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Showing NP-Card for 11-Oxocytisine (NP0055134)

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Record Information
Version2.0
Created at2022-04-28 01:15:56 UTC
Updated at2022-04-28 01:15:56 UTC
NP-MRD IDNP0055134
Secondary Accession NumbersNone
Natural Product Identification
Common Name11-Oxocytisine
Description(1S,9S)-10-hydroxy-7,11-diazatricyclo[7.3.1.0²,⁷]Trideca-2,4,10-trien-6-one belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one. 11-Oxocytisine is found in Sophora secundiflora . Based on a literature review very few articles have been published on (1S,9S)-10-hydroxy-7,11-diazatricyclo[7.3.1.0²,⁷]Trideca-2,4,10-trien-6-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0055134 (11-Oxocytisine)


  Mrv1652304282203152D          

 15 17  0  0  1  0            999 V2000
    4.1130    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -1.0845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7469    0.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6877    0.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    1.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0641    1.4615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9797    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840   -0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2069   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227   -0.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.7787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    1.4024    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
Download

3D MOL for NP0055134 (11-Oxocytisine)

     RDKit          3D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.4264   -2.2194    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0681   -1.1708    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    0.1091    0.9891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828    1.2810    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660    1.1038   -0.4774 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3518    0.1416   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005   -1.2421   -0.8010 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1032   -1.6831   -0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0020   -0.6481   -0.1568 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728    0.6359   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5746    1.6108    0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313    1.2175    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2054   -0.1117    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -1.0126    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726   -2.2458    0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    0.2555    1.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978    1.5053    1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678    2.1623    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5476    2.0761   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    0.1662   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258    0.4330   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795   -1.9262   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905   -2.0360   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524   -2.5617    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2899    2.6480    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5822    1.9143    1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037   -0.4029    0.9553 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
  9 14  1  0
 14 15  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
  7  2  1  0
 10  9  1  0
 10  5  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  6
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
 13 27  1  0
 12 26  1  0
 11 25  1  0
M  END
Download

3D SDF for NP0055134 (11-Oxocytisine)


  Mrv1652304282203152D          

 15 17  0  0  1  0            999 V2000
    4.1130    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -1.0845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7469    0.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6877    0.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    1.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0641    1.4615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9797    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840   -0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2069   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227   -0.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.7787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    1.4024    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1NC[C@@H]2C[C@H]1CN1C(=O)C=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c14-10-3-1-2-9-7-4-8(6-13(9)10)11(15)12-5-7/h1-3,7-8H,4-6H2,(H,12,15)/t7-,8-/m0/s1

> <INCHI_KEY>
ITGCPUVLXUYSOK-YUMQZZPRSA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.229

> <EXACT_MASS>
204.089877634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.434118520568788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-diene-6,10-dione

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
-0.7800177153333334

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.318232015759943

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4774525683297068

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
56.999500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-diene-6,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0055134 (11-Oxocytisine)

Download
PDB for NP0055134 (11-Oxocytisine)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.678   1.911   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.788   0.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.513  -0.488   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.623  -2.024   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.128   0.184   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.017   1.720   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.292   2.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.853   2.728   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.696   0.660   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.583  -1.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.120  -0.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.419  -0.083   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.042  -0.772   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       1.309   1.454   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.317   2.618   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

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3D PDB for NP0055134 (11-Oxocytisine)
Download
SMILES for NP0055134 (11-Oxocytisine)
O=C1NC[C@@H]2C[C@H]1CN1C(=O)C=CC=C21
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INCHI for NP0055134 (11-Oxocytisine)
InChI=1S/C11H12N2O2/c14-10-3-1-2-9-7-4-8(6-13(9)10)11(15)12-5-7/h1-3,7-8H,4-6H2,(H,12,15)/t7-,8-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H12N2O2
Average Mass204.2290 Da
Monoisotopic Mass204.08988 Da
IUPAC Name(1S,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-diene-6,10-dione
Traditional Name(1S,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-diene-6,10-dione
CAS Registry NumberNot Available
SMILES
O=C1NC[C@@H]2C[C@H]1CN1C(=O)C=CC=C21
InChI Identifier
InChI=1S/C11H12N2O2/c14-10-3-1-2-9-7-4-8(6-13(9)10)11(15)12-5-7/h1-3,7-8H,4-6H2,(H,12,15)/t7-,8-/m0/s1
InChI KeyITGCPUVLXUYSOK-YUMQZZPRSA-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
Sophora secundifloraPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassLupin alkaloids  
Sub ClassCytisine and derivatives  
Direct ParentCytisine and derivatives  
Alternative Parents
Substituents
  • Cytisine
    • 

  • Delta-lactam
    • 

  • Piperidinone
    • 

  • Pyridinone
    • 

  • Pyridine
    • 

  • Piperidine
    • 

  • Heteroaromatic compound
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP0.32ALOGPS
logP-0.78ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity57 m³·mol⁻¹ChemAxon
Polarizability20.43 ųChemAxon
Number of Rings3ChemAxon
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 ID13082760  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15939875  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available