Np mrd loader

Showing NP-Card for Pseudooxynicotine (NP0086734)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-05-11 16:29:30 UTC
Updated at2022-05-11 16:29:30 UTC
NP-MRD IDNP0086734
Secondary Accession NumbersNone
Natural Product Identification
Common NamePseudooxynicotine
DescriptionPseudooxynicotine belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. Pseudooxynicotine is a very strong basic compound (based on its pKa). Pseudooxynicotine was first documented in 2007 (PMID: 17464070). An aminoacylpyridine that is pyridine substituted at position 3 by a 4-(methylamino)butanoyl group (PMID: 22267672) (PMID: 18203859) (PMID: 19060159) (PMID: 21637938).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086734 (Pseudooxynicotine)


  Mrv0541 02231219002D          

 13 13  0  0  0  0            999 V2000
    5.0073  -10.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198  -11.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073  -12.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823  -12.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699  -11.6077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823  -10.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198  -10.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073   -9.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198   -8.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073   -8.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198   -7.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073   -6.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2448  -10.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  2  0  0  0  0
M  END
Download

3D MOL for NP0086734 (Pseudooxynicotine)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.5361    1.3723    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    0.0237    0.6102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6157   -0.9349   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.0470   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -1.4792    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -1.5565    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -2.7039   -0.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -0.3982    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928    0.8510    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779    1.8981    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690    1.7084    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0980    0.4767   -0.3555 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389   -0.5549   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5155    1.8907    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9332    1.8264    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766    1.4594   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -0.1264    1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1123   -0.5340   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1054   -1.9056   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8831   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.1001   -1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.4248    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4293   -0.7307    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4456    1.0097    0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0290    2.8768    0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062    2.5217   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212   -1.5356   -0.6277 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  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0086734 (Pseudooxynicotine)


  Mrv0541 02231219002D          

 13 13  0  0  0  0            999 V2000
    5.0073  -10.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198  -11.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073  -12.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823  -12.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699  -11.6077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823  -10.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198  -10.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073   -9.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198   -8.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073   -8.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4198   -7.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073   -6.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2448  -10.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCCCC(=O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O/c1-11-6-3-5-10(13)9-4-2-7-12-8-9/h2,4,7-8,11H,3,5-6H2,1H3

> <INCHI_KEY>
SGDIDUFQYHRMPR-UHFFFAOYSA-N

> <FORMULA>
C10H14N2O

> <MOLECULAR_WEIGHT>
178.231

> <EXACT_MASS>
178.11061308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.19533049172019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(methylamino)-1-(pyridin-3-yl)butan-1-one

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.34734540000000025

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.844110312826558

> <JCHEM_PKA_STRONGEST_BASIC>
10.276879573131845

> <JCHEM_POLAR_SURFACE_AREA>
41.99

> <JCHEM_REFRACTIVITY>
51.8926

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pseudooxynicotine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086734 (Pseudooxynicotine)

Download
PDB for NP0086734 (Pseudooxynicotine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       9.347 -20.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.117 -21.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.347 -23.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.807 -23.001   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       7.037 -21.668   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.807 -20.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.117 -19.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.347 -17.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.117 -16.333   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.347 -14.999   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.117 -13.666   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.347 -12.332   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.657 -19.000   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0086734 (Pseudooxynicotine)
Download
SMILES for NP0086734 (Pseudooxynicotine)
CNCCCC(=O)C1=CC=CN=C1
Download
INCHI for NP0086734 (Pseudooxynicotine)
InChI=1S/C10H14N2O/c1-11-6-3-5-10(13)9-4-2-7-12-8-9/h2,4,7-8,11H,3,5-6H2,1H3
Download
View in JSmol
Synonyms
ValueSource
4-(Methylamino)-1-(3-pyridinyl)-1-butanoneChEBI
4-(Methylamino)-1-(3-pyridyl)-1-butanoneChEBI
4-(Methylamino)-1-(pyridin-3-yl)butan-1-oneKegg
Chemical FormulaC10H14N2O
Average Mass178.2310 Da
Monoisotopic Mass178.11061 Da
IUPAC Name4-(methylamino)-1-(pyridin-3-yl)butan-1-one
Traditional Namepseudooxynicotine
CAS Registry NumberNot Available
SMILES
CNCCCC(=O)C1=CC=CN=C1
InChI Identifier
InChI=1S/C10H14N2O/c1-11-6-3-5-10(13)9-4-2-7-12-8-9/h2,4,7-8,11H,3,5-6H2,1H3
InChI KeySGDIDUFQYHRMPR-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAryl alkyl ketones  
Alternative Parents
Substituents
  • Aryl alkyl ketone
    • 

  • Pyridine
    • 

  • Gamma-aminoketone
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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
logP0.36ALOGPS
logP0.35ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)15.84ChemAxon
pKa (Strongest Basic)10.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.89 m³·mol⁻¹ChemAxon
Polarizability20.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001240  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022506  
KNApSAcK IDNot Available
Chemspider ID421  
KEGG Compound IDC20361  
BioCyc IDCPD-14092  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6100  
PubChem Compound434  
PDB IDNot Available
ChEBI ID37753  
Good Scents IDNot Available
References
General References
  1. Wang SN, Liu Z, Tang HZ, Meng J, Xu P: Characterization of environmentally friendly nicotine degradation by Pseudomonas putida biotype A strain S16. Microbiology (Reading). 2007 May;153(Pt 5):1556-1565. doi: 10.1099/mic.0.2006/005223-0. [PubMed:17464070  ] 
  2. Qiu J, Ma Y, Wen Y, Chen L, Wu L, Liu W: Functional identification of two novel genes from Pseudomonas sp. strain HZN6 involved in the catabolism of nicotine. Appl Environ Microbiol. 2012 Apr;78(7):2154-60. doi: 10.1128/AEM.07025-11. Epub 2012 Jan 20. [PubMed:22267672  ] 
  3. Tang H, Wang S, Ma L, Meng X, Deng Z, Zhang D, Ma C, Xu P: A novel gene, encoding 6-hydroxy-3-succinoylpyridine hydroxylase, involved in nicotine degradation by Pseudomonas putida strain S16. Appl Environ Microbiol. 2008 Mar;74(5):1567-74. doi: 10.1128/AEM.02529-07. Epub 2008 Jan 18. [PubMed:18203859  ] 
  4. Tang H, Wang L, Meng X, Ma L, Wang S, He X, Wu G, Xu P: Novel nicotine oxidoreductase-encoding gene involved in nicotine degradation by Pseudomonas putida strain S16. Appl Environ Microbiol. 2009 Feb;75(3):772-8. doi: 10.1128/AEM.02300-08. Epub 2008 Dec 5. [PubMed:19060159  ] 
  5. Qiu J, Ma Y, Chen L, Wu L, Wen Y, Liu W: A sirA-like gene, sirA2, is essential for 3-succinoyl-pyridine metabolism in the newly isolated nicotine-degrading Pseudomonas sp. HZN6 strain. Appl Microbiol Biotechnol. 2011 Dec;92(5):1023-32. doi: 10.1007/s00253-011-3353-9. Epub 2011 Jun 3. [PubMed:21637938  ]