Milk Composition Database: Showing metabocard for Pyroglutamic acid (BMDB0000267)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:37 UTC

Update Date

2020-06-04 20:58:01 UTC

MCDB ID

BMDB0000267

Secondary Accession Numbers

BMDB00267

Metabolite Identification

Common Name

Pyroglutamic acid

Description

Pyroglutamic acid, also known as pyroglutamate or pidolate, magnesium, 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 possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pyroglutamic acid exists in all living species, ranging from bacteria to humans. Pyroglutamic acid is a potentially toxic compound.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	476 mg/mL at 13 °C	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	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	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)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details

External Links

HMDB ID

HMDB0000267

DrugBank ID

DB03088

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Pumpor, Ksenia; Boettcher, Christoph; Fehn, Susanna; Burger, Klaus. Hexafluoroacetone as protecting and activating reagent: an efficient strategy for activation of pyroglutamic acid and homologs.Heterocycles (2003), 61 259-269.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]
Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

Showing metabocard for Pyroglutamic acid (BMDB0000267)

Structure for BMDB0000267 (Pyroglutamic acid)