You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 14:52:55 UTC
Update Date2020-02-26 21:25:03 UTC
HMDB IDHMDB0004230
Secondary Accession Numbers
  • HMDB0003094
  • HMDB03094
  • HMDB04230
Metabolite Identification
Common 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 ).
Structure
Data?1582752303
Synonyms
ValueSource
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
Chemical FormulaC5H5NO2
Average Molecular Weight111.0987
Monoisotopic Molecular Weight111.032028409
IUPAC Name1H-pyrrole-2-carboxylic acid
Traditional Nameminalin
CAS Registry Number634-97-9
SMILES
OC(=O)C1=CC=CN1
InChI Identifier
InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)
InChI KeyWRHZVMBBRYBTKZ-UHFFFAOYSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.85POMONA (1987)
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-4900000000-efa4fc1d653090d2d0e4Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kf-2960000000-4cfedbfeebcc464b55cbSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kf-2960000000-4cfedbfeebcc464b55cbSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-4900000000-efa4fc1d653090d2d0e4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kg-1930000000-f3284be04e5e8bfeac8bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-9200000000-33ab2d86788b7fcdd4c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-8900000000-03fc82d55f34cfc0748cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9100000000-c1b7a81a7ce1be943119Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014l-9000000000-84e967fa699d0cafb578Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-b595715063572edc0dceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-1900000000-c7372bbc4222328a0fd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-9000000000-bd5aa8d6918fc5699127Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-9000000000-7adfc180c9cd0187ef50Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-9000000000-26d8fa6604dcce168aceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014r-9000000000-d02c2068388d3953f43eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-c7372bbc4222328a0fd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-bd5aa8d6918fc5699127Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-7adfc180c9cd0187ef50Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-d947b1d957c2f6581e1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014r-9000000000-d02c2068388d3953f43eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-9800000000-2c170003a8d201c6eca8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-6eae79c5cb980732b059Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-71849ef71def20737bc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-370eb1bf3ec71fa2ef1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9400000000-5d37d525e8ded1560ddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-5d4ed399bdbd9f14b497Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.03 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02543
Phenol Explorer Compound IDNot Available
FooDB IDFDB023340
KNApSAcK IDC00043859
Chemspider ID11963
KEGG Compound IDC05942
BioCyc IDCPD-478
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3787
PubChem Compound12473
PDB IDNot Available
ChEBI ID36751
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceKosugi, Yoshio. Pyrrole-2-carboxylic acids and manufacturing methods therefor. Jpn. Kokai Tokkyo Koho (2002), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Heacock AM, Adams E: Formation and excretion of pyrrole-2-carboxylic acid. Whole animal and enzyme studies in the rat. J Biol Chem. 1975 Apr 10;250(7):2599-608. [PubMed:235519 ]
  2. Wajner M, Wannmacher CM, Purkiss P: High urinary excretion of N-(pyrrole-2-carboxyl) glycine in type II hyperprolinemia. Clin Genet. 1990 Jun;37(6):485-9. [PubMed:2383933 ]
  3. Heacock AM, Adams E: Formation and excretion of pyrrole-2-carboxylate in man. J Clin Invest. 1974 Oct;54(4):810-8. [PubMed:4430715 ]