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Showing NP-Card for 2-Pyrrolidinone (NP0000769)

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Record Information
Version1.0
Created at2006-05-22 14:17:33 UTC
Updated at2021-10-07 20:42:22 UTC
NP-MRD IDNP0000769
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Pyrrolidinone
Description2-Pyrrolidinone is a lactam cyclization product of gamma-aminobutyric acid (GABA) (PMID 10332870 ). Vigabatrin (VGB, an antiepileptic drug) increases human brain gamma-aminobutyric acid (GABA) and the related metabolites, including 2-pyrrolidinone. Patients taking VGB are expected to have an increase of these metabolites (PMID 10403220 , 10840398 ). 2-Pyrrolidone is an organic compound consisting of a five-membered lactam. It is a colorless liquid which is used in industrial settings as a high-boiling non-corrosive polar solvent for a wide variety of applications. It is miscible with a wide variety of other solvents including water, ethanol, diethyl ether, chloroform, benzene, ethyl acetate and carbon disulfide.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000769 (2-Pyrrolidinone)


  Mrv1652305261923552D          

  6  6  0  0  0  0            999 V2000
   18.7986   -4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3466   -4.6966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6791   -4.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9340   -3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7591   -3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0140   -4.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000769 (2-Pyrrolidinone)

HMDB0002039
     RDKit          3D
2-Pyrrolidinone
 13 13  0  0  0  0  0  0  0  0999 V2000
   -0.4986    2.4344    0.7192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972    1.2474    0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004    0.0686    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654   -0.7911   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.6655   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0810    0.7760    0.0456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    0.3341    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0280   -0.4571    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -1.8102   -0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.2460   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -1.2614    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6567   -0.9463   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571    1.3171   -0.0480 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  2  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  6 13  1  0
M  END
Download

3D SDF for NP0000769 (2-Pyrrolidinone)


  Mrv1652305261923552D          

  6  6  0  0  0  0            999 V2000
   18.7986   -4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3466   -4.6966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6791   -4.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9340   -3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7591   -3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0140   -4.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)

> <INCHI_KEY>
HNJBEVLQSNELDL-UHFFFAOYSA-N

> <FORMULA>
C4H7NO

> <MOLECULAR_WEIGHT>
85.1045

> <EXACT_MASS>
85.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.701938043572053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyrrolidin-2-one

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-0.5796092983333335

> <ALOGPS_LOGS>
0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.745904083510304

> <JCHEM_PKA_STRONGEST_BASIC>
-1.826277890342777

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
22.2579

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrrolidone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000769 (2-Pyrrolidinone)

HMDB0002039
     RDKit          3D
2-Pyrrolidinone
 13 13  0  0  0  0  0  0  0  0999 V2000
   -0.4986    2.4344    0.7192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972    1.2474    0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004    0.0686    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654   -0.7911   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.6655   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0810    0.7760    0.0456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    0.3341    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0280   -0.4571    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -1.8102   -0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.2460   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -1.2614    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6567   -0.9463   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571    1.3171   -0.0480 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  2  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  6 13  1  0
M  END
Download

PDB for NP0000769 (2-Pyrrolidinone)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      35.091  -8.338   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      32.380  -8.767   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      31.134  -7.862   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.610  -6.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.150  -6.397   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.626  -7.862   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    6                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    2    5                                                  
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for NP0000769 (2-Pyrrolidinone)

COMPND    HMDB0002039
HETATM    1  O1  UNL     1      -0.499   2.434   0.719  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.197   1.247   0.449  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.100   0.069   0.487  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.465  -0.791  -0.603  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.995  -0.666  -0.239  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.081   0.776   0.046  1.00  0.00           N  
HETATM    7  H1  UNL     1      -2.145   0.334   0.249  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.028  -0.457   1.483  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.834  -1.810  -0.601  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.622  -0.246  -1.558  1.00  0.00           H  
HETATM   11  H5  UNL     1       1.200  -1.261   0.682  1.00  0.00           H  
HETATM   12  H6  UNL     1       1.657  -0.946  -1.065  1.00  0.00           H  
HETATM   13  H7  UNL     1       1.957   1.317  -0.048  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4    7    8
CONECT    4    5    9   10
CONECT    5    6   11   12
CONECT    6   13
END
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SMILES for NP0000769 (2-Pyrrolidinone)

O=C1CCCN1
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INCHI for NP0000769 (2-Pyrrolidinone)

InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
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View in JSmol
Synonyms
ValueSource
1-Azacyclopentan-2-oneChEBI
2-KetopyrrolidineChEBI
2-OxopyrrolidineChEBI
2-PyrrolidoneChEBI
4-Aminobutyric acid lactamChEBI
alpha-PyrrolidinoneChEBI
alpha-PyrrolidoneChEBI
ButyrolactamChEBI
gamma-Aminobutyric acid lactamChEBI
gamma-Aminobutyric lactamChEBI
gamma-ButyrolactamChEBI
PyrrolidinoneChEBI
PyrrolidoneChEBI
4-Aminobutyrate lactamGenerator
a-PyrrolidinoneGenerator
Α-pyrrolidinoneGenerator
a-PyrrolidoneGenerator
Α-pyrrolidoneGenerator
g-Aminobutyrate lactamGenerator
g-Aminobutyric acid lactamGenerator
gamma-Aminobutyrate lactamGenerator
Γ-aminobutyrate lactamGenerator
Γ-aminobutyric acid lactamGenerator
g-Aminobutyric lactamGenerator
Γ-aminobutyric lactamGenerator
g-ButyrolactamGenerator
Γ-butyrolactamGenerator
2-Pyrrolidone, hydrotribromideHMDB
2-Pyrrolidone, rubidium saltHMDB
2-Pyrrolidone, (18)O-labeledHMDB
2-Pyrrolidone, 5-(14)C-labeledHMDB
2-Pyrrolidone, potassium saltHMDB
2-Pyrrolidone, sodium saltHMDB
2-Pyrrolidone, aluminum saltHMDB
2-Pyrrolidone, cerium saltHMDB
2-Pyrrolidone, hydrobromideHMDB
2-Pyrrolidone, hydrochlorideHMDB
2-Pyrrolidone, lithium saltHMDB
1-Methyl-2-pyrrolidinoneHMDB
2-Pyrol4-aminobutyric acid lactamHMDB
2-Pyrrolidone for synthesisHMDB
2-Pyrrolidone-butyrolactamHMDB
Aminobutyric acid lactamHMDB
Aminobutyric lactamHMDB
AminobutyrolactamHMDB
N-Methyl-2-pyrrolidinoneHMDB
Pyrrolidin-2-oneHMDB
PyrrolidonHMDB
Pyrrolidone-2HMDB
TetrahydropyrroloneHMDB
2-PyrrolidinoneChEBI
Chemical FormulaC4H7NO
Average Mass85.1045 Da
Monoisotopic Mass85.05276 Da
IUPAC Namepyrrolidin-2-one
Traditional Namepyrrolidone
CAS Registry Number616-45-5
SMILES
O=C1CCCN1
InChI Identifier
InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
InChI KeyHNJBEVLQSNELDL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Averrhoa carambolaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capparis spinosaLOTUS Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Microtropis japonicaKNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vitis viniferaLOTUS Database
Species Where Detected
Species NameSourceReference
Phoma medicaginisKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentPyrrolidine-2-ones
Alternative Parents
Substituents
  • 2-pyrrolidone
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point23 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.85Sasaki, H., Mori, Y., Nakamura, J., & Shibasaki, J. (1991). Synthesis and anticonvulsant activity of 1-acyl-2-pyrrolidinone derivatives. Journal of medicinal chemistry, 34(2), 628-633.
Predicted Properties
PropertyValueSource
Water Solubility537 g/LALOGPS
logP-0.9ALOGPS
logP-0.58ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.26 m³·mol⁻¹ChemAxon
Polarizability8.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002039
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000741
KNApSAcK IDC00038233
Chemspider ID11530
KEGG Compound IDC11118
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Pyrrolidone
METLIN ID6452
PubChem Compound12025
PDB IDNot Available
ChEBI ID36592
Good Scents IDrw1180741
References
General References
  1. Petroff OA, Hyder F, Mattson RH, Rothman DL: Topiramate increases brain GABA, homocarnosine, and pyrrolidinone in patients with epilepsy. Neurology. 1999 Feb;52(3):473-8. [PubMed:10025774 ]
  2. Sun X, Qiao H, Jiang H, Zhi X, Liu F, Wang J, Liu M, Dong D, Kanwar JR, Xu R, Krissansen GW: Intramuscular delivery of antiangiogenic genes suppresses secondary metastases after removal of primary tumors. Cancer Gene Ther. 2005 Jan;12(1):35-45. [PubMed:15486558 ]
  3. Hyder F, Petroff OA, Mattson RH, Rothman DL: Localized 1H NMR measurements of 2-pyrrolidinone in human brain in vivo. Magn Reson Med. 1999 May;41(5):889-96. [PubMed:10332870 ]
  4. Rambabu K, Pattabiraman TN: Studies on gamma-glutamyl transpeptidase of human urine. Clin Chim Acta. 1976 Dec 1;73(2):251-5. [PubMed:11907 ]
  5. Matsudo T, Ogawa K, Kokufuta E: Complex formation of protein with different water-soluble synthetic polymers. Biomacromolecules. 2003 Nov-Dec;4(6):1794-9. [PubMed:14606910 ]
  6. Fedi AM, Leoncini P, Farella V, Lotti T: [Study of filaggrin in psoriasis]. G Ital Dermatol Venereol. 1989 Apr;124(4):141-5. [PubMed:2680915 ]
  7. Gobbels M, Spitznas M: Effects of artificial tears on corneal epithelial permeability in dry eyes. Graefes Arch Clin Exp Ophthalmol. 1991;229(4):345-9. [PubMed:1916322 ]
  8. Gobbels M, Spitznas M: Corneal epithelial permeability of dry eyes before and after treatment with artificial tears. Ophthalmology. 1992 Jun;99(6):873-8. [PubMed:1630776 ]
  9. Onorato JM, Henion JD, Lefebvre PM, Kiplinger JP: Selected reaction monitoring LC-MS determination of idoxifene and its pyrrolidinone metabolite in human plasma using robotic high-throughput, sequential sample injection. Anal Chem. 2001 Jan 1;73(1):119-25. [PubMed:11195494 ]
  10. Zimmermann W, Donhardt A, Braun W: [2-Br-2-ethyl-4-hydroxybutyramide and 2-Br-2-ethyl-4-butyrolactam as carbromal metabolites (author's transl)]. Arch Toxicol. 1978 Apr 27;40(2):119-24. [PubMed:26319 ]
  11. Voigt R, Korner I, Roth P: [Interactions between macromolecular adjuvants and drugs. Part 16: Effects of human serum albumin and Mg2+ on oxytetracycline-polyvinylpyrrolidone interactions (author's transl)]. Pharmazie. 1979 Jan;34(1):45-8. [PubMed:432255 ]
  12. Petroff OA, Hyder F, Collins T, Mattson RH, Rothman DL: Acute effects of vigabatrin on brain GABA and homocarnosine in patients with complex partial seizures. Epilepsia. 1999 Jul;40(7):958-64. [PubMed:10403220 ]
  13. Petroff OA, Hyder F, Rothman DL, Mattson RH: Effects of gabapentin on brain GABA, homocarnosine, and pyrrolidinone in epilepsy patients. Epilepsia. 2000 Jun;41(6):675-80. [PubMed:10840398 ]