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Showing NP-Card for Dihydrocinchonine (NP0046874)

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Record Information
Version2.0
Created at2022-03-17 20:30:57 UTC
Updated at2022-03-17 20:30:57 UTC
NP-MRD IDNP0046874
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrocinchonine
Description Dihydrocinchonine is found in Anthocephalus chinensis L. and Olea europea L. .
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046874 (Dihydrocinchonine)


  Mrv0541 02241221462D          

 22 25  0  0  1  0            999 V2000
    2.3306    1.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601    0.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    0.3592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9242    1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111    0.3308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258   -0.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727   -0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    0.7145   -0.4125    0.0000 C   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
    0.7145    1.2375    0.0000 C   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
    2.1904    0.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 16 21  1  0  0  0  0
 11 22  1  6  0  0  0
M  END
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3D MOL for NP0046874 (Dihydrocinchonine)

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3D SDF for NP0046874 (Dihydrocinchonine)

  Mrv0541 02241221462D          

 22 25  0  0  1  0            999 V2000
    2.3306    1.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601    0.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    0.3592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9242    1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111    0.3308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258   -0.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727   -0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    0.7145   -0.4125    0.0000 C   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
    0.7145    1.2375    0.0000 C   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
    2.1904    0.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 16 21  1  0  0  0  0
 11 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0046874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC1C[C@@H]2[C@@H](O)C1=CC=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3/t13-,14?,18+,19-/m0/s1

> <INCHI_KEY>
WFJNHVWTKZUUTR-FGVBSWQGSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.4067

> <EXACT_MASS>
296.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.9177370118895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.975123202666667

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.877400317939916

> <JCHEM_PKA_STRONGEST_BASIC>
9.276425230093475

> <JCHEM_POLAR_SURFACE_AREA>
36.36

> <JCHEM_REFRACTIVITY>
88.18630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046874 (Dihydrocinchonine)
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PDB for NP0046874 (Dihydrocinchonine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.350   1.948   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.152   0.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.692   0.671   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.325   1.978   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.047   0.617   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.701   0.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.008  -1.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.416  -0.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.349  -1.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.089   0.905   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   16                                                  
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

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3D PDB for NP0046874 (Dihydrocinchonine)
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SMILES for NP0046874 (Dihydrocinchonine)
CC[C@H]1CN2CCC1C[C@@H]2[C@@H](O)C1=CC=NC2=CC=CC=C12
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INCHI for NP0046874 (Dihydrocinchonine)
InChI=1S/C19H24N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3/t13-,14?,18+,19-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H24N2O
Average Mass296.4067 Da
Monoisotopic Mass296.18886 Da
IUPAC Name(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
Traditional Name(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
CAS Registry NumberNot Available
SMILES
CC[C@H]1CN2CCC1C[C@@H]2[C@@H](O)C1=CC=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C19H24N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3/t13-,14?,18+,19-/m0/s1
InChI KeyWFJNHVWTKZUUTR-FGVBSWQGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anthocephalus chinensis L.Plant
Olea europaeaFooDB
Olea europea L.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassCinchona alkaloids  
Sub ClassNot Available
Direct ParentCinchona alkaloids  
Alternative Parents
Substituents
  • Cinchonan-skeleton
    • 

  • 4-quinolinemethanol
    • 

  • Quinoline
    • 

  • Quinuclidine
    • 

  • Aralkylamine
    • 

  • Piperidine
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • 1,2-aminoalcohol
    • 

  • Secondary alcohol
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Aromatic alcohol
    • 

  • 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
logP3.26ALOGPS
logP2.98ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area36.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.19 m³·mol⁻¹ChemAxon
Polarizability33.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006314  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16212907  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available