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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 14:52:55 UTC
Update Date2021-09-07 16:45:36 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
1H-Pyrrole-2-carboxylic acidHMDB
1H-Pyrrole-2-carboxylic acid (9ci)HMDB
2-MinalineHMDB
MinalinHMDB
PYCHMDB
2-Pyrrolecarboxylic acid, monosodium saltMeSH, HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.85POMONA (1987)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available114.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00002133
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.21531661259
DarkChem[M-H]-115.17731661259
DeepCCS[M+H]+119.82630932474
DeepCCS[M-H]-117.33430932474
DeepCCS[M-2H]-153.82230932474
DeepCCS[M+Na]+128.53430932474
AllCCS[M+H]+123.232859911
AllCCS[M+H-H2O]+118.232859911
AllCCS[M+NH4]+127.832859911
AllCCS[M+Na]+129.132859911
AllCCS[M-H]-117.532859911
AllCCS[M+Na-2H]-120.032859911
AllCCS[M+HCOO]-122.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pyrrole-2-carboxylic acidOC(=O)C1=CC=CN12490.6Standard polar33892256
Pyrrole-2-carboxylic acidOC(=O)C1=CC=CN11140.6Standard non polar33892256
Pyrrole-2-carboxylic acidOC(=O)C1=CC=CN11255.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrrole-2-carboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C[NH]11229.7Semi standard non polar33892256
Pyrrole-2-carboxylic acid,1TMS,isomer #2C[Si](C)(C)N1C=CC=C1C(=O)O1333.6Semi standard non polar33892256
Pyrrole-2-carboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN1[Si](C)(C)C1355.8Semi standard non polar33892256
Pyrrole-2-carboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN1[Si](C)(C)C1444.4Standard non polar33892256
Pyrrole-2-carboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN1[Si](C)(C)C1496.6Standard polar33892256
Pyrrole-2-carboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C[NH]11472.4Semi standard non polar33892256
Pyrrole-2-carboxylic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CC=C1C(=O)O1573.8Semi standard non polar33892256
Pyrrole-2-carboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C1844.9Semi standard non polar33892256
Pyrrole-2-carboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C1840.0Standard non polar33892256
Pyrrole-2-carboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C1767.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (1 TMS)splash10-00di-4900000000-efa4fc1d653090d2d0e42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (2 TMS)splash10-00kf-2960000000-4cfedbfeebcc464b55cb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (Non-derivatized)splash10-00kf-2960000000-4cfedbfeebcc464b55cb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (Non-derivatized)splash10-00di-4900000000-efa4fc1d653090d2d0e42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrrole-2-carboxylic acid GC-EI-TOF (Non-derivatized)splash10-00kg-1930000000-f3284be04e5e8bfeac8b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-9200000000-33ab2d86788b7fcdd4c52017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-8900000000-03fc82d55f34cfc0748c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrole-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-9100000000-c1b7a81a7ce1be9431192012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014l-9000000000-84e967fa699d0cafb5782012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-9000000000-b595715063572edc0dce2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0a4i-1900000000-c7372bbc4222328a0fd12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-014i-9000000000-bd5aa8d6918fc56991272012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-014i-9000000000-7adfc180c9cd0187ef502012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-014i-9000000000-26d8fa6604dcce168ace2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-014r-9000000000-d02c2068388d3953f43e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-1900000000-c7372bbc4222328a0fd12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ , negative-QTOFsplash10-014i-9000000000-bd5aa8d6918fc56991272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ , negative-QTOFsplash10-014i-9000000000-7adfc180c9cd0187ef502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ , negative-QTOFsplash10-014i-9000000000-d947b1d957c2f6581e1f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid LC-ESI-QQ , negative-QTOFsplash10-014r-9000000000-d02c2068388d3953f43e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 20V, Negative-QTOFsplash10-014i-9000000000-a2af5bd2aa42260c720f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 10V, Negative-QTOFsplash10-014i-9000000000-f14d9350f9dab98d12092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 40V, Positive-QTOFsplash10-0006-9000000000-f6aeaa6f98bd998f78a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 35V, Negative-QTOFsplash10-014i-9000000000-068e8b4c4ccf0f4dcd922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 10V, Positive-QTOFsplash10-03di-4900000000-f6d2c4c13ec24df8abcb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 35V, Positive-QTOFsplash10-0002-9200000000-c7f0b11c04224c0dced02021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 10V, Positive-QTOFsplash10-03dl-9800000000-2c170003a8d201c6eca82017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 20V, Positive-QTOFsplash10-014i-9100000000-6eae79c5cb980732b0592017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 40V, Positive-QTOFsplash10-014l-9000000000-71849ef71def20737bc92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 10V, Negative-QTOFsplash10-03di-5900000000-370eb1bf3ec71fa2ef1c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 20V, Negative-QTOFsplash10-03xr-9400000000-5d37d525e8ded1560ddf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole-2-carboxylic acid 40V, Negative-QTOFsplash10-00kf-9000000000-5d4ed399bdbd9f14b4972017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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. 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 ]
  2. 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 ]
  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 ]