P. aeruginosa Metabolome Database: Pyrrolidonecarboxylic acid (PAMDB000187)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000187

Identification

Name:

Pyrrolidonecarboxylic acid

Description:

Pyrrolidonecarboxylic acid is a member of the chemical class known as Pyrrolidine Carboxylic Acids and Derivatives. These are compounds containing a pyrrolidine ring which bears a carboxylic acid or a derivative thereof. 2-Pyrrolidone-5-carboxylic acid (PCA) is a cyclic derivative of glutamic acid, and has been found in Pseudomonas aeruginosa beta-galactosidase. It is produced by gamma-glutamyl phosphate reductase (glutamate semialdehyde dehydrogenase) via glutamic acid 5-semidaldehyde [PMID: 7034716].

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(+)-2-Pyrrolidone-5-carboxylate
(+)-2-Pyrrolidone-5-carboxylic acid
(+)-Pyroglutamate
(+)-Pyroglutamic acid
(2R)-2-Carboxy-5-pyrrolidinone
(R)-(+)-2-Pyrrolidone-5-carboxylate
(R)-(+)-2-Pyrrolidone-5-carboxylic acid
(R)-2-Pyrrolidone-5-carboxylate
(R)-2-Pyrrolidone-5-carboxylic acid
(R)-5-Oxopyrrolidine-2-carboxylate
(R)-5-Oxopyrrolidine-2-carboxylic acid
5-Oxo-D-proline
D-2-Pyrrolidone-5-carboxylic
D-5-Pyrrolidone-2-carboxylate
D-5-Pyrrolidone-2-carboxylic acid
D-Pyroglutamate
D-Pyroglutamic acid
Pyrrolidonecarboxylate

Chemical Formula:

C₅H₇NO₃

Average Molecular Weight:

129.114

Monoisotopic Molecular Weight:

129.042593095

InChI Key:

ODHCTXKNWHHXJC-VKHMYHEASA-N

InChI:

InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1

CAS number:

4042-36-8

IUPAC Name:

(2R)-5-oxopyrrolidine-2-carboxylic acid

Traditional IUPAC Name:

5-oxo-D-proline

SMILES:

OC(=O)[C@@H]1CCC(=O)N1

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Oxoproline
2-pyrrolidone
Pyrrolidone
Pyrrolidine
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid amide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

5-oxoproline (CHEBI:16924 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

155 - 162 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	Soluble	PhysProp
LogP:	-0.809	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	151.0 mg/mL	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	11.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

D-Glutamine and D-glutamate metabolism pae00471

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-c811841958c6567b8e98	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9400000000-3e005daef5239c2cecb4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o3-9000000000-a408e85310e25b6fa7b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-c9543eaa9b5579e46ef5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-8900000000-265e5da8155fb3b596be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d7e64b39b411328bbb77	View in MoNA

References

References:

Hayzer, D. J., Leisinger, T. (1981). "Proline biosynthesis in Escherichia coli. Stoichiometry and end-product identification of the reaction catalysed by glutamate semialdehyde dehydrogenase." Biochem J 197:269-274. Pubmed: 7034716
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16924
HMDB ID	HMDB00805
Pubchem Compound ID	439685
Kegg ID	C02237
ChemSpider ID	388752
Wikipedia ID	Not Available
BioCyc ID	CPD-656
EcoCyc ID	CPD-656

Pyrrolidonecarboxylic acid (PAMDB000187)

Structure for Pyrrolidonecarboxylic acid (PAMDB000187)