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Showing NP-Card for N-Methyl-2-pyrrolidone (NP0076908)

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Record Information
Version2.0
Created at2022-04-28 22:05:44 UTC
Updated at2022-04-28 22:05:44 UTC
NP-MRD IDNP0076908
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methyl-2-pyrrolidone
DescriptionMethyl pyrrolidone, also known as NMP or pharmasolve, belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. It is a colorless to slightly yellow liquid miscible with water. Methyl pyrrolidone is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methyl-2-pyrrolidone, or Methyl pyrrolidone (NMP), is a chemical compound with 5-membered lactam structure. Methyl pyrrolidone is a potentially toxic compound. These metabolites are all colourless. It is used in petrochemical processing, and as a solvent for surface treatment of textiles, resins and metal coated plastics or as a paint stripper. Methyl pyrrolidone has been identified as a reproductive toxicant, first by California in 2001 and then by the European Commission in 2003. The excreted amounts of Methyl pyrrolidone metabolites in the urine after inhalation or oral intake represented about 100% and 65% of the administered doses, respectively. Rapid, irregular respiration, shortnessof breath, decreased pain reflex, and slight bloody nasalsecretion. N-Methyl-2-pyrrolidone is found in Glycyrrhiza glabra, Melicope hayesii and Microtropis japonica. N-Methyl-2-pyrrolidone was first documented in 2013 (PMID: 23337464). In the pharmaceutical industry, Methyl pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes (PMID: 24446970).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0076908 (N-Methyl-2-pyrrolidone)


  Mrv0541 05041407262D          

  7  7  0  0  0  0            999 V2000
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -0.0997    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
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
M  END
Download

3D MOL for NP0076908 (N-Methyl-2-pyrrolidone)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.0415    0.7215   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    0.2790   -0.1533 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2671   -1.0726    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1791   -0.9414    0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249    0.2283   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056    1.0309   -0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640    2.2101   -0.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147    1.7873    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.1721    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4463    0.4743   -1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4925   -1.7972   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8569   -1.3459    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -0.6733    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119   -1.8798    0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240    0.8399    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323   -0.0334   -1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
M  END
Download

3D SDF for NP0076908 (N-Methyl-2-pyrrolidone)


  Mrv0541 05041407262D          

  7  7  0  0  0  0            999 V2000
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -0.0997    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
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0076908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3

> <INCHI_KEY>
SECXISVLQFMRJM-UHFFFAOYSA-N

> <FORMULA>
C5H9NO

> <MOLECULAR_WEIGHT>
99.1311

> <EXACT_MASS>
99.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
10.70290517539099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methylpyrrolidin-2-one

> <ALOGPS_LOGP>
-0.72

> <JCHEM_LOGP>
-0.35593323266666665

> <ALOGPS_LOGS>
0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9968110272926051

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
27.1546

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.53e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylpyrrolidone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0076908 (N-Methyl-2-pyrrolidone)

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PDB for NP0076908 (N-Methyl-2-pyrrolidone)
HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    1    4    5                                                  
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0076908 (N-Methyl-2-pyrrolidone)
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SMILES for NP0076908 (N-Methyl-2-pyrrolidone)
CN1CCCC1=O
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INCHI for NP0076908 (N-Methyl-2-pyrrolidone)
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
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View in JSmol
Synonyms
ValueSource
1-Methyl-2-pyrrolidinoneChEBI
1-Methylazacyclopentan-2-oneChEBI
N-Methyl-2-pyrrolidinoneChEBI
N-Methyl-alpha-pyrrolidinoneChEBI
N-Methyl-alpha-pyrrolidoneChEBI
N-Methyl-gamma-butyrolactamChEBI
NMPChEBI
N-MethylpyrrolidoneKegg
N-Methyl-a-pyrrolidinoneGenerator
N-Methyl-α-pyrrolidinoneGenerator
N-Methyl-a-pyrrolidoneGenerator
N-Methyl-α-pyrrolidoneGenerator
N-Methyl-g-butyrolactamGenerator
N-Methyl-γ-butyrolactamGenerator
1-Methyl-2-pyrrolidinone, 2,3,4,5-(14)C-labeledMeSH
N-MethylpyrrolidinoneMeSH
1-Methyl-2-pyrrolidinone, 1-methyl-(14)C-labeledMeSH
PharmasolveMeSH
N-Methyl-2-pyrrolidoneMeSH
Methyl pyrrolidoneMeSH
Chemical FormulaC5H9NO
Average Mass99.1311 Da
Monoisotopic Mass99.06841 Da
IUPAC Name1-methylpyrrolidin-2-one
Traditional Namemethylpyrrolidone
CAS Registry NumberNot Available
SMILES
CN1CCCC1=O
InChI Identifier
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
InChI KeySECXISVLQFMRJM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycyrrhiza glabraLOTUS Database
Melicope hayesiiLOTUS Database
Microtropis japonicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolidines  
Sub ClassN-alkylpyrrolidines  
Direct ParentN-alkylpyrrolidines  
Alternative Parents
Substituents
  • Pyrrolidone
    • 

  • 2-pyrrolidone
    • 

  • N-alkylpyrrolidine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • 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 Descriptors
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-0.72ALOGPS
logP-0.36ChemAxon
logS0.93ALOGPS
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.15 m³·mol⁻¹ChemAxon
Polarizability10.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB12521  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00039855  
Chemspider IDNot Available
KEGG Compound IDC11118  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyl-2-pyrrolidone  
METLIN IDNot Available
PubChem Compound13387  
PDB IDNot Available
ChEBI ID7307  
Good Scents IDNot Available
References
General References
  1. Meier S, Schindler BK, Koslitz S, Koch HM, Weiss T, Kafferlein HU, Bruning T: Biomonitoring of exposure to N-methyl-2-pyrrolidone in workers of the automobile industry. Ann Occup Hyg. 2013 Jul;57(6):766-73. doi: 10.1093/annhyg/mes111. Epub 2013 Jan 20. [PubMed:23337464  ] 
  2. Cilurzo F, Vistoli G, Selmin F, Gennari CG, Musazzi UM, Franze S, Lo Monte M, Minghetti P: An insight into the skin penetration enhancement mechanism of N-methylpyrrolidone. Mol Pharm. 2014 Mar 3;11(3):1014-21. doi: 10.1021/mp400675d. Epub 2014 Jan 30. [PubMed:24446970  ]