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Showing NP-Card for n-nitrosomorpholine (NP0236762)

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Record Information
Version2.0
Created at2022-09-06 19:44:30 UTC
Updated at2022-09-06 19:44:30 UTC
NP-MRD IDNP0236762
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-nitrosomorpholine
DescriptionN-nitrosomorpholine belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. n-nitrosomorpholine is found in Nicotiana tabacum. n-nitrosomorpholine was first documented in 1977 (PMID: 20781). N-nitrosomorpholine is a strong basic compound (based on its pKa) (PMID: 15328583) (PMID: 21089935) (PMID: 21396674) (PMID: 21860513).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0236762 (n-nitrosomorpholine)


  Mrv1533004191516292D          

  8  8  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
Download

3D MOL for NP0236762 (n-nitrosomorpholine)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.8443    1.4209    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    1.5117   -0.5577 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    0.6873   -0.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8633   -0.7348   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767   -1.5002    0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084   -0.6124    1.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399    0.1698    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5723    1.3399   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -0.9609   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -1.0450   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863   -2.0985   -0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292   -2.1920    1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302    0.5175    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642   -0.3690   -0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.8889    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093    1.9769   -0.8644 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  1  0
  7  8  1  0
  8  3  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  7 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
M  END
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3D SDF for NP0236762 (n-nitrosomorpholine)


  Mrv1533004191516292D          

  8  8  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=NN1CCOCC1

> <INCHI_IDENTIFIER>
InChI=1S/C4H8N2O2/c7-5-6-1-3-8-4-2-6/h1-4H2

> <INCHI_KEY>
ZKXDGKXYMTYWTB-UHFFFAOYSA-N

> <FORMULA>
C4H8N2O2

> <MOLECULAR_WEIGHT>
116.12

> <EXACT_MASS>
116.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.919425995237926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-nitrosomorpholine

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-0.17988662933333335

> <ALOGPS_LOGS>
-0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.1448729139579634

> <JCHEM_POLAR_SURFACE_AREA>
41.900000000000006

> <JCHEM_REFRACTIVITY>
29.124999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-nitrosomorpholine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0236762 (n-nitrosomorpholine)

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PDB for NP0236762 (n-nitrosomorpholine)
HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0236762 (n-nitrosomorpholine)
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SMILES for NP0236762 (n-nitrosomorpholine)
O=NN1CCOCC1
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INCHI for NP0236762 (n-nitrosomorpholine)
InChI=1S/C4H8N2O2/c7-5-6-1-3-8-4-2-6/h1-4H2
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View in JSmol
Synonyms
ValueSource
N-NitrosomorpholinChEBI
NitrosomorpholineChEBI
alpha-Acetoxy-N-nitrosomorpholineMeSH
Chemical FormulaC4H8N2O2
Average Mass116.1200 Da
Monoisotopic Mass116.05858 Da
IUPAC Name4-nitrosomorpholine
Traditional NameN-nitrosomorpholine
CAS Registry NumberNot Available
SMILES
O=NN1CCOCC1
InChI Identifier
InChI=1S/C4H8N2O2/c7-5-6-1-3-8-4-2-6/h1-4H2
InChI KeyZKXDGKXYMTYWTB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Nicotiana tabacumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxazinanes  
Sub ClassMorpholines  
Direct ParentMorpholines  
Alternative Parents
Substituents
  • Morpholine
    • 

  • Organic n-nitroso compound
    • 

  • Organic nitroso compound
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • 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-0.61ALOGPS
logP-0.18ChemAxon
logS-0.1ALOGPS
pKa (Strongest Basic)3.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area41.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.12 m³·mol⁻¹ChemAxon
Polarizability10.92 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19283  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6046  
PDB IDNot Available
ChEBI ID76326  
Good Scents IDNot Available
References
General References
  1. Authors unspecified: N-Nitrosomorpholine. Rep Carcinog. 2002;10:185. [PubMed:15328583  ] 
  2. Reznik-Schuller H: Sequential morphologic alterations in the bronchial epithelium of Syrian golden hamsters during N-nitrosomorpholine-induced pulmonary tumorigenesis. Am J Pathol. 1977 Oct;89(1):59-66. [PubMed:20781  ] 
  3. Authors unspecified: N-Nitrosomorpholine. Rep Carcinog. 2004;11:III205-6. [PubMed:21089935  ] 
  4. Pitoi MM, Patterson BM, Furness AJ, Bastow TP, McKinley AJ: Fate of N-nitrosomorpholine in an anaerobic aquifer used for managed aquifer recharge: a column study. Water Res. 2011 Apr;45(8):2550-60. doi: 10.1016/j.watres.2011.02.018. Epub 2011  Feb 19. [PubMed:21396674  ] 
  5. Authors unspecified: N-Nitrosamines (15 listings): N-nitrosomorpholine. Rep Carcinog. 2011;12:319-20. [PubMed:21860513  ] 
  6. LOTUS database [Link]