MiMeDB: Showing metabocard for Pyroglutamic acid (MMDBc0000509)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:23 UTC

Update Date

2024-10-10 00:24:57 UTC

Metabolite ID

MMDBc0000509

Metabolite Identification

Common Name

Pyroglutamic acid

Description

Pyroglutamic acid (5-oxoproline) is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissues in bound form, especially skin. It is also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain. Pyroglutamate in the urine is a biomarker for the consumption of cheese. When present in sufficiently high levels, pyroglutamic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyroglutamic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria, 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia. Pyroglutamic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. It has been shown that pyroglutamic acid releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, pyroglutamic acid significantly shortens the plasma half-life of ethanol during acute intoxication.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

Molecular Formula

C₅H₇NO₃

Average Mass

129.114

Monoisotopic Mass

129.042593095

IUPAC Name

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

Traditional Name

pyroglutamic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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)	-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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ab9-8900000000-f79dc90370ba38f587c9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-90fb43273551aeb9b2c4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-130a8f31f82e83c4be07	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9200000000-d69b52257404ab658d5b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9500000000-ebc64308ec5d5bdb303e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9000000000-7377cb17491942e9589c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053u-9000000000-fcab1396867356ebd6ae	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-5b0c6536e1b3217b8544	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-c30ac0bd264c8007ef92	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-5900000000-ea3a164653e4235716ae	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0f89-9000000000-f6620738e68f990d0594	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-7937bee2e9a6d6b29cbd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-f20401903b234914b936	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-9446bb65e0edd72cfd59	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-7900000000-74eccdeb9f0d5fd17614	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0f8a-9000000000-8786a9cd5e488192f34d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0f6t-9000000000-ebcc1ac4acd525218e80	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-01q9-2900000000-754ae9b699ec1b22cd76	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9300000000-eabb8c4dc0d1111e0431	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00lr-9100000000-1dd17702aee7e5bce618	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-067i-9000000000-c9669794d3a8746be498	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-9e103abb0a6ed890051e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03e9-3900000000-da8cf252285c1d616586	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-01q9-9400000000-96a7fe5a81188c49d1ba	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014i-9000000000-356215339a43217dea66	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-02vl-9000000000-ed47ec6e675eb338da19	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-f647da344adbdf7bfb1b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9200000000-0bddc68d58c6fb981d1a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-0900000000-c70c79fa828bbf137ebc	2012-08-31	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-6c87253da642bb4800df	2019-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Placenta
Prostate
Saliva
Sweat
Urine

Tissue Locations

Brain
Epidermis
Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192331	Glutaminyl-peptide cyclotransferase	Unknown	Q16769	Homo sapiens
MMDBp0192475	5-oxoprolinase	Enzyme	O14841	Homo sapiens
MMDBp0193278	Angiogenin	Enzyme	P03950	Homo sapiens
MMDBp0193290	Ig lambda chain V-II region MGC	Enzyme	P01709	Homo sapiens
MMDBp0193413	Alpha-amylase 1	Unknown	P04745	Homo sapiens
MMDBp0193414	Pancreatic alpha-amylase	Unknown	P04746	Homo sapiens
MMDBp0193427	Vascular endothelial growth factor A	Enzyme	P15692	Homo sapiens
MMDBp0193433	Alpha-amylase 2B	Unknown	P19961	Homo sapiens
MMDBp0193503	Orexin	Enzyme	O43612	Homo sapiens
MMDBp0196046	Gamma-glutamylcyclotransferase	Enzyme	O75223	Homo sapiens
MMDBp0196646	Ig lambda-1 chain C regions	Enzyme	P0CG04	Homo sapiens
MMDBp0196817	Gamma-glutamylaminecyclotransferase	Unknown	Q9BVM4

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001300	gamma-Glutamylalanine	Pyroglutamic acid	gamma-glutamylcyclotransferase	VMH	2570694
MMDBr0001828	Pyroglutamic acid	L-Glutamic acid	Not Available	VMH	9751079
MMDBr0002603	gamma-Glutamylcysteine	Pyroglutamic acid	gamma-glutamylcyclotransferase	VMH; KEGG	30371894
MMDBr0004153	Gama-L-Glutamyl-L-Alpha-Aminobutyrate	Pyroglutamic acid	Not Available	VMH	2570694 6150932
MMDBr0004154	Gama-Glutamylglutathione	Pyroglutamic acid	Not Available	VMH	2570694 6150932
MMDBr0004223	Thyrotropin Releasing Hormone	Pyroglutamic acid	thyrotropin-releasing hormone degrading enzyme	VMH	10491199

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	132	Human stool; Human ; Human feces; Pig ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	28	Human ; Human feces; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	203	Human feces; Human sputum; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	15	Human feces; Human appendix biopsy; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Fusobacteria	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4	Human feces; Human saliva	Unknown
Bacteria	Chloroflexi	3
Bacteria	Deinococcus-thermus	3
Archaea/Archaea	Euryarchaeota	6		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Leaves	Psidium guajava	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	5570				umol/mmol creatinine	Children (1-13 years old)	Not Specified	5-Oxoprolinase Deficiency	HMDB	25129617
Human Urine	Detected and Quantified			1980	6040	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	5-Oxoprolinase Deficiency	HMDB	10094443
Human Urine	Detected and Quantified			137.6	4092.79	umol/mmol creatinine	Children (1 - 13 years old)	Both	Glutathione synthetase deficiency	HMDB	25851806
Human Sweat	Detected and Quantified	< 10				uM	Adult (60 years old)	Male	Normal	HMDB	22194922
Human Sweat	Detected and Quantified	< 10				uM	Adult (40 years old)	Male	Normal	HMDB	22194922
Human Urine	Detected and Quantified	<10				umol/mmol creatinine	Not Specified	Not Specified	Normal	HMDB	23430506
Human Urine	Detected and Quantified	<7.6				umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	25851806
Human Urine	Detected and Quantified	14.0	7.2			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15992788
Human Urine	Detected and Quantified			17	25	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	18.6		4.5	24.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	19.5	3.7			uM	Adult (>18 years old)	Both	Normal	HMDB	18029477
Human Urine	Detected and Quantified	20.7		10.2	32.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			21	30	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	24.1		3.4	54.2	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	3.1		1.9	11.3	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Cerebrospinal fluid (csf)	Detected and Quantified	41.0	31.0			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8412012
Human Cerebrospinal fluid (csf)	Detected and Quantified	47	30			uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Urine	Detected and Quantified			5	12.3	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			5	44	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Urine	Detected and Quantified	5.3		2.9	10.4	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified			6.0	22.2	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			6.7	27.1	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified	7.3		0.1	29.3	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified			8.6	22.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified	34.75	17.53			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	47.522	35.017			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	28.8		3.4	54.2	umol/mmol creatinine	Adult (>18 years old)	Both	5-oxoprolinase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	3500.0		1000.0	6000.0	umol/mmol creatinine	Children (1-13 years old)	Both	5-Oxoprolinase Deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	3.5		3.00	4.00	uM	Children (1-13 years old)	Both	Glutathione synthetase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	87.00		13.00	161.00	uM	Adult (>18 years old)	Both	Glutathione synthetase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	40.428	19.331			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	47.641	19.524			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	<79.14				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Saliva	Detected and Quantified	0.618	0.758			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	15.0	32.5			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	18.2	20.9			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	3.82	5.16			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	3.84	2.81			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	5.65	4.71			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	8.70	7.55			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	30.19	31.32			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21330412
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	22944170
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22024767
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22024767
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28842642
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000267

DrugBank ID

DB03088

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014506

KNApSAcK ID

C00007403

Chemspider ID

Not Available

KEGG Compound ID

C01879

BioCyc ID

5-OXOPROLINE

BiGG ID

Not Available

Wikipedia Link

Pyroglutamic_acid

METLIN ID

Not Available

PubChem Compound

7405

PDB ID

Not Available

ChEBI ID

18183

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Palekar AG, Tate SS, Sullivan JF, Meister A: Accumulation of 50oxo-L-proline and 5-oxo-D-proline in the blood plasma in end stage renal disease. Biochem Med. 1975 Nov;14(3):339-45. doi: 10.1016/0006-2944(75)90052-6. [PubMed:1225334 ]
Winslow JW, Shih A, Bourell JH, Weiss G, Reed B, Stults JT, Goldsmith LT: Human seminal relaxin is a product of the same gene as human luteal relaxin. Endocrinology. 1992 May;130(5):2660-8. doi: 10.1210/endo.130.5.1572287. [PubMed:1572287 ]
Hammond JW, Potter M, Truscott R, Wilcken B: gamma-Glutamylglutamine identified in plasma and cerebrospinal fluid from hyperammonaemic patients. Clin Chim Acta. 1990 Dec 24;194(2-3):173-83. doi: 10.1016/0009-8981(90)90132-c. [PubMed:2093471 ]
Creer MH, Lau BW, Jones JD, Chan KM: Pyroglutamic acidemia in an adult patient. Clin Chem. 1989 Apr;35(4):684-6. [PubMed:2702756 ]
Uhlhaas S, Lange H: Striatal deficiency of L-pyroglutamic acid in Huntington's disease is accompanied by increased plasma levels. Brain Res. 1988 Aug 2;457(1):196-9. doi: 10.1016/0006-8993(88)90076-5. [PubMed:2971422 ]
Jellum E, Stokke O, Eldjarn L: Combined use of gas chromatography, mass spectrometry, and computer in diagnosis and studies of metabolic disorders. Clin Chem. 1972 Aug;18(8):800-9. [PubMed:4557757 ]
Hussain Z, Lannigan R, Stoakes L: A new approach for presumptive identification of clinically important streptococci. Zentralbl Bakteriol Mikrobiol Hyg A. 1984 Oct;258(1):74-9. doi: 10.1016/s0176-6724(84)80011-5. [PubMed:6441390 ]
Manning NJ, Davies NP, Olpin SE, Carpenter KH, Smith MF, Pollitt RJ, Duncan SL, Larsson A, Carlsson B: Prenatal diagnosis of glutathione synthase deficiency. Prenat Diagn. 1994 Jun;14(6):475-8. doi: 10.1002/pd.1970140611. [PubMed:7937585 ]
Wevers RA, Engelke U, Heerschap A: High-resolution 1H-NMR spectroscopy of blood plasma for metabolic studies. Clin Chem. 1994 Jul;40(7 Pt 1):1245-50. [PubMed:8013094 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Erasmus E, Mienie LJ, de Vries WN, de Wet WJ, Carlsson B, Larsson A: Prenatal analysis in two suspected cases of glutathione synthetase deficiency. J Inherit Metab Dis. 1993;16(5):837-43. doi: 10.1007/BF00714275. [PubMed:8295398 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. doi: 10.1007/BF00711898. [PubMed:8412012 ]
Croal BL, Glen AC, Kelly CJ, Logan RW: Transient 5-oxoprolinuria (pyroglutamic aciduria) with systemic acidosis in an adult receiving antibiotic therapy. Clin Chem. 1998 Feb;44(2):336-40. [PubMed:9474033 ]
Caspers PJ, Lucassen GW, Carter EA, Bruining HA, Puppels GJ: In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles. J Invest Dermatol. 2001 Mar;116(3):434-42. doi: 10.1046/j.1523-1747.2001.01258.x. [PubMed:11231318 ]
Monsigny M, Rondanino C, Duverger E, Fajac I, Roche AC: Glyco-dependent nuclear import of glycoproteins, glycoplexes and glycosylated plasmids. Biochim Biophys Acta. 2004 Jul 6;1673(1-2):94-103. doi: 10.1016/j.bbagen.2004.03.015. [PubMed:15238252 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Pyroglutamic acid (MMDBc0000509)

MOL for #<Metabolite:0x00007f46c2d61680>

3D MOL for #<Metabolite:0x00007f46c2d61680>

3D SDF for #<Metabolite:0x00007f46c2d61680>

3D-SDF for #<Metabolite:0x00007f46c2d61680>

PDB for #<Metabolite:0x00007f46c2d61680>

3D PDB for #<Metabolite:0x00007f46c2d61680>

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Structure for #<Metabolite:0x00007f46c2d61680>

3D Structure for #<Metabolite:0x00007f46c2d61680>