Showing metabocard for Pyroglutamic acid (MMDBc0000509)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:23 UTC
Update Date2024-10-10 00:24:57 UTC
Metabolite IDMMDBc0000509
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c88930a0>

       
  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 #<Metabolite:0x00005645c88930a0>

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 #<Metabolite:0x00005645c88930a0>

       
  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>
MMDBc0000509

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00005645c88930a0>

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 #<Metabolite:0x00005645c88930a0>

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 #<Metabolite:0x00005645c88930a0>

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 #<Metabolite:0x00005645c88930a0>

OC(=O)[C@@H]1CCC(=O)N1
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INCHI for #<Metabolite:0x00005645c88930a0>

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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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
Molecular FormulaC5H7NO3
Average Mass129.114
Monoisotopic Mass129.042593095
IUPAC Name(2S)-5-oxopyrrolidine-2-carboxylic acid
Traditional Namepyroglutamic acid
CAS Registry NumberNot 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 KeyODHCTXKNWHHXJC-VKHMYHEASA-N