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Showing NP-Card for 9-Azabicyclo[3.3.1]nonan-3-one (NP0045427)

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Record Information
Version2.0
Created at2022-03-17 19:19:47 UTC
Updated at2022-03-17 19:19:47 UTC
NP-MRD IDNP0045427
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Azabicyclo[3.3.1]nonan-3-one
Description9-Azabicyclo[3.3.1]Nonan-3-one, also known as alpha-phosphinylbenzyl alcohol or granatonine, belongs to the class of organic compounds known as piperidinones. Piperidinones are compounds containing a piperidine ring which bears a ketone. 9-Azabicyclo[3.3.1]Nonan-3-one is a very strong basic compound (based on its pKa). Outside of the human body, 9-Azabicyclo[3.3.1]Nonan-3-one has been detected, but not quantified in, fruits and pomegranates. This could make 9-azabicyclo[3.3.1]Nonan-3-one a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)


  Mrv0541 05061304502D          

 10 11  0  0  0  0            999 V2000
    0.1160   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2412   -0.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140   -0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079   -1.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1484   -0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616   -0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022   -2.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -0.1198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -2.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
Download

3D MOL for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.8744    1.7599    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568    1.1893   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357   -0.2870   -0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413   -1.0095    0.5370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3741   -1.5603   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -0.9696   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    0.5902   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644    0.8362   -0.0468 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5394    1.9601   -0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810    0.1132    1.1687 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934   -0.5772   -1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7951   -0.6846    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513   -1.7270    1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361   -1.6484   -1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022   -2.6300    0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3755   -1.2962   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -1.3414    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.9537   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182    0.9071    0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    0.3342   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5006    2.6581   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811    2.5409    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478   -0.1115    1.8294 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  9  1  0
  8 10  1  0
  9  2  1  0
 10  4  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  1
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  6
  9 21  1  0
  9 22  1  0
 10 23  1  0
M  END
Download

3D SDF for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)


  Mrv0541 05061304502D          

 10 11  0  0  0  0            999 V2000
    0.1160   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2412   -0.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140   -0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079   -1.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1484   -0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616   -0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022   -2.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -0.1198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -2.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CC2CCCC(C1)N2

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO/c10-8-4-6-2-1-3-7(5-8)9-6/h6-7,9H,1-5H2

> <INCHI_KEY>
JIYPUEZSSJAXBO-UHFFFAOYSA-N

> <FORMULA>
C8H13NO

> <MOLECULAR_WEIGHT>
139.1949

> <EXACT_MASS>
139.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
15.1936007384924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-azabicyclo[3.3.1]nonan-3-one

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.7599851263333334

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.085684596852918

> <JCHEM_PKA_STRONGEST_BASIC>
8.192861458727556

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
38.651199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-azabicyclo[3.3.1]nonan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)

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PDB for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.216  -2.506   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.450  -1.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.146  -1.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.257  -2.783   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.001  -3.523   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.144  -1.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.915  -1.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.497  -3.853   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.157  -0.224   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.230  -4.693   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    2    4    9                                                  
CONECT    7    3    5    9                                                  
CONECT    8    4    5   10                                                  
CONECT    9    6    7                                                       
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)
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SMILES for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)
O=C1CC2CCCC(C1)N2
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INCHI for NP0045427 (9-Azabicyclo[3.3.1]nonan-3-one)
InChI=1S/C8H13NO/c10-8-4-6-2-1-3-7(5-8)9-6/h6-7,9H,1-5H2
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View in JSmol
Synonyms
ValueSource
9-Azabicyclo(3.3.1)nonan-3-oneHMDB
alpha-Phosphinylbenzyl alcoholHMDB
GranatonineHMDB
Norgranatan-3-oneHMDB
NorpseudopelletierineHMDB
Chemical FormulaC8H13NO
Average Mass139.1949 Da
Monoisotopic Mass139.09971 Da
IUPAC Name9-azabicyclo[3.3.1]nonan-3-one
Traditional Name9-azabicyclo[3.3.1]nonan-3-one
CAS Registry Number4390-39-0
SMILES
O=C1CC2CCCC(C1)N2
InChI Identifier
InChI=1S/C8H13NO/c10-8-4-6-2-1-3-7(5-8)9-6/h6-7,9H,1-5H2
InChI KeyJIYPUEZSSJAXBO-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
Punica granatumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as piperidinones. Piperidinones are compounds containing a piperidine ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPiperidines  
Sub ClassPiperidinones  
Direct ParentPiperidinones  
Alternative Parents
Substituents
  • Piperidinone
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Secondary aliphatic amine
    • 

  • Secondary amine
    • 

  • Azacycle
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP0.47ALOGPS
logP0.76ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)8.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.65 m³·mol⁻¹ChemAxon
Polarizability15.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029613  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000781  
KNApSAcK IDNot Available
Chemspider ID128569  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound145745  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available