1.02011-09-21 00:28:20 UTC2015-10-09 22:33:14 UTCFDB023340Pyrrole-2-carboxylic acidPyrrole-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 acid1H-Pyrrole-2-carboxylic acid (9CI)2-Minaline2-Pyrrolecarboxylate2-Pyrrolecarboxylic acidMinalinMinalinePCAPYCPyrrole-2-carboxylatePyrrole-2-carboxylic acidC5H5NO2111.0987111.032028409634-97-9OC(=O)C1=CC=CN1InChI=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 acidsOrganic compoundsOrganoheterocyclic compoundsPyrrolesPyrrole carboxylic acids and derivativesAromatic heteromonocyclic compoundsAzacyclic compoundsCarboxylic acidsHeteroaromatic compoundsHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOrganonitrogen compoundsOrganooxygen compoundsOrganopnictogen compoundsSubstituted pyrrolesAromatic heteromonocyclic compoundAzacycleCarboxylic acidCarboxylic acid derivativeHeteroaromatic compoundHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPyrrole-2-carboxylic acidSubstituted pyrrolepyrrolecarboxylic acidSolidaverage_mass111.0987mono_mass111.032028409smilesOC(=O)C1=CC=CN1formulaC5H5NO2inchiInChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)inchikeyWRHZVMBBRYBTKZ-UHFFFAOYSA-NSpecdb::NmrOneD1994Specdb::NmrTwoD1929Specdb::MsIr2173Specdb::MsIr2174Specdb::MsIr2175Specdb::CMs988Specdb::CMs1054Specdb::CMs7345Specdb::CMs31515Specdb::CMs31516Specdb::CMs32213Specdb::CMs38735Specdb::CMs173813Specdb::MsMs2376Specdb::MsMs2377Specdb::MsMs2378Specdb::MsMs6013Specdb::MsMs6014Specdb::MsMs6015Specdb::MsMs6016Specdb::MsMs6017Specdb::MsMs253065Specdb::MsMs253066Specdb::MsMs253067Specdb::MsMs273006Specdb::MsMs273007Specdb::MsMs273008Specdb::MsMs438364Specdb::MsMs438365Specdb::MsMs438366Specdb::MsMs438367Specdb::MsMs438368Specdb::MsMs2226785Specdb::MsMs2227956Specdb::MsMs2229183Specdb::MsMs2230257Specdb::MsMs2231655Specdb::MsMs2232559HMDB0423036751#<Reference:0x0000555674e22000>#<Reference:0x0000555674e21e20>#<Reference:0x0000555674e21b78>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823