NP-MRD: Showing NP-Card for (s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol (NP0291365)

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Record Information

Version

1.0

Created at

2022-09-09 22:25:39 UTC

Updated at

2022-09-09 22:25:39 UTC

NP-MRD ID

NP0291365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

Description

Dihydroquinidine, also known as LCN-834 or lentoquine, 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. (s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol is found in Aspidosperma marcgravianum, Cinchona calisaya and Cinchona pubescens. It was first documented in 2019 (PMID: 31591731). Based on a literature review a significant number of articles have been published on Dihydroquinidine (PMID: 32134169) (PMID: 32123601) (PMID: 32037417) (PMID: 30712817).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -5.6491    0.2403   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7465    0.4170    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -0.4323    0.3801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7141   -0.1460    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990    0.5548    1.3958 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569    1.7306    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.2777   -0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5960   -0.2027   -0.7776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2977   -0.9712   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -0.1339    0.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5781   -0.7893    1.2897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0375   -1.8176    2.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -1.4280    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -2.6533   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840   -3.2823   -0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -2.6467   -1.1321 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -1.4564   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9308   -0.8014   -0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348    0.4792   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601    1.0868    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653    2.3424    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569    3.1799    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9531    0.4074    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7613   -0.8484    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2511   -0.3141   -1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9616    1.2507   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6248   -0.2526   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5227    1.5012    0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3205    0.1521    1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116   -1.5029    0.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.5156    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5652   -1.0844    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    2.2405    0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4842    2.4489    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1464    1.8300   -1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665    1.3994   -1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074   -0.6248   -1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -1.1581   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -1.8974    0.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    0.7010   -0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -0.1579    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576   -2.6450    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3952   -3.1763   -0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0984   -4.2622   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951   -1.2684   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0710    0.9541   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    3.7713   -0.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961    2.6443    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5005    3.9179    1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2227    0.9106    1.1957 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 24  1  0
 24 23  2  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
  8  3  1  0
 14 13  2  0
 10  5  1  0
 17 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  1
  4 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  1
 12 42  1  0
 23 50  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 19 46  1  0
 18 45  1  0
 15 44  1  0
 14 43  1  0
M  END


  Mrv1652309102200252D          

 24 27  0  0  1  0            999 V2000
    3.1464   -2.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -1.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -0.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -1.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -1.8166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2898   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898   -0.5791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0043   -0.1666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7187   -0.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0043    0.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0043    2.3084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7187    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4332    2.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1477    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1477    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8621    0.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5766    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4332    0.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7187    1.0709    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  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
  8  7  1  6  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  6  0  0  0
 11 13  1  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  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 23 24  1  0  0  0  0
 13 24  2  0  0  0  0
 17 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CC[C@H]1C[C@@H]2[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13?,14-,19+,20-/m0/s1

> <INCHI_KEY>
LJOQGZACKSYWCH-HAOVMRFASA-N

> <FORMULA>
C20H26N2O2

> <MOLECULAR_WEIGHT>
326.44

> <EXACT_MASS>
326.199428085

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.84852155238168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(S)-[(2R,4S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

> <JCHEM_LOGP>
2.817451937000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.892120589819111

> <JCHEM_PKA_STRONGEST_BASIC>
9.176454721982065

> <JCHEM_POLAR_SURFACE_AREA>
45.59

> <JCHEM_REFRACTIVITY>
94.64950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(S)-[(2R,4S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.873  -4.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.873  -3.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.207  -2.621   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.207  -1.081   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.541  -0.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.797  -1.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.797  -2.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.541  -3.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.874  -2.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.874  -1.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.208  -0.311   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.542  -1.081   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.208   1.229   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.874   1.999   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.874   3.539   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      11.208   4.309   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      12.542   3.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.875   4.309   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.209   3.539   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.209   1.999   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.543   1.229   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      17.876   1.999   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.875   1.229   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.542   1.999   0.000  0.00  0.00           C+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   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
LCN-834	MeSH
Lentoquine	MeSH
Hydroquinidine hydrochloride	MeSH
Sérécor	MeSH
Hydroquinidine monosulfate, (1beta,3alpha,4beta,9S)-isomer	MeSH
Hydroquinidine, (1beta,3alpha,4beta,9S)-isomer	MeSH
Hydroquinidine, (8alpha,9R)-isomer	MeSH
Hydroquinidine, (9R)-isomer	MeSH
Hydroquinidine, (9S)-(+-)-isomer	MeSH
Hydroquinidine, (+-)-isomer	MeSH
Hydroquinidine, (1beta,4beta,9S)-(+-)-isomer	MeSH
Hydroquinidine, (8alpha,9S)-isomer	MeSH
Hydroquinine	MeSH
LCN 834	MeSH
Dihydroquinine	MeSH
Hydroquinidine dihydrochloride, (1beta,4beta,3S)-(+-)-isomer	MeSH
Hydroquinidine monosulfate, (1beta,3alpha,4beta,8alpha,9R)-isomer	MeSH
Hydroquinidine sulfate	MeSH
Hydroquinidine sulfate, (9S)-isomer	MeSH
Hydroquinidine, (1beta, 3alpha,4beta,8alpha,9R)-isomer	MeSH
Hydroquinidine	MeSH
Hydroquinidine dihydrochloride, (3alpha,9S)-(+-)-isomer	MeSH
Hydroquinidine monosulfate	MeSH
Hydroquinidine, (3alpha,9S)-(+-)-isomer	MeSH

Chemical Formula

C₂₀H₂₆N₂O₂

Average Mass

326.4400 Da

Monoisotopic Mass

326.19943 Da

IUPAC Name

(S)-[(2R,4S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

Traditional Name

(S)-[(2R,4S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

CAS Registry Number

Not Available

SMILES

CCC1CN2CC[C@H]1C[C@@H]2[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1

InChI Identifier

InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13?,14-,19+,20-/m0/s1

InChI Key

LJOQGZACKSYWCH-HAOVMRFASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspidosperma marcgravianum	LOTUS Database	35616633
Cinchona calisaya	LOTUS Database	35616633
Cinchona pubescens	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cinchona alkaloids

Sub Class

Not Available

Direct Parent

Cinchona alkaloids

Alternative Parents

Substituents

Cinchonan-skeleton
4-quinolinemethanol
Quinoline
Anisole
Phenol ether
Quinuclidine
Alkyl aryl ether
Aralkylamine
Benzenoid
Pyridine
Piperidine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Organoheterocyclic compound
Azacycle
Ether
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.82	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.65 m³·mol⁻¹	ChemAxon
Polarizability	36.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9820301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydroquinidine

METLIN ID

Not Available

PubChem Compound

11645562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Che Z, Yang J, Sun D, Tian Y, Liu S, Lin X, Jiang J, Chen G: Synthesis of Novel (9S)-Acyloxy Derivatives of Quinidine and Dihydroquinidine as Insecticidal Agents. Chem Biodivers. 2020 Apr;17(4):e1900696. doi: 10.1002/cbdv.201900696. Epub 2020 Mar 30. [PubMed:32134169 ]
Xu D, Sanchez-Lopez E, Wang Q, Jiang Z, Marina ML: Determination of l-norvaline and l-tryptophan in dietary supplements by nano-LC using an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column. J Pharm Anal. 2020 Feb;10(1):70-77. doi: 10.1016/j.jpha.2019.10.001. Epub 2019 Oct 23. [PubMed:32123601 ]
Zhao MX, Xiang J, Zhao ZQ, Zhao XL, Shi M: Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of alpha-isocyanoacetates with para-quinone methides. Org Biomol Chem. 2020 Feb 26;18(8):1637-1646. doi: 10.1039/c9ob02652e. [PubMed:32037417 ]
Liu S, Fu X, Loffler R, Lammerhofer M: In-situ photopolymerized polyhedral oligomeric silsesquioxane-derived monolithic capillary columns with quinidine functionality for enantioseparation by nano-liquid chromatography. Electrophoresis. 2019 Dec;40(23-24):3132-3139. doi: 10.1002/elps.201900316. Epub 2019 Oct 15. [PubMed:31591731 ]
Xu D, Wang Q, Sanchez-Lopez E, Jiang Z, Marina ML: Preparation of an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column for the enantioseparation of amino acids by nano-liquid chromatography. J Chromatogr A. 2019 May 24;1593:63-72. doi: 10.1016/j.chroma.2019.01.065. Epub 2019 Jan 24. [PubMed:30712817 ]
LOTUS database [Link]

Showing NP-Card for (s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol (NP0291365)

MOL for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

3D MOL for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

3D SDF for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

3D-SDF for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

PDB for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

3D PDB for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

SMILES for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

INCHI for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

Structure for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)

3D Structure for NP0291365 ((s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol)