Showing Compound Pyrrole-2-carboxylic acid (FDB023340)

Record Information

Version

1.0

Creation date

2011-09-21 00:28:20 UTC

Update date

2015-10-09 22:33:14 UTC

Primary ID

FDB023340

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pyrrole-2-carboxylic acid

Description

Pyrrole-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 Number

634-97-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Pyrrolecarboxylic acid	ChEBI
Minaline	ChEBI
PCA	ChEBI
Pyrrole-2-carboxylate	ChEBI
2-Pyrrolecarboxylate	Generator
1H-Pyrrole-2-carboxylic acid	HMDB
1H-Pyrrole-2-carboxylic acid (9ci)	HMDB
2-Minaline	HMDB
Minalin	HMDB
PYC	HMDB
2-Pyrrolecarboxylic acid, monosodium salt	MeSH, HMDB
Pyrrole-2-carboxylic acid	Generator
1H-Pyrrole-2-carboxylic acid (9CI)	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	164 g/L	ALOGPS
logP	0.7	ALOGPS
logP	0.63	ChemAxon
logS	0.17	ALOGPS
pKa (Strongest Acidic)	5.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.95 m³·mol⁻¹	ChemAxon
Polarizability	10.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H5NO2

IUPAC name

1H-pyrrole-2-carboxylic acid

InChI Identifier

InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)

InChI Key

WRHZVMBBRYBTKZ-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC=CN1

Average Molecular Weight

111.0987

Monoisotopic Molecular Weight

111.032028409

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Pyrrole carboxylic acids and derivatives

Direct Parent

Pyrrole 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrolecarboxylic acid (CHEBI:36751 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Source:

Endogenous

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Pyrrole-2-carboxylic acid, 1 TMS, GC-MS Spectrum	splash10-00di-4900000000-efa4fc1d653090d2d0e4	Spectrum
GC-MS	Pyrrole-2-carboxylic acid, 2 TMS, GC-MS Spectrum	splash10-00kf-2960000000-4cfedbfeebcc464b55cb	Spectrum
GC-MS	Pyrrole-2-carboxylic acid, non-derivatized, GC-MS Spectrum	splash10-00kf-2960000000-4cfedbfeebcc464b55cb	Spectrum
GC-MS	Pyrrole-2-carboxylic acid, non-derivatized, GC-MS Spectrum	splash10-00di-4900000000-efa4fc1d653090d2d0e4	Spectrum
GC-MS	Pyrrole-2-carboxylic acid, non-derivatized, GC-MS Spectrum	splash10-00kg-1930000000-f3284be04e5e8bfeac8b	Spectrum
Predicted GC-MS	Pyrrole-2-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03xu-9200000000-33ab2d86788b7fcdd4c5	Spectrum
Predicted GC-MS	Pyrrole-2-carboxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-8900000000-03fc82d55f34cfc0748c	Spectrum
Predicted GC-MS	Pyrrole-2-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-9100000000-c1b7a81a7ce1be943119	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014l-9000000000-84e967fa699d0cafb578	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-b595715063572edc0dce	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-1900000000-c7372bbc4222328a0fd1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-9000000000-bd5aa8d6918fc5699127	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-9000000000-7adfc180c9cd0187ef50	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-9000000000-26d8fa6604dcce168ace	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014r-9000000000-d02c2068388d3953f43e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-1900000000-c7372bbc4222328a0fd1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-bd5aa8d6918fc5699127	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-7adfc180c9cd0187ef50	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-d947b1d957c2f6581e1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014r-9000000000-d02c2068388d3953f43e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-a2af5bd2aa42260c720f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-f14d9350f9dab98d1209	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f6aeaa6f98bd998f78a4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-9000000000-068e8b4c4ccf0f4dcd92	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4900000000-f6d2c4c13ec24df8abcb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9200000000-c7f0b11c04224c0dced0	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-9800000000-2c170003a8d201c6eca8	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9100000000-6eae79c5cb980732b059	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-71849ef71def20737bc9	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-5900000000-370eb1bf3ec71fa2ef1c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-9400000000-5d37d525e8ded1560ddf	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-5d4ed399bdbd9f14b497	2017-07-26	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum