NP-MRD: Showing NP-Card for epiquinine (NP0214904)

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Record Information

Version

2.0

Created at

2022-09-05 14:19:56 UTC

Updated at

2022-09-05 14:19:56 UTC

NP-MRD ID

NP0214904

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epiquinine

Description

Epiquinine, also known as apo quinidine or quincardine, 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. epiquinine is found in Cinchona pubescens. epiquinine was first documented in 2012 (PMID: 24061297). Based on a literature review a small amount of articles have been published on Epiquinine (PMID: 32214482) (PMID: 28581297) (PMID: 22869567) (PMID: 22276975).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
   -6.2623   -1.0620   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -1.0492   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0226   -0.2350   -0.0797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0090   -1.0701    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -0.2880    0.7266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760    1.0522    1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7749    1.8458    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151    0.7881   -0.9455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0696    0.1993   -1.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1637   -0.4019   -0.5624 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2466    0.0710   -0.6573 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3966    1.4112   -0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -0.7250    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7639   -1.7534    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671   -2.5073    1.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -2.2357    1.6502 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -1.2363    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.9921    0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000    0.0169    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4582    0.7905   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611    1.8199   -1.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336    2.0924   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0952    0.5247   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5415   -0.4687    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6120   -0.4613    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9682   -1.6587   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6542   -1.6552   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5641    0.3634    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3473   -1.3741    1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011   -1.9572    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    1.6072    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8451    0.9634    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591    2.3926    0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0996    2.5533   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9786    1.2171   -1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    1.0649   -2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173   -0.4824   -2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349   -1.5099   -0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824    0.0078   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.5084    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -2.0572    1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -3.3164    2.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4596   -1.5929    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717    0.2194    0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5617    3.0330   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    2.1425   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8626    1.2748   -2.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    1.1302   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 23  2  0
 23 24  1  0
 24 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 19 20  1  0
  5 10  1  0
 17 24  1  0
  3  8  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 11 39  1  6
 12 40  1  0
 10 38  1  6
  9 36  1  0
  9 37  1  0
  8 35  1  6
  7 33  1  0
  7 34  1  0
  6 31  1  0
  6 32  1  0
  4 29  1  0
  4 30  1  0
  3 28  1  1
  2 27  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652309052216192D          

 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  1  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  1  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  2  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
  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  6  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>
NP0214904

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=CN=C2C=C1)[C@H](O)[C@@H]1C[C@@H]2CCN1C[C@@H]2C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O2/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/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20-/m0/s1

> <INCHI_KEY>
LOUPRKONTZGTKE-FEBSWUBLSA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.424

> <EXACT_MASS>
324.183778021

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.918614628375515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.513463950666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.892048067691277

> <JCHEM_PKA_STRONGEST_BASIC>
9.045547511829296

> <JCHEM_POLAR_SURFACE_AREA>
45.59

> <JCHEM_REFRACTIVITY>
94.6936

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-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
Quincardine	MeSH
Sulfate, quinidine	MeSH
Apo quinidine	MeSH
Chinidin	MeSH
Quinidex	MeSH
Quinora	MeSH
Adaquin	MeSH
Apo-quinidine	MeSH
Quinidine	MeSH
Quinidine sulfate	MeSH

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4240 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=CN=C2C=C1)[C@H](O)[C@@H]1C[C@@H]2CCN1C[C@@H]2C=C

InChI Identifier

InChI=1S/C20H24N2O2/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/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20-/m0/s1

InChI Key

LOUPRKONTZGTKE-FEBSWUBLSA-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
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
Quinuclidine
Alkyl aryl ether
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
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	2.51	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.05	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	94.69 m³·mol⁻¹	ChemAxon
Polarizability	35.92 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

8624355

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10448938

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Varro G, Pogranyi B, Grun A, Simon A, Hegedus L, Kadas I: Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety. Monatsh Chem. 2018;149(12):2265-2285. doi: 10.1007/s00706-018-2287-7. Epub 2018 Oct 26. [PubMed:32214482 ]
Varro G, Hegedus L, Simon A, Balogh A, Grun A, Leveles I, Vertessy BG, Kadas I: The First Enantioselective Total Synthesis of (-)-trans-Dihydronarciclasine. J Nat Prod. 2017 Jun 23;80(6):1909-1917. doi: 10.1021/acs.jnatprod.7b00208. Epub 2017 Jun 5. [PubMed:28581297 ]
Maier NM, Greco E, Petrovaj J, Lindner W: Chromatographic Enantiomer Separation Using 9-Amino-9-(deoxy)-epiquinine-derived Chiral Selectors: Control of Chiral Recognition via Introduction of Additional Stereogenic Centers. Acta Chim Slov. 2012 Sep;59(3):454-63. [PubMed:24061297 ]
Griffin CE, Hoke JM, Samarakoon U, Duan J, Mu J, Ferdig MT, Warhurst DC, Cooper RA: Mutation in the Plasmodium falciparum CRT protein determines the stereospecific activity of antimalarial cinchona alkaloids. Antimicrob Agents Chemother. 2012 Oct;56(10):5356-64. doi: 10.1128/AAC.05667-11. Epub 2012 Aug 6. [PubMed:22869567 ]
de Villiers KA, Gildenhuys J, le Roex T: Iron(III) protoporphyrin IX complexes of the antimalarial Cinchona alkaloids quinine and quinidine. ACS Chem Biol. 2012 Apr 20;7(4):666-71. doi: 10.1021/cb200528z. Epub 2012 Feb 3. [PubMed:22276975 ]
LOTUS database [Link]

Showing NP-Card for epiquinine (NP0214904)

MOL for NP0214904 (epiquinine)

3D MOL for NP0214904 (epiquinine)

3D SDF for NP0214904 (epiquinine)

3D-SDF for NP0214904 (epiquinine)

PDB for NP0214904 (epiquinine)

3D PDB for NP0214904 (epiquinine)

SMILES for NP0214904 (epiquinine)

INCHI for NP0214904 (epiquinine)

Structure for NP0214904 (epiquinine)

3D Structure for NP0214904 (epiquinine)