 Specdb::CMs 2536 Specdb::CMs 30060 Specdb::CMs 30701 Specdb::CMs 30805 Specdb::CMs 31214 Specdb::CMs 31215 Specdb::CMs 31837 Specdb::CMs 31838 Specdb::CMs 31839 Specdb::CMs 37723 Specdb::CMs 170170 Specdb::CMs 1072785 Specdb::CMs 1072786 Specdb::CMs 1072788 Specdb::CMs 1072790 Specdb::CMs 1072792 Specdb::CMs 1072794 Specdb::CMs 1072795 Specdb::CMs 1072797 Specdb::CMs 1072799 Specdb::EiMs 1984 Specdb::NmrOneD 1263 Specdb::NmrOneD 1501 Specdb::NmrOneD 4955 Specdb::NmrOneD 166503 Specdb::NmrOneD 166594 Specdb::MsMs 1017 Specdb::MsMs 1018 Specdb::MsMs 1019 Specdb::MsMs 4548 Specdb::MsMs 4549 Specdb::MsMs 178380 Specdb::MsMs 178381 Specdb::MsMs 178382 Specdb::MsMs 180699 Specdb::MsMs 180700 Specdb::MsMs 180701 Specdb::MsMs 439113 Specdb::MsMs 440070 Specdb::MsMs 440077 Specdb::MsMs 447334 Specdb::MsMs 448070 Specdb::MsMs 451900 Specdb::MsMs 451909 Specdb::MsMs 2226802 Specdb::MsMs 2227892 Specdb::MsMs 2229166 Specdb::MsMs 2230309 Specdb::MsMs 2231591 Specdb::MsMs 2232584 Specdb::MsMs 2234040 Specdb::NmrTwoD 1034 Specdb::NmrTwoD 1447 HMDB00725 5810 5605 C01157 18095 L-4-HYDROXY-PROLINE HYP Hydroxyproline Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. 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Journal of Biological Chemistry (1960), 235 3492-8. http://hmdb.ca/system/metabolites/msds/000/000/644/original/HMDB00725.pdf?1358463273 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 Luria-Bertani (LB) media Shake flask 0.31 uM true 0.04 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 1225 146 Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602. 17535911