Record Information
Version1.0
Creation date2011-09-21 00:28:20 UTC
Update date2015-10-09 22:33:14 UTC
Primary IDFDB023340
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyrrole-2-carboxylic acid
DescriptionPyrrole-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]
CAS Number634-97-9
Structure
Thumb
Synonyms
SynonymSource
2-Pyrrolecarboxylic acidChEBI
MinalineChEBI
PCAChEBI
Pyrrole-2-carboxylateChEBI
2-PyrrolecarboxylateGenerator
2-Pyrrolecarboxylic acid, monosodium saltHMDB
1H-Pyrrole-2-carboxylic acidHMDB
1H-Pyrrole-2-carboxylic acid (9ci)HMDB
2-MinalineHMDB
MinalinHMDB
PYCHMDB
Pyrrole-2-carboxylic acidGenerator
1H-Pyrrole-2-carboxylic acid (9CI)hmdb
Predicted Properties
PropertyValueSource
Water Solubility164 g/LALOGPS
logP0.7ALOGPS
logP0.63ChemAxon
logS0.17ALOGPS
pKa (Strongest Acidic)5.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.95 m³·mol⁻¹ChemAxon
Polarizability10.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H5NO2
IUPAC name1H-pyrrole-2-carboxylic acid
InChI IdentifierInChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)
InChI KeyWRHZVMBBRYBTKZ-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC=CN1
Average Molecular Weight111.0987
Monoisotopic Molecular Weight111.032028409
Classification
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassPyrrole carboxylic acids and derivatives
Direct ParentPyrrole 2-carboxylic acids
Alternative Parents
Substituents
  • Pyrrole-2-carboxylic acid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPyrrole-2-carboxylic acid, 1 TMS, GC-MS Spectrumsplash10-00di-4900000000-efa4fc1d653090d2d0e4Spectrum
GC-MSPyrrole-2-carboxylic acid, 2 TMS, GC-MS Spectrumsplash10-00kf-2960000000-4cfedbfeebcc464b55cbSpectrum
GC-MSPyrrole-2-carboxylic acid, non-derivatized, GC-MS Spectrumsplash10-00kf-2960000000-4cfedbfeebcc464b55cbSpectrum
GC-MSPyrrole-2-carboxylic acid, non-derivatized, GC-MS Spectrumsplash10-00di-4900000000-efa4fc1d653090d2d0e4Spectrum
GC-MSPyrrole-2-carboxylic acid, non-derivatized, GC-MS Spectrumsplash10-00kg-1930000000-f3284be04e5e8bfeac8bSpectrum
Predicted GC-MSPyrrole-2-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03xu-9200000000-33ab2d86788b7fcdd4c5Spectrum
Predicted GC-MSPyrrole-2-carboxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-8900000000-03fc82d55f34cfc0748cSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9100000000-c1b7a81a7ce1be943119Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014l-9000000000-84e967fa699d0cafb578Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-b595715063572edc0dceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-1900000000-c7372bbc4222328a0fd1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-9000000000-bd5aa8d6918fc5699127Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-9000000000-7adfc180c9cd0187ef50Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-9000000000-26d8fa6604dcce168aceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014r-9000000000-d02c2068388d3953f43eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-c7372bbc4222328a0fd1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-bd5aa8d6918fc5699127Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-7adfc180c9cd0187ef50Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-d947b1d957c2f6581e1fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014r-9000000000-d02c2068388d3953f43eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-9800000000-2c170003a8d201c6eca8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-6eae79c5cb980732b059Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-71849ef71def20737bc9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-370eb1bf3ec71fa2ef1cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9400000000-5d37d525e8ded1560ddfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-5d4ed399bdbd9f14b497Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID11963
ChEMBL IDCHEMBL509027
KEGG Compound IDC05942
Pubchem Compound ID12473
Pubchem Substance IDNot Available
ChEBI ID36751
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04230
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPCA
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference