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Showing NP-Card for Ethylenimine (NP0045141)

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Record Information
Version2.0
Created at2022-03-10 18:58:40 UTC
Updated at2022-03-10 22:20:40 UTC
NP-MRD IDNP0045141
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthylenimine
DescriptionEthylenimine, also known as aziridine or azacyclopropane, belongs to the class of organic compounds known as aziridines. These are organic compounds containing a saturated three-member heterocycle with one amino group and two methylene groups. Ethylenimine is a very strong basic compound (based on its pKa). Ethylenimine consists of a three-membered heterocycle (CH2)2NH. It is a colorless, toxic, volatile liquid that is of significant practical interest. Ethylen imine is produced industrially from aminoethanol via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to affect the dehydration. In the Wenker synthesis, the aminoethanol is converted to the sulfate ester, which undergoes base-induced sulfate elimination. Older methods entailed amination of 1,2-dichloroethane and cyclization of 2-chloroethylamine. Ethylenimine has been reported to be found in soybean and wild celery. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045141 (Ethylenimine)


  Mrv1652303202019012D          

  3  3  0  0  0  0            999 V2000
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
M  END
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3D MOL for NP0045141 (Ethylenimine)

     RDKit          3D

  8  8  0  0  0  0  0  0  0  0999 V2000
   -0.7641   -0.1905    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349   -0.4459   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518    0.7949   -0.5820 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1312    0.1760    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5049   -0.5281   -0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -1.1919   -0.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3267   -0.3068    0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866    1.6923   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  1  1  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  0
M  END
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3D SDF for NP0045141 (Ethylenimine)


  Mrv1652303202019012D          

  3  3  0  0  0  0            999 V2000
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CN1

> <INCHI_IDENTIFIER>
InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2

> <INCHI_KEY>
NOWKCMXCCJGMRR-UHFFFAOYSA-N

> <FORMULA>
C2H5N

> <MOLECULAR_WEIGHT>
43.0678

> <EXACT_MASS>
43.042199165

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
4.899903295417076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
aziridine

> <ALOGPS_LOGP>
-1.07

> <JCHEM_LOGP>
-0.364403415

> <ALOGPS_LOGS>
1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.035344037839952

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
12.7244

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.41e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aziridine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045141 (Ethylenimine)

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PDB for NP0045141 (Ethylenimine)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.325   0.325   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    3                                                       
CONECT    3    2    1                                                       
MASTER        0    0    0    0    0    0    0    0    3    0    6    0
END

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3D PDB for NP0045141 (Ethylenimine)
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SMILES for NP0045141 (Ethylenimine)
C1CN1
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INCHI for NP0045141 (Ethylenimine)
InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
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View in JSmol
Synonyms
ValueSource
AzacyclopropaneChEBI
DimethyleneimineChEBI
EIChEBI
EthyleneimineChEBI
EthylenimineChEBI
Aziridine, conjugate acidMeSH
Chemical FormulaC2H5N
Average Mass43.0678 Da
Monoisotopic Mass43.04220 Da
IUPAC Nameaziridine
Traditional Nameaziridine
CAS Registry Number81210-08-4
SMILES
C1CN1
InChI Identifier
InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
InChI KeyNOWKCMXCCJGMRR-UHFFFAOYSA-N
Experimental Spectra
Not Available
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
Cannabis sativaNULL
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aziridines. These are organic compounds containing a saturated three-member heterocycle with one amino group and two methylene groups.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAziridines  
Sub ClassNot Available
Direct ParentAziridines  
Alternative Parents
Substituents
  • Azacycle
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Aziridine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • 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-1.1ALOGPS
logP-0.36ChemAxon
logS1.17ALOGPS
pKa (Strongest Basic)8.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity12.72 m³·mol⁻¹ChemAxon
Polarizability4.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003941  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11687  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlucosidases  
METLIN IDNot Available
PubChem Compound9033  
PDB IDNot Available
ChEBI ID30969  
Good Scents IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499  ]