Pyroglutamic acid (YMDB00107)

Identification

YMDB ID

YMDB00107

Name

Pyroglutamic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

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. Pyroglutamic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-2-Pyrrolidone-5-carboxylate
(-)-2-Pyrrolidone-5-carboxylic acid
(-)-Pyroglutamate
(-)-Pyroglutamic acid
(5S)-2-Oxopyrrolidine-5-carboxylate
(5S)-2-Oxopyrrolidine-5-carboxylic acid
(S)-(-)-2-Pyrrolidone-5-carboxylate
(S)-(-)-2-Pyrrolidone-5-carboxylic acid
(S)-(-)-g-Butyrolactam-g-carboxylate
(S)-(-)-g-Butyrolactam-g-carboxylic acid
(S)-(-)-gamma-Butyrolactam-gamma-carboxylate
(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid
(S)-2-Pyrrolidone-5-carboxylate
(S)-2-Pyrrolidone-5-carboxylic acid
(S)-5-Oxo-2-pyrrolidinecarboxylate
(S)-5-Oxo-2-pyrrolidinecarboxylic acid
(S)-Pyroglutamate
(S)-Pyroglutamic acid
2-L-Pyrrolidone-5-carboxylate
2-L-Pyrrolidone-5-carboxylic acid
2-Oxopyrrolidine-5(S)-carboxylate
2-Oxopyrrolidine-5(S)-carboxylic acid
2-Pyrrolidinone-5-carboxylate
2-Pyrrolidinone-5-carboxylic acid
5-Carboxy-2-pyrrolidinone
5-L-oxoproline
5-Oxo-L-proline
5-Oxoproline
5-Pyrrolidinone-2-carboxylate
5-Pyrrolidinone-2-carboxylic acid
Glutimate
Glutimic acid
Glutiminate
Glutiminic acid
L-2-Pyrrolidone-5-carboxylate
L-2-Pyrrolidone-5-carboxylic acid
L-5-Carboxy-2-pyrrolidinone
L-5-Oxo-2-pyrrolidinecarboxylate
L-5-Oxo-2-pyrrolidinecarboxylic acid
L-5-Oxoproline
L-Glutamic acid g-lactam
L-Glutimate
L-Glutimic acid
L-Glutiminate
L-Glutiminic acid
L-Pyroglutamate
L-Pyroglutamic acid
L-Pyrrolidinonecarboxylate
L-Pyrrolidinonecarboxylic acid
L-Pyrrolidonecarboxylate
L-Pyrrolidonecarboxylic acid
Oxoproline
Oxopyrrolidinecarboxylate
Oxopyrrolidinecarboxylic acid
Pidolate
Pidolic acid
Pidolidone
Pyroglutamate
Pyroglutamic acid
Pyrrolidinonecarboxylate
Pyrrolidinonecarboxylic acid
Pyrrolidone-5-carboxylate
Pyrrolidone-5-carboxylic acid
Pyrrolidonecarboxylic acid
5-Pyrrolidone-2-carboxylic acid
L-5-Pyrrolidone-2-carboxylic acid
5-Pyrrolidone-2-carboxylate
L-5-Pyrrolidone-2-carboxylate
Ajidew a 100
5-Ketoproline
Pidolate, magnesium
5-Oxopyrrolidine-2-carboxylic acid
Magnesium pidolate
2-Pyrrolidone-5-carboxylic acid
5-Oxoprolinate
PCA

CAS number

98-79-3

Weight

Average: 129.114
Monoisotopic: 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

IUPAC Name

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

Traditional IUPAC Name

pyroglutamic acid

Chemical Formula

C₅H₇NO₃

SMILES

[H]OC(=O)[C@@]1([H])N([H])C(=O)C([H])([H])C1([H])[H]

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

Charge

Melting point

184.7 °C

Experimental Properties

Property	Value	Reference
Water Solubility	476 mg/mL at 13 oC [BEILSTEIN]	PhysProp
LogP	Not Available	PhysProp

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	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

Organoleptic Properties

Flavour/Odour	Source
Ethereal	FDB014506
Mild	FDB014506
Sweet	FDB014506

SMPDB Pathways

Glutathione metabolism

PW002395

KEGG Pathways

Glutathione metabolism

ec00480

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

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	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ab9-8900000000-f79dc90370ba38f587c9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-90fb43273551aeb9b2c4	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-130a8f31f82e83c4be07	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9200000000-d69b52257404ab658d5b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9500000000-ebc64308ec5d5bdb303e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9000000000-7377cb17491942e9589c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053u-9000000000-fcab1396867356ebd6ae	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-5b0c6536e1b3217b8544	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-c30ac0bd264c8007ef92	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-5900000000-ea3a164653e4235716ae	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0f89-9000000000-f6620738e68f990d0594	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-7937bee2e9a6d6b29cbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-f20401903b234914b936	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-9446bb65e0edd72cfd59	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-7900000000-74eccdeb9f0d5fd17614	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0f8a-9000000000-8786a9cd5e488192f34d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0f6t-9000000000-ebcc1ac4acd525218e80	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-01q9-2900000000-754ae9b699ec1b22cd76	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9300000000-eabb8c4dc0d1111e0431	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00lr-9100000000-1dd17702aee7e5bce618	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-067i-9000000000-c9669794d3a8746be498	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-9e103abb0a6ed890051e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03e9-3900000000-da8cf252285c1d616586	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-01q9-9400000000-96a7fe5a81188c49d1ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014i-9000000000-356215339a43217dea66	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-02vl-9000000000-ed47ec6e675eb338da19	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-f647da344adbdf7bfb1b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9200000000-0bddc68d58c6fb981d1a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-0900000000-c70c79fa828bbf137ebc	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-6c87253da642bb4800df	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339

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.

External Links:

Resource	Link
CHEBI ID	18183
HMDB ID	HMDB00267
Pubchem Compound ID	7405
Kegg ID	C01879
ChemSpider ID	7127
FOODB ID	FDB014506
Wikipedia	Pyroglutamic_acid
BioCyc ID	CPD-589

Enzymes

Protein Details

1. Uncharacterized protein YKL215C

General function:: Involved in hydrolase activity
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: P28273
Molecular weight:: 140426.0

Reactions

ATP + 5-oxo-L-proline + 2 H(2)O → ADP + phosphate + L-glutamate.

Structure for #<Compound:0xadf0a91c>

Enzymes

Reactions