ContaminantDB: Pyrrolidonecarboxylic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:22:29 UTC

Update Date

2016-11-09 01:21:13 UTC

Accession Number

CHEM034964

Identification

Common Name

Pyrrolidonecarboxylic acid

Class

Small Molecule

Description

An oxoproline having the oxo group placed at the 5-position. It is an intermediate metabolite in the glutathione cycle.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Pyrrolidone-5-carboxylic acid	ChEBI
5-oxo-DL-Proline	ChEBI
5-Pyrrolidone-2-carboxylic acid	ChEBI
Glp	ChEBI
Pyroglutamate	ChEBI
Pyroglutamic acid	ChEBI
2-Pyrrolidone-5-carboxylate	Generator
5-Pyrrolidone-2-carboxylate	Generator
Pyrrolidonecarboxylate	Generator
(+)-2-Pyrrolidone-5-carboxylate	HMDB
(+)-2-Pyrrolidone-5-carboxylic acid	HMDB
(+)-Pyroglutamate	HMDB
(+)-Pyroglutamic acid	HMDB
(2R)-2-Carboxy-5-pyrrolidinone	HMDB
(R)-(+)-2-Pyrrolidone-5-carboxylate	HMDB
(R)-(+)-2-Pyrrolidone-5-carboxylic acid	HMDB
(R)-2-Pyrrolidone-5-carboxylate	HMDB
(R)-2-Pyrrolidone-5-carboxylic acid	HMDB
(R)-5-Oxopyrrolidine-2-carboxylate	HMDB
(R)-5-Oxopyrrolidine-2-carboxylic acid	HMDB
5-oxo-D-Proline	HMDB
D-2-Pyrrolidone-5-carboxylic	HMDB
D-5-Pyrrolidone-2-carboxylate	HMDB
D-5-Pyrrolidone-2-carboxylic acid	HMDB
D-Pyroglutamate	HMDB
D-Pyroglutamic acid	HMDB
5-Ketoproline	MeSH, HMDB
5-Oxoproline	MeSH, HMDB
Pidolate, magnesium	MeSH, HMDB
Pidolic acid	MeSH, HMDB
5-Oxopyrrolidine-2-carboxylic acid	MeSH, HMDB
Magnesium pidolate	MeSH, HMDB
Pyrrolidonecarboxylic acid	MeSH

Chemical Formula

C₅H₇NO₃

Average Molecular Mass

129.114 g/mol

Monoisotopic Mass

129.043 g/mol

CAS Registry Number

149-87-1

IUPAC Name

5-oxopyrrolidine-2-carboxylic acid

Traditional Name

pyroglutamate

SMILES

OC(=O)N1CCCC1=O

InChI Identifier

InChI=1S/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9)

InChI Key

DQAKJEWZWDQURW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidinemonocarboxylic acid (CHEBI:16010 )
pyrrolidin-2-ones (CHEBI:16010 )
oxoproline (CHEBI:16010 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	151 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.89	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.09 m³·mol⁻¹	ChemAxon
Polarizability	11.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0900000000-b41e3a258706b48b80ad	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-001i-9300000000-b5c23f97f5bd408c2910	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-1910000000-7a4c0287311301949021	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0910000000-7965a220921380301b85	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-b41e3a258706b48b80ad	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-9300000000-b5c23f97f5bd408c2910	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-1910000000-7a4c0287311301949021	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-f14d615c29a3dda06991	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9100000000-0207d9b33e7505df2b17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9600000000-8e7afe6ced148f01b715	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9000000000-21b65f5a05735d8f6916	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a5c-9000000000-87d3859fb9096e75c2a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-11bdcfc4a30eb010684f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-eb1ffde5dba339f1ae8e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-4900000000-08bc0ae8cf0b3809b84e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-c811841958c6567b8e98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9400000000-3e005daef5239c2cecb4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o3-9000000000-a408e85310e25b6fa7b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-c9543eaa9b5579e46ef5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-8900000000-265e5da8155fb3b596be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d7e64b39b411328bbb77	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-6c87253da642bb4800df	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000805

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Pyroglutamic_acid

Chemspider ID

Not Available

ChEBI ID

16010

PubChem Compound ID

499

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23217740

Pyrrolidonecarboxylic acid (CHEM034964)

Structure for CHEM034964: Pyrrolidonecarboxylic acid