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Record Information
Version3.6
Creation Date2006-08-13 14:52:55 UTC
Update Date2016-02-11 01:06:38 UTC
HMDB IDHMDB04230
Secondary Accession Numbers
  • HMDB03094
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
Thumb
Synonyms
ValueSource
2-Pyrrolecarboxylic acidChEBI
PCAChEBI
Pyrrole-2-carboxylateChEBI
2-PyrrolecarboxylateGenerator
1H-Pyrrole-2-carboxylateGenerator
Pyrrole-2-carboxylic acidGenerator
1H-Pyrrole-2-carboxylic acid (9ci)HMDB
2-MinalineHMDB
MinalinHMDB
MinalineHMDB
PYCHMDB
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 KeyInChIKey=WRHZVMBBRYBTKZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
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 Solubility164.0 mg/mLALOGPS
logP0.7ALOGPS
logP0.63ChemAxon
logS0.17ALOGPS
pKa (Strongest Acidic)3.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.95 m3·mol-1ChemAxon
Polarizability10.24 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-4900000000-efa4fc1d653090d2d0e4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kf-2960000000-4cfedbfeebcc464b55cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9100000000-c1b7a81a7ce1be943119View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014l-9000000000-84e967fa699d0cafb578View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-b595715063572edc0dceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-1900000000-c7372bbc4222328a0fd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-9000000000-bd5aa8d6918fc5699127View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-9000000000-7adfc180c9cd0187ef50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-9000000000-26d8fa6604dcce168aceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014r-9000000000-d02c2068388d3953f43eView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>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 IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023340
KNApSAcK IDNot Available
Chemspider ID11963
KEGG Compound IDC05942
BioCyc IDCPD-478
BiGG IDNot Available
Wikipedia LinkPCA
NuGOwiki LinkHMDB04230
Metagene LinkHMDB04230
METLIN ID3787
PubChem Compound12473
PDB IDNot Available
ChEBI ID36751
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. [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. [235519 ]
  3. Heacock AM, Adams E: Formation and excretion of pyrrole-2-carboxylate in man. J Clin Invest. 1974 Oct;54(4):810-8. [4430715 ]