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Record Information
Version2.0
Created at2006-08-13 14:52:55 UTC
Updated at2021-10-07 20:41:45 UTC
NP-MRD IDNP0001450
Secondary Accession NumbersNone
Natural Product 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
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 Mass111.0987 Da
Monoisotopic Mass111.03203 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brachystemma calycinumLOTUS Database
Bubalus bubalisFooDB
Capparis spinosaLOTUS Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chlamydomonas reinhardtiiLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Marasmiellus ramealisLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pseudostellaria heterophyllaKNApSAcK Database
Streptomyces griseoflavusLOTUS Database
Streptomyces griseusLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Streptomyces sp. GW23/1540KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.85Not Available
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
HMDB IDHMDB0004230
DrugBank IDDB02543
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  4. Kiew LV, Chang CY, Huang SY, Wang PW, Heh CH, Liu CT, Cheng CH, Lu YX, Chen YC, Huang YX, Chang SY, Tsai HY, Kung YA, Huang PN, Hsu MH, Leo BF, Foo YY, Su CH, Hsu KC, Huang PH, Ng CJ, Kamarulzaman A, Yuan CJ, Shieh DB, Shih SR, Chung LY, Chang CC: Development of flexible electrochemical impedance spectroscopy-based biosensing platform for rapid screening of SARS-CoV-2 inhibitors. Biosens Bioelectron. 2021 Jul 1;183:113213. doi: 10.1016/j.bios.2021.113213. Epub 2021 Apr 3. [PubMed:33857754 ]
  5. Payne KAP, Marshall SA, Fisher K, Rigby SEJ, Cliff MJ, Spiess R, Cannas DM, Larrosa I, Hay S, Leys D: Structure and Mechanism of Pseudomonas aeruginosa PA0254/HudA, a prFMN-Dependent Pyrrole-2-carboxylic Acid Decarboxylase Linked to Virulence. ACS Catal. 2021 Mar 5;11(5):2865-2878. doi: 10.1021/acscatal.0c05042. Epub 2021 Feb 17. [PubMed:33763291 ]