NP-MRD: Showing NP-Card for hydrocinchonidine (NP0209130)

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Record Information

Version

2.0

Created at

2022-09-05 06:25:07 UTC

Updated at

2022-09-05 06:25:07 UTC

NP-MRD ID

NP0209130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hydrocinchonidine

Description

Hydrocinchonidine 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. hydrocinchonidine is found in Cinchona calisaya and Cinchona pubescens. Based on a literature review very few articles have been published on Hydrocinchonidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    4.5589   -1.7878    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7871   -1.1575   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2009    0.1521   -0.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4152    0.8398   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.1796   -0.6614 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    2.1106    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099    1.5043    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    0.0677    1.1088 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1447   -0.6608    0.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034   -0.0709   -0.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9129   -0.2699   -0.4570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1222   -0.0370   -1.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961    0.2883    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9924    1.2282    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936    1.7399    1.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2849    1.2944    1.5214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3936    0.3709    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6819   -0.0302    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8997   -0.9843   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8176   -1.5152   -1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5174   -1.0962   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -0.1584   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.5769    0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8644   -2.2278    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1724   -1.0275    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0468   -1.8956   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -0.9992   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0878    0.8297   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    1.7519   -1.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864    0.0875   -2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    2.7833   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002    2.8486    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589    1.4392    2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219    2.0156    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -0.4234    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -0.5751    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4160   -1.7326    0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -0.7722   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785   -1.4100   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3678   -0.4727   -2.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262    1.5796    1.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340    2.4856    2.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5225    0.3935    0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9102   -1.3096   -0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9100   -2.2535   -2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6982   -1.5461   -1.5907 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 22  1  0
 22 21  2  0
 21 20  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 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  1
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  1
  9 36  1  0
  9 37  1  0
 10 38  1  6
 11 39  1  6
 12 40  1  0
 21 46  1  0
 20 45  1  0
 19 44  1  0
 18 43  1  0
 15 42  1  0
 14 41  1  0
M  END


  Mrv1652309052208252D          

 22 25  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  2  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
    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
  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  1  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  2  0  0  0  0
 21 22  1  0  0  0  0
 13 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)C1=C2C=CC=CC2=NC=C1

> <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-KODHJQJWSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.414

> <EXACT_MASS>
296.188863401

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.67104638640641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.975123202666667

> <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

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

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0      13.875   1.229   0.000  0.00  0.00           C+0
HETATM   22  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   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄N₂O

Average Mass

296.4140 Da

Monoisotopic Mass

296.18886 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)C1=C2C=CC=CC2=NC=C1

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-KODHJQJWSA-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 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
Quinuclidine
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Alcohol
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	2.98	ChemAxon
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.19 m³·mol⁻¹	ChemAxon
Polarizability	33.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00026417

Chemspider ID

5290604

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6914728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hydrocinchonidine (NP0209130)

MOL for NP0209130 (hydrocinchonidine)

3D MOL for NP0209130 (hydrocinchonidine)

3D SDF for NP0209130 (hydrocinchonidine)

3D-SDF for NP0209130 (hydrocinchonidine)

PDB for NP0209130 (hydrocinchonidine)

3D PDB for NP0209130 (hydrocinchonidine)

SMILES for NP0209130 (hydrocinchonidine)

INCHI for NP0209130 (hydrocinchonidine)

Structure for NP0209130 (hydrocinchonidine)

3D Structure for NP0209130 (hydrocinchonidine)