Livestock Metabolome Database: Showing metabocard for Pyroglutamic acid (LMDB00123)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:51 UTC

Update Date

2016-07-20 20:50:55 UTC

Lmdb

LMDB00123

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyroglutamic acid

Description

Pyroglutamic acid, also known as pyroglutamate or pidolate, 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. Pyroglutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyroglutamic acid exists in all living species, ranging from bacteria to humans. Within humans, pyroglutamic acid participates in a number of enzymatic reactions. In particular, pyroglutamic acid can be converted into L-glutamic acid; which is mediated by the enzyme 5-oxoprolinase. In addition, L-cysteine and pyroglutamic acid can be biosynthesized from γ-glutamylcysteine through the action of the enzyme Gamma-glutamylcyclotransferase. An optically active form of Pyroglutamic acid having L-configuration. In humans, pyroglutamic acid is involved in the metabolic disorder called the 5-oxoprolinase deficiency pathway. Pyroglutamic acid is a mild, sweet, and ethereal tasting compound. Outside of the human body, Pyroglutamic acid is found, on average, in the highest concentration within soy beans and beers. Pyroglutamic acid has also been detected, but not quantified in, several different foods, such as horseradish, nuts, cupuaçus, docks, and cascade huckleberries. This could make pyroglutamic acid a potential biomarker for the consumption of these foods. Pyroglutamic acid is a potentially toxic compound. Pyroglutamic acid, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, supragingival calculus, schizophrenia, and eosinophilic esophagitis; pyroglutamic acid has also been linked to the inborn metabolic disorder glutathione synthetase deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-2-Pyrrolidone-5-carboxylic acid	ChEBI
(S)-(-)-2-Pyrrolidone-5-carboxylic acid	ChEBI
(S)-Pyroglutamic acid	ChEBI
5-Pyrrolidone-2-carboxylic acid	ChEBI
L-5-Pyrrolidone-2-carboxylic acid	ChEBI
L-Pyroglutamic acid	ChEBI
Pidolic acid	ChEBI
Pyroglutamate	ChEBI
5-oxo-L-Proline	Kegg
(-)-2-Pyrrolidone-5-carboxylate	Generator
(S)-(-)-2-Pyrrolidone-5-carboxylate	Generator
(S)-Pyroglutamate	Generator
5-Pyrrolidone-2-carboxylate	Generator
L-5-Pyrrolidone-2-carboxylate	Generator
L-Pyroglutamate	Generator
Pidolate	Generator
(-)-Pyroglutamate	HMDB
(-)-Pyroglutamic acid	HMDB
(5S)-2-Oxopyrrolidine-5-carboxylate	HMDB
(5S)-2-Oxopyrrolidine-5-carboxylic acid	HMDB
(S)-(-)-g-Butyrolactam-g-carboxylate	HMDB
(S)-(-)-g-Butyrolactam-g-carboxylic acid	HMDB
(S)-(-)-gamma-Butyrolactam-gamma-carboxylate	HMDB
(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid	HMDB
(S)-2-Pyrrolidone-5-carboxylate	HMDB
(S)-2-Pyrrolidone-5-carboxylic acid	HMDB
(S)-5-oxo-2-Pyrrolidinecarboxylate	HMDB
(S)-5-oxo-2-Pyrrolidinecarboxylic acid	HMDB
2-L-Pyrrolidone-5-carboxylate	HMDB
2-L-Pyrrolidone-5-carboxylic acid	HMDB
2-Oxopyrrolidine-5(S)-carboxylate	HMDB
2-Oxopyrrolidine-5(S)-carboxylic acid	HMDB
2-Pyrrolidinone-5-carboxylate	HMDB
2-Pyrrolidinone-5-carboxylic acid	HMDB
5-Carboxy-2-pyrrolidinone	HMDB
5-L-Oxoproline	HMDB
5-Oxoproline	HMDB
5-Pyrrolidinone-2-carboxylate	HMDB
5-Pyrrolidinone-2-carboxylic acid	HMDB
Ajidew a 100	HMDB
Glutimate	HMDB
Glutimic acid	HMDB
Glutiminate	HMDB
Glutiminic acid	HMDB
L-2-Pyrrolidone-5-carboxylate	HMDB
L-2-Pyrrolidone-5-carboxylic acid	HMDB
L-5-Carboxy-2-pyrrolidinone	HMDB
L-5-oxo-2-Pyrrolidinecarboxylate	HMDB
L-5-oxo-2-Pyrrolidinecarboxylic acid	HMDB
L-5-Oxoproline	HMDB
L-Glutamic acid g-lactam	HMDB
L-Glutimate	HMDB
L-Glutimic acid	HMDB
L-Glutiminate	HMDB
L-Glutiminic acid	HMDB
L-Pyrrolidinonecarboxylate	HMDB
L-Pyrrolidinonecarboxylic acid	HMDB
L-Pyrrolidonecarboxylate	HMDB
L-Pyrrolidonecarboxylic acid	HMDB
Oxoproline	HMDB
Oxopyrrolidinecarboxylate	HMDB
Oxopyrrolidinecarboxylic acid	HMDB
Pidolidone	HMDB
Pyrrolidinonecarboxylate	HMDB
Pyrrolidinonecarboxylic acid	HMDB
Pyrrolidone-5-carboxylate	HMDB
Pyrrolidone-5-carboxylic acid	HMDB
Pyrrolidonecarboxylic acid	HMDB
5-Ketoproline	HMDB
Pidolate, magnesium	HMDB
5-Oxopyrrolidine-2-carboxylic acid	HMDB
Magnesium pidolate	HMDB
2-Pyrrolidone-5-carboxylic acid	HMDB
5-Oxoprolinate	HMDB
PCA	HMDB

Chemical Formula

C₅H₇NO₃

Average Molecular Weight

129.114

Monoisotopic Molecular Weight

129.042593095

IUPAC Name

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

Traditional Name

pyroglutamic acid

CAS Registry Number

98-79-3

SMILES

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

InChI Identifier

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

InChI Key

ODHCTXKNWHHXJC-VKHMYHEASA-N

Chemical Taxonomy

Description

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
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Pyrroline
Cyclic carboximidic acid
Lactim
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:18183 )
L-proline derivative (CHEBI:18183 )
5-oxoproline (CHEBI:18183 )
Other amino acids (C01879 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1	ALOGPS
logP	-0.89	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-2.2	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	11.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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) (2 TMS)	splash10-0ab9-8900000000-f79dc90370ba38f587c9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ab9-8900000000-f79dc90370ba38f587c9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-90fb43273551aeb9b2c4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-130a8f31f82e83c4be07	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9200000000-d69b52257404ab658d5b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9500000000-ebc64308ec5d5bdb303e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9000000000-7377cb17491942e9589c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053u-9000000000-fcab1396867356ebd6ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-5b0c6536e1b3217b8544	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-c30ac0bd264c8007ef92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-5900000000-ea3a164653e4235716ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0f89-9000000000-f6620738e68f990d0594	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-7937bee2e9a6d6b29cbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-f20401903b234914b936	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-9446bb65e0edd72cfd59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-7900000000-74eccdeb9f0d5fd17614	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0f8a-9000000000-8786a9cd5e488192f34d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0f6t-9000000000-ebcc1ac4acd525218e80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-01q9-2900000000-754ae9b699ec1b22cd76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9300000000-eabb8c4dc0d1111e0431	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00lr-9100000000-1dd17702aee7e5bce618	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-067i-9000000000-c9669794d3a8746be498	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-9e103abb0a6ed890051e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03e9-3900000000-da8cf252285c1d616586	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-01q9-9400000000-96a7fe5a81188c49d1ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014i-9000000000-356215339a43217dea66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-02vl-9000000000-ed47ec6e675eb338da19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-f647da344adbdf7bfb1b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9200000000-0bddc68d58c6fb981d1a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-0900000000-c70c79fa828bbf137ebc	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-6c87253da642bb4800df	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Cerebrospinal Fluid (CSF)
Feces
Milk
Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Applicable	Not Available	Ovine	17510975	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	356 +/- 45 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	356 +/- 45 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	384 +/- 59 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	486 +/- 94 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	525 +/- 120 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Ruminal Fluid	Detected and Quantified	355.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	384.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	486.8 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	524.7 uM	Not Available	Bovine	22959937	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details