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Showing NP-Card for Echinopsine (NP0051213)

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Record Information
Version2.0
Created at2022-04-27 22:36:49 UTC
Updated at2022-04-27 22:36:49 UTC
NP-MRD IDNP0051213
Secondary Accession NumbersNone
Natural Product Identification
Common NameEchinopsine
Description1-Methyl-1,4-dihydroquinolin-4-one belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Echinopsine is found in Echinop ritro, Echinops echinatus, Echinops niveus, Echinops ritro, Echinops sphaerocephalus and Echinops spp.. 1-Methyl-1,4-dihydroquinolin-4-one is a moderately basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051213 (Echinopsine)


  Mrv1533004241509102D          

 12 13  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
  7 12  1  0  0  0  0
M  END
Download

3D MOL for NP0051213 (Echinopsine)

     RDKit          3D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.3070   -1.1663    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599   -0.0675    0.0293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707    1.2114   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.2841   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    2.0775   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2775    3.0244   -0.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    0.7726   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347    0.5407   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -0.7510    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7649   -1.8003    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080   -1.5767    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -0.2716    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -1.6649   -0.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016   -1.8450    0.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020   -0.7171    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8485    1.3833   -0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    3.3176   -0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9294    1.3586   -0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.9209    0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1479   -2.7985    0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992   -2.3906    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  2  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  4 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0051213 (Echinopsine)


  Mrv1533004241509102D          

 12 13  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
  7 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=CC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO/c1-11-7-6-10(12)8-4-2-3-5-9(8)11/h2-7H,1H3

> <INCHI_KEY>
CSJAXRKDCCWCSJ-UHFFFAOYSA-N

> <FORMULA>
C10H9NO

> <MOLECULAR_WEIGHT>
159.188

> <EXACT_MASS>
159.068413914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.824852393927607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-1,4-dihydroquinolin-4-one

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
1.7858623503333333

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.77523962376787

> <JCHEM_PKA_STRONGEST_BASIC>
2.221074380927348

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
49.25350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
echinopsine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0051213 (Echinopsine)

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PDB for NP0051213 (Echinopsine)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   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       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0051213 (Echinopsine)
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SMILES for NP0051213 (Echinopsine)
CN1C=CC(=O)C2=CC=CC=C12
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INCHI for NP0051213 (Echinopsine)
InChI=1S/C10H9NO/c1-11-7-6-10(12)8-4-2-3-5-9(8)11/h2-7H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H9NO
Average Mass159.1880 Da
Monoisotopic Mass159.06841 Da
IUPAC Name1-methyl-1,4-dihydroquinolin-4-one
Traditional Nameechinopsine
CAS Registry NumberNot Available
SMILES
CN1C=CC(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO/c1-11-7-6-10(12)8-4-2-3-5-9(8)11/h2-7H,1H3
InChI KeyCSJAXRKDCCWCSJ-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
Echinop ritro-
Echinops echinatusLOTUS Database
Echinops niveusLOTUS Database
Echinops ritroPlant
Echinops sphaerocephalusPlant
Echinops spp.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassQuinolones and derivatives  
Direct ParentHydroquinolones  
Alternative Parents
Substituents
  • Dihydroquinolone
    • 

  • Dihydroquinoline
    • 

  • Benzenoid
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP0.35ALOGPS
logP1.79ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)16.78ChemAxon
pKa (Strongest Basic)2.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.25 m³·mol⁻¹ChemAxon
Polarizability16.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002154  
Chemspider IDNot Available
KEGG Compound IDC10663  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available