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Showing metabocard for Pyroglutamic acid (HMDB0000267)

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enzymes (12) Show 12 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:58 UTC
HMDB IDHMDB0000267
Secondary Accession Numbers
  • HMDB0000805
  • HMDB00267
  • HMDB0060262
  • HMDB00805
  • HMDB60262
Metabolite Identification
Common NamePyroglutamic acid
DescriptionPyroglutamic 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
Data?1676999680
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000267 (Pyroglutamic acid)

       
  Mrv1652309032023592D          

  9  9  0  0  1  0            999 V2000
   13.9994   -9.9706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6668  -10.4556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3319  -10.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9994   -9.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119  -11.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5869  -11.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2849   -8.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7139   -8.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8968  -11.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0000267 (Pyroglutamic acid)

HMDB0000267
     RDKit          3D
Pyroglutamic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.3404    1.3611   -1.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603    0.7498   -0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -0.7260   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -0.8226    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129    0.3582    0.5930 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6205    0.0916   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8589    0.6985   -1.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496   -0.8456    0.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011    1.3706   -0.0424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.2004   -1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3162   -1.2187   -0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -1.7775    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999   -0.6417    1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.7449    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -0.5291    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    2.3866    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9  2  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  1
  8 15  1  0
  9 16  1  0
M  END
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3D SDF for HMDB0000267 (Pyroglutamic acid)

       
  Mrv1652309032023592D          

  9  9  0  0  1  0            999 V2000
   13.9994   -9.9706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6668  -10.4556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3319  -10.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9994   -9.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119  -11.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5869  -11.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2849   -8.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7139   -8.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8968  -11.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000267

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C5H7NO3

> <MOLECULAR_WEIGHT>
129.114

> <EXACT_MASS>
129.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.55635110215903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-oxopyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.01

> <JCHEM_LOGP>
-0.8896697023333333

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.760445138872075

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.613354339229633

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2244398721602403

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
28.0878

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyroglutamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000267 (Pyroglutamic acid)

HMDB0000267
     RDKit          3D
Pyroglutamic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.3404    1.3611   -1.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603    0.7498   -0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -0.7260   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -0.8226    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129    0.3582    0.5930 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6205    0.0916   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8589    0.6985   -1.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496   -0.8456    0.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011    1.3706   -0.0424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.2004   -1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3162   -1.2187   -0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -1.7775    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999   -0.6417    1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.7449    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -0.5291    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    2.3866    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9  2  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  1
  8 15  1  0
  9 16  1  0
M  END
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PDB for HMDB0000267 (Pyroglutamic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      26.132 -18.612   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      27.378 -19.517   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      24.886 -19.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.132 -17.072   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.902 -20.982   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.362 -20.982   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.798 -16.302   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      27.466 -16.302   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      27.807 -22.228   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9    6                                                  
CONECT    6    3    5                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0000267 (Pyroglutamic acid)

COMPND    HMDB0000267
HETATM    1  O1  UNL     1      -2.340   1.361  -1.402  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.460   0.750  -0.749  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.332  -0.726  -0.573  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.519  -0.823   0.688  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.413   0.358   0.593  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.620   0.092  -0.187  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.859   0.699  -1.261  1.00  0.00           O  
HETATM    8  O3  UNL     1       2.550  -0.846   0.234  1.00  0.00           O  
HETATM    9  N1  UNL     1      -0.401   1.371  -0.042  1.00  0.00           N  
HETATM   10  H1  UNL     1      -0.806  -1.200  -1.426  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.316  -1.219  -0.426  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.005  -1.777   0.812  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.200  -0.642   1.543  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.688   0.745   1.608  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.467  -0.529   0.561  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.217   2.387   0.024  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    9
CONECT    3    4   10   11
CONECT    4    5   12   13
CONECT    5    6    9   14
CONECT    6    7    7    8
CONECT    8   15
CONECT    9   16
END
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SMILES for HMDB0000267 (Pyroglutamic acid)

OC(=O)[C@@H]1CCC(=O)N1
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INCHI for HMDB0000267 (Pyroglutamic acid)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(-)-2-Pyrrolidone-5-carboxylic acidChEBI
(S)-(-)-2-Pyrrolidone-5-carboxylic acidChEBI
(S)-Pyroglutamic acidChEBI
5-Pyrrolidone-2-carboxylic acidChEBI
L-5-Pyrrolidone-2-carboxylic acidChEBI
L-Pyroglutamic acidChEBI
Pidolic acidChEBI
PyroglutamateChEBI
5-oxo-L-ProlineKegg
(-)-2-Pyrrolidone-5-carboxylateGenerator
(S)-(-)-2-Pyrrolidone-5-carboxylateGenerator
(S)-PyroglutamateGenerator
5-Pyrrolidone-2-carboxylateGenerator
L-5-Pyrrolidone-2-carboxylateGenerator
L-PyroglutamateGenerator
PidolateGenerator
(-)-PyroglutamateHMDB
(-)-Pyroglutamic acidHMDB
(5S)-2-Oxopyrrolidine-5-carboxylateHMDB
(5S)-2-Oxopyrrolidine-5-carboxylic acidHMDB
(S)-(-)-g-Butyrolactam-g-carboxylateHMDB
(S)-(-)-g-Butyrolactam-g-carboxylic acidHMDB
(S)-(-)-gamma-Butyrolactam-gamma-carboxylateHMDB
(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acidHMDB
(S)-2-Pyrrolidone-5-carboxylateHMDB
(S)-2-Pyrrolidone-5-carboxylic acidHMDB
(S)-5-oxo-2-PyrrolidinecarboxylateHMDB
(S)-5-oxo-2-Pyrrolidinecarboxylic acidHMDB
2-L-Pyrrolidone-5-carboxylateHMDB
2-L-Pyrrolidone-5-carboxylic acidHMDB
2-Oxopyrrolidine-5(S)-carboxylateHMDB
2-Oxopyrrolidine-5(S)-carboxylic acidHMDB
2-Pyrrolidinone-5-carboxylateHMDB
2-Pyrrolidinone-5-carboxylic acidHMDB
5-Carboxy-2-pyrrolidinoneHMDB
5-L-OxoprolineHMDB
5-OxoprolineHMDB
5-Pyrrolidinone-2-carboxylateHMDB
5-Pyrrolidinone-2-carboxylic acidHMDB
Ajidew a 100HMDB
GlutimateHMDB
Glutimic acidHMDB
GlutiminateHMDB
Glutiminic acidHMDB
L-2-Pyrrolidone-5-carboxylateHMDB
L-2-Pyrrolidone-5-carboxylic acidHMDB
L-5-Carboxy-2-pyrrolidinoneHMDB
L-5-oxo-2-PyrrolidinecarboxylateHMDB
L-5-oxo-2-Pyrrolidinecarboxylic acidHMDB
L-5-OxoprolineHMDB
L-Glutamic acid g-lactamHMDB
L-GlutimateHMDB
L-Glutimic acidHMDB
L-GlutiminateHMDB
L-Glutiminic acidHMDB
L-PyrrolidinonecarboxylateHMDB
L-Pyrrolidinonecarboxylic acidHMDB
L-PyrrolidonecarboxylateHMDB
L-Pyrrolidonecarboxylic acidHMDB
OxoprolineHMDB
OxopyrrolidinecarboxylateHMDB
Oxopyrrolidinecarboxylic acidHMDB
PidolidoneHMDB
PyrrolidinonecarboxylateHMDB
Pyrrolidinonecarboxylic acidHMDB
Pyrrolidone-5-carboxylateHMDB
Pyrrolidone-5-carboxylic acidHMDB
Pyrrolidonecarboxylic acidHMDB
5-KetoprolineHMDB
Pidolate, magnesiumHMDB
5-Oxopyrrolidine-2-carboxylic acidHMDB
Magnesium pidolateHMDB
2-Pyrrolidone-5-carboxylic acidHMDB
5-OxoprolinateHMDB
PCAHMDB
Chemical FormulaC5H7NO3
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
IUPAC Name(2S)-5-oxopyrrolidine-2-carboxylic acid
Traditional Namepyroglutamic acid
CAS Registry Number98-79-3
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 KeyODHCTXKNWHHXJC-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility476 mg/mL at 13 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available124.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000085
[M+H]+Not Available130.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000085
Predicted Molecular Properties
PropertyValueSource
Water Solubility151 g/LALOGPS
logP-1ALOGPS
logP-0.89ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.09 m³·mol⁻¹ChemAxon
Polarizability11.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.07331661259
DarkChem[M-H]-122.92131661259
AllCCS[M+H]+128.68232859911
AllCCS[M-H]-122.92432859911
DeepCCS[M+H]+124.28730932474
DeepCCS[M-H]-121.37930932474
DeepCCS[M-2H]-158.07330932474
DeepCCS[M+Na]+133.15830932474
AllCCS[M+H]+128.732859911
AllCCS[M+H-H2O]+124.132859911
AllCCS[M+NH4]+133.032859911
AllCCS[M+Na]+134.232859911
AllCCS[M-H]-122.932859911
AllCCS[M+Na-2H]-125.032859911
AllCCS[M+HCOO]-127.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pyroglutamic acidOC(=O)[C@@H]1CCC(=O)N12357.5Standard polar33892256
Pyroglutamic acidOC(=O)[C@@H]1CCC(=O)N11245.7Standard non polar33892256
Pyroglutamic acidOC(=O)[C@@H]1CCC(=O)N11724.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyroglutamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N11478.9Semi standard non polar33892256
Pyroglutamic acid,1TMS,isomer #2C[Si](C)(C)N1C(=O)CC[C@H]1C(=O)O1484.5Semi standard non polar33892256
Pyroglutamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C1494.7Semi standard non polar33892256
Pyroglutamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C1478.9Standard non polar33892256
Pyroglutamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C1803.4Standard polar33892256
Pyroglutamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N11718.7Semi standard non polar33892256
Pyroglutamic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)CC[C@H]1C(=O)O1717.9Semi standard non polar33892256
Pyroglutamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C1928.0Semi standard non polar33892256
Pyroglutamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C1945.3Standard non polar33892256
Pyroglutamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C1985.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pyroglutamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0ab9-8900000000-f79dc90370ba38f587c92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyroglutamic acid GC-EI-TOF (Non-derivatized)splash10-0ab9-8900000000-f79dc90370ba38f587c92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyroglutamic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-90fb43273551aeb9b2c42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyroglutamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-130a8f31f82e83c4be072016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyroglutamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9200000000-d69b52257404ab658d5b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyroglutamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyroglutamic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyroglutamic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyroglutamic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-6c87253da642bb4800df2019-05-16Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-9500000000-ebc64308ec5d5bdb303e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-053r-9000000000-7377cb17491942e9589c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-053u-9000000000-fcab1396867356ebd6ae2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-0900000000-5b0c6536e1b3217b85442012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-004i-0900000000-c30ac0bd264c8007ef922012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-004i-5900000000-ea3a164653e4235716ae2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0f89-9000000000-f6620738e68f990d05942012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0udi-9000000000-7937bee2e9a6d6b29cbd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-0900000000-f20401903b234914b9362012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-004i-0900000000-9446bb65e0edd72cfd592012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0059-7900000000-74eccdeb9f0d5fd176142012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0f8a-9000000000-8786a9cd5e488192f34d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0f6t-9000000000-ebcc1ac4acd525218e802012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-01q9-2900000000-754ae9b699ec1b22cd762012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-001i-9300000000-eabb8c4dc0d1111e04312012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00lr-9100000000-1dd17702aee7e5bce6182012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-067i-9000000000-c9669794d3a8746be4982012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-9000000000-9e103abb0a6ed890051e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-03e9-3900000000-da8cf252285c1d6165862012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-01q9-9400000000-96a7fe5a81188c49d1ba2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-014i-9000000000-356215339a43217dea662012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-02vl-9000000000-ed47ec6e675eb338da192012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-9000000000-f647da344adbdf7bfb1b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-001i-9200000000-0bddc68d58c6fb981d1a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyroglutamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-004i-0900000000-c70c79fa828bbf137ebc2012-08-31HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified19.5 +/- 3.7 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified47 +/- 30 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified41.0 +/- 31.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SalivaDetected and Quantified5.65 +/- 4.71 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified8.70 +/- 7.55 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified15.0 +/- 32.5 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified18.2 +/- 20.9 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified3.82 +/- 5.16 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified3.84 +/- 2.81 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.618 +/- 0.758 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified30.19 +/- 31.32 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal		 details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal		 details
UrineDetected and Quantified47.641 +/- 19.524 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<10 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified5-12.3 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified6.0-22.2 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified6.7-27.1 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified8.6-22.0 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified40.428 +/- 19.331 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified21-30 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified20.7 (10.2-32.6) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified<79.14 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified14.0 +/- 7.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified22.99 (19.74-38.23) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified17-25 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified7.3 (0.1-29.3) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified24.1 (3.4-54.2) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified5.3 (2.9-10.4) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified3.1 (1.9-11.3) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified<7.6 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified18.6 (4.5-24.9) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified5-44 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified87.00 (13.00-161.00) uMAdult (>18 years old)BothGlutathione synthetase deficiency
    • MetaGene: Metabol...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
BloodDetected and Quantified3.5 (3.00-4.00) uMChildren (1-13 years old)BothGlutathione synthetase deficiency
    • MetaGene: Metabol...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified2326.0 uMAdult (>18 years old)BothPyroglutamic aciduria details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Calculus details
SalivaDetected and Quantified0.481 +/- 0.853 uMAdult (>18 years old)BothDental caries
    • Sugimoto et al. (...
 details
UrineDetected and Quantified28.8 (3.4-54.2) umol/mmol creatinineAdult (>18 years old)Both5-oxoprolinase deficiency
    • MetaGene: Metabol...
 details
UrineDetected and Quantified3500.0 (1000.0-6000.0) umol/mmol creatinineChildren (1-13 years old)Both5-Oxoprolinase Deficiency
    • MetaGene: Metabol...
 details
UrineDetected and Quantified7931-13208 umol/mmol creatinineChildren (1-13 years old)MalePyroglutamic aciduria details
UrineDetected and Quantified9-7282 umol/mmol creatinineInfant (0-1 year old)FemalePyroglutamic aciduria details
UrineDetected and Quantified34.75 +/- 17.53 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
UrineDetected and Quantified1.9 umol/mmol creatinineAdult (>18 years old)BothPyroglutamic aciduria details
UrineDetected and Quantified5570 umol/mmol creatinineChildren (1-13 years old)Not Specified5-Oxoprolinase Deficiency details
UrineDetected and Quantified1980 - 6040 umol/mmol creatinineInfant (0-1 year old)Not Specified
5-Oxoprolinase Deficiency		 details
UrineDetected and Quantified137.6 - 4092.79 umol/mmol creatinineChildren (1 - 13 years old)BothGlutathione synthetase deficiency details
UrineDetected and Quantified47.522 +/- 35.017 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified80.794 +/- 83.738 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Glutathione synthetase deficiency
  1. Li X, Ding Y, Liu Y, Ma Y, Song J, Wang Q, Yang Y: Five Chinese patients with 5-oxoprolinuria due to glutathione synthetase and 5-oxoprolinase deficiencies. Brain Dev. 2015 Nov;37(10):952-9. doi: 10.1016/j.braindev.2015.03.005. Epub 2015 Apr 4. [PubMed:25851806 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ulcerative colitis
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Supragingival Calculus
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
5-oxoprolinase deficiency
  1. Calpena E, Deshpande AA, Yap S, Kumar A, Manning NJ, Bachhawat AK, Espinos C: New insights into the genetics of 5-oxoprolinase deficiency and further evidence that it is a benign biochemical condition. Eur J Pediatr. 2015 Mar;174(3):407-11. doi: 10.1007/s00431-014-2397-0. Epub 2014 Aug 17. [PubMed:25129617 ]
  2. Mayatepek E: 5-Oxoprolinuria in patients with and without defects in the gamma-glutamyl cycle. Eur J Pediatr. 1999 Mar;158(3):221-5. [PubMed:10094443 ]
  3. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 266130 (Glutathione synthetase deficiency)
  • 181500 (Schizophrenia)
  • 114500 (Colorectal cancer)
  • 260005 (5-oxoprolinase deficiency)
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB03088
Phenol Explorer Compound IDNot Available
FooDB IDFDB014506
KNApSAcK IDC00007403
Chemspider IDNot Available
KEGG Compound IDC01879
BioCyc ID5-OXOPROLINE
BiGG IDNot Available
Wikipedia LinkPyroglutamic_acid
METLIN IDNot Available
PubChem Compound7405
PDB IDNot Available
ChEBI ID18183
Food Biomarker OntologyNot Available
VMH ID5OXPRO
MarkerDB IDMDB00000129
Good Scents IDNot Available
References
Synthesis ReferencePumpor, 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
  1. 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 ]
  2. 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 ]
  3. 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. [PubMed:8412012 ]
  4. 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 ]
  5. 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 ]
  6. 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. [PubMed:7937585 ]
  7. 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. [PubMed:11231318 ]
  8. 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. [PubMed:6441390 ]
  9. Creer MH, Lau BW, Jones JD, Chan KM: Pyroglutamic acidemia in an adult patient. Clin Chem. 1989 Apr;35(4):684-6. [PubMed:2702756 ]
  10. 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. [PubMed:2093471 ]
  11. 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. [PubMed:2971422 ]
  12. 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 ]
  13. 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. [PubMed:1572287 ]
  14. 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. [PubMed:8295398 ]
  15. 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. [PubMed:1225334 ]
  16. 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. [PubMed:15238252 ]
  17. 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 ]
  18. 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 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Glutaminyl-peptide cyclotransferase
General function:
Involved in peptidase activity
Specific function:
Responsible for the biosynthesis of pyroglutamyl peptides. Has a bias against acidic and tryptophan residues adjacent to the N-terminal glutaminyl residue and a lack of importance of chain length after the second residue. Also catalyzes N-terminal pyroglutamate formation. In vitro, catalyzes pyroglutamate formation of N-terminally truncated form of APP amyloid-beta peptides [Glu-3]-beta-amyloid. May be involved in the N-terminal pyroglutamate formation of several amyloid-related plaque-forming peptides.
Gene Name:
QPCT
Uniprot ID:
Q16769
Molecular weight:
40876.14
Enzyme Details
2. 5-oxoprolinase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the cleavage of 5-oxo-L-proline to form L-glutamate coupled to the hydrolysis of ATP to ADP and inorganic phosphate.
Gene Name:
OPLAH
Uniprot ID:
O14841
Molecular weight:
137456.195
Reactions
Adenosine triphosphate + Pyroglutamic acid + Water → ADP + Phosphate + L-Glutamic aciddetails
Enzyme Details
3. Angiogenin
General function:
Involved in nucleic acid binding
Specific function:
May function as a tRNA-specific ribonuclease that binds to actin on the surface of endothelial cells; once bound, angiogenin is endocytosed and translocated to the nucleus, thereby promoting the endothelial invasiveness necessary for blood vessel formation. Angiogenin induces vascularization of normal and malignant tissues. Abolishes protein synthesis by specifically hydrolyzing cellular tRNAs
Gene Name:
ANG
Uniprot ID:
P03950
Molecular weight:
16549.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
4. Ig lambda chain V-II region MGC
General function:
Involved in antigen binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P01709
Molecular weight:
11557.5
Enzyme Details
5. Alpha-amylase 1
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY1A
Uniprot ID:
P04745
Molecular weight:
Not Available
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
6. Pancreatic alpha-amylase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY2A
Uniprot ID:
P04746
Molecular weight:
Not Available
Enzyme Details
7. Vascular endothelial growth factor A
General function:
Involved in growth factor activity
Specific function:
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of blood vessels. Binds to the FLT1/VEGFR1 and KDR/VEGFR2 receptors, heparan sulfate and heparin. NRP1/Neuropilin-1 binds isoforms VEGF-165 and VEGF-145. Isoform VEGF165B binds to KDR but does not activate downstream signaling pathways, does not activate angiogenesis and inhibits tumor growth
Gene Name:
VEGFA
Uniprot ID:
P15692
Molecular weight:
27042.2
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
8. Alpha-amylase 2B
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY2B
Uniprot ID:
P19961
Molecular weight:
Not Available
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
9. Orexin
General function:
Involved in neuropeptide signaling pathway
Specific function:
Neuropeptides that play a significant role in the regulation of food intake and sleep-wakefulness, possibly by coordinating the complex behavioral and physiologic responses of these complementary homeostatic functions. A broader role in the homeostatic regulation of energy metabolism, autonomic function, hormonal balance and the regulation of body fluids, is also suggested. Orexin-A binds to both OX1R and OX2R with a high affinity, whereas orexin-B binds only to OX2R with a similar high affinity
Gene Name:
HCRT
Uniprot ID:
O43612
Molecular weight:
13362.5
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
10. Gamma-glutamylcyclotransferase
General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the formation of 5-oxoproline from gamma-glutamyl dipeptides and may play a significant role in glutathione homeostasis. Induces release of cytochrome c from mitochondria with resultant induction of apoptosis.
Gene Name:
GGCT
Uniprot ID:
O75223
Molecular weight:
19091.635
Reactions
(Gamma-L-glutamyl)-L-amino acid → Pyroglutamic acid + L-amino aciddetails
gamma-Glutamylcysteine → Pyroglutamic acid + L-Cysteinedetails
(5-L-Glutamyl)-L-amino acid → Pyroglutamic acid + L-Amino aciddetails

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters