1.0 2011-09-21 00:28:20 UTC 2025-11-19 02:43:48 UTC FDB023340 Pyrrole-2-carboxylic acid Pyrrole-2-carboxylic acid was synthesized over a century ago, but its history as a compound of biological origin is rather recent. It was first identified as a degradation product of sialic acids, then as a derivative of the oxidation of the D-hydroxyproline isomers by mammalian D-amino acid oxidase. The latter relationship results from the lability of the direct oxidation product, A'-pyrroline-4-hydroxy-2-carboxylic acid, which loses water spontaneously to form the pyrrole. A similar reaction is catalyzed by the more specific allohydroxy-D-proline oxidase of Pseudomonas. In whole animal observations, pyrrole-2-carboxylate (PCA) ' was identified in rat or human urine after administration of the D-isomers of hydroxyproline, a finding ascribable to the action of D-amino acid oxidase. (PMID: 4430715) Urinary excretion of N-(pyrrole-2-carboxyl) glycine has been reported in a 5-year-old affected with type II hyperprolinemia; The child has mild developmental delay, recurrent seizures of the grand mal type and EEG alterations. The urinary excretion of the conjugate is stressed, since it appears that only one previous report in the literature described this compound in the urine of two patients affected by this disturbance. (PMID 2383933) [HMDB] 1H-Pyrrole-2-carboxylic acid 1H-Pyrrole-2-carboxylic acid (9CI) 2-Minaline 2-Pyrrolecarboxylate 2-Pyrrolecarboxylic acid Minalin Minaline PCA PYC Pyrrole-2-carboxylate Pyrrole-2-carboxylic acid C5H5NO2 111.0987 111.032028409 1H-pyrrole-2-carboxylic acid minalin 634-97-9 OC(=O)C1=CC=CN1 InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8) WRHZVMBBRYBTKZ-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrrole 2-carboxylic acids. These are pyrrole carboxylic acids where the carboxyl group is attached at position C2. Pyrrole 2-carboxylic acids Organic compounds Organoheterocyclic compounds Pyrroles Pyrrole carboxylic acids and derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Substituted pyrroles Aromatic heteromonocyclic compound Azacycle Carboxylic acid Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrrole-2-carboxylic acid Substituted pyrrole pyrrolecarboxylic acid Solid logp 0.70 ALOGPS logs 0.17 ALOGPS solubility 1.64e+02 g/l ALOGPS logp 0.63 ChemAxon pka_strongest_acidic 5.16 ChemAxon iupac 1H-pyrrole-2-carboxylic acid ChemAxon average_mass 111.0987 ChemAxon mono_mass 111.032028409 ChemAxon smiles OC(=O)C1=CC=CN1 ChemAxon formula C5H5NO2 ChemAxon inchi InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8) ChemAxon inchikey WRHZVMBBRYBTKZ-UHFFFAOYSA-N ChemAxon polar_surface_area 53.09 ChemAxon refractivity 27.95 ChemAxon polarizability 10.24 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 1994 Specdb::NmrTwoD 1929 Specdb::MsIr 2173 Specdb::MsIr 2174 Specdb::MsIr 2175 Specdb::CMs 988 Specdb::CMs 1054 Specdb::CMs 7345 Specdb::CMs 31515 Specdb::CMs 31516 Specdb::CMs 32213 Specdb::CMs 38735 Specdb::CMs 173813 Specdb::MsMs 2376 Specdb::MsMs 2377 Specdb::MsMs 2378 Specdb::MsMs 6013 Specdb::MsMs 6014 Specdb::MsMs 6015 Specdb::MsMs 6016 Specdb::MsMs 6017 Specdb::MsMs 253065 Specdb::MsMs 253066 Specdb::MsMs 253067 Specdb::MsMs 273006 Specdb::MsMs 273007 Specdb::MsMs 273008 Specdb::MsMs 438364 Specdb::MsMs 438365 Specdb::MsMs 438366 Specdb::MsMs 438367 Specdb::MsMs 438368 Specdb::MsMs 2226785 Specdb::MsMs 2227956 Specdb::MsMs 2229183 Specdb::MsMs 2230257 Specdb::MsMs 2231655 Specdb::MsMs 2232559 HMDB04230 36751 #<Reference:0x000055ce2ed18d08> #<Reference:0x000055ce2ed18a88> #<Reference:0x000055ce2ed186a0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823