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Showing NP-Card for Pyrrolidonecarboxylic acid (NP0334078)

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Record Information
Version2.0
Created at2024-09-09 22:05:14 UTC
Updated at2024-09-09 22:05:14 UTC
NP-MRD IDNP0334078
Secondary Accession NumbersNone
Natural Product Identification
Common NamePyrrolidonecarboxylic acid
Description2-Pyrrolidone-5-carboxylic acid (PCA) is a cyclic derivative of glutamic acid, physiologically present in mammalian tissues. It has been shown that PCA 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, PCA significantly shortens the plasma half-life of ethanol during acute intoxication. [HMDB]
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334078 (Pyrrolidonecarboxylic acid)


  Mrv1652305221920512D          

  9  9  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
M  END
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3D MOL for NP0334078 (Pyrrolidonecarboxylic acid)

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3D SDF for NP0334078 (Pyrrolidonecarboxylic acid)

  Mrv1652305221920512D          

  9  9  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334078

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)N1CCCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9)

> <INCHI_KEY>
DQAKJEWZWDQURW-UHFFFAOYSA-N

> <FORMULA>
C5H7NO3

> <MOLECULAR_WEIGHT>
129.114

> <EXACT_MASS>
129.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.695303950450285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopyrrolidine-1-carboxylic acid

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-0.11760391266666681

> <ALOGPS_LOGS>
0.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.437583879382684

> <JCHEM_PKA_STRONGEST_BASIC>
-8.702932492302965

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
28.678300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-pyroglutamate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334078 (Pyrrolidonecarboxylic acid)
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PDB for NP0334078 (Pyrrolidonecarboxylic acid)
HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.795   0.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    6    7                                                  
CONECT    5    6    8    9                                                  
CONECT    6    3    4    5                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0334078 (Pyrrolidonecarboxylic acid)
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SMILES for NP0334078 (Pyrrolidonecarboxylic acid)
OC(=O)N1CCCC1=O
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INCHI for NP0334078 (Pyrrolidonecarboxylic acid)
InChI=1S/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9)
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Synonyms
ValueSource
PyrrolidonecarboxylateGenerator
Chemical FormulaC5H7NO3
Average Mass129.1140 Da
Monoisotopic Mass129.04259 Da
IUPAC Name2-oxopyrrolidine-1-carboxylic acid
Traditional Name(+)-pyroglutamate
CAS Registry NumberNot Available
SMILES
OC(=O)N1CCCC1=O
InChI Identifier
InChI=1S/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9)
InChI KeyDQAKJEWZWDQURW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxoprolines. Oxoprolines are compounds containing an oxoproline moiety, which consists of a pyrrolidine ring bearing a carboxylic acid group at the ring position 2, and a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolidines  
Sub ClassPyrrolidones  
Direct ParentOxoprolines  
Alternative Parents
Substituents
  • Oxoproline
    • 

  • Pyrrolidine carboxylic acid
    • 

  • Pyrrolidine carboxylic acid or derivatives
    • 

  • 2-pyrrolidone
    • 

  • Dicarboximide
    • 

  • Carbonic acid derivative
    • 

  • Lactam
    • 

  • Carbamic acid derivative
    • 

  • Carbamic acid
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.12ALOGPS
logP-0.12ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.68 m³·mol⁻¹ChemAxon
Polarizability11.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022254  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyroglutamic acid  
METLIN IDNot Available
PubChem Compound9855476  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available