NP-MRD: Showing NP-Card for (+)-Dihydrocinchonine (NP0137527)

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Record Information

Version

2.0

Created at

2022-05-30 16:55:08 UTC

Updated at

2022-05-30 16:55:08 UTC

NP-MRD ID

NP0137527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Dihydrocinchonine

Description

Hydrocinchonine, also known as cinchonifine, 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. Hydrocinchonine is a very strong basic compound (based on its pKa). Outside of the human body, Hydrocinchonine has been detected, but not quantified in, fruits. This could make hydrocinchonine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    4.4674    2.0819   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055    1.0570    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1706   -0.0386   -0.2585 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0456    0.5091   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8832   -0.4232   -1.0160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4957   -1.7202   -1.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2402   -2.2886   -0.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630   -1.0935    0.6955 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3732   -0.6137    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.2972    0.2943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0165   -0.6706    0.6043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3423   -0.6812    1.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0535   -0.2448   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -0.5219   -1.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818   -0.3053   -2.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153    0.2009   -2.0899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850    0.4949   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872    1.0801   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6062    1.4282    0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6057    1.2325    1.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051    0.6480    1.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    0.2854    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4166    1.7952   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9408    3.0590   -0.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634    2.3151   -0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345    1.4770    1.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    0.5776    1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9270   -0.4866   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6753    1.4351   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411    0.6822   -2.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -2.4294   -1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2657   -1.4994   -2.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310   -2.8907   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -2.9492    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870   -1.3642    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803   -1.3905    2.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6951    0.3221    1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    0.9144    0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -1.8431    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412   -1.5745    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414   -0.9331   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909   -0.5270   -3.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2572    1.2307   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5411    1.8996    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6702    1.5160    2.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250    0.5442    2.1533 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 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  8  3  1  0
 22 13  1  0
 10  5  1  0
 22 17  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  6
  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  1
 11 39  1  6
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END


  Mrv0541 05061305082D          

 22 25  0  0  0  0            999 V2000
   -4.3830    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759    0.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0811   -0.5252    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
   -2.9832    0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8015    1.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    0.2268    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
    0.0000    0.8250    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    0.8250    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    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    0.9436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  2  0  0  0  0
 16  7  2  0  0  0  0
 16 15  1  0  0  0  0
 17  6  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CCC1CC2C(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

> <INCHI_KEY>
WFJNHVWTKZUUTR-UHFFFAOYSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.4067

> <EXACT_MASS>
296.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.380696560266855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{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>
88.1863

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydrocinchonine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.182   2.662   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.235   1.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.751  -0.980   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.569   0.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.213   0.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.229   3.030   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.710   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.839   0.423   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   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  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -4.357   1.761   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   13                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   15                                                       
CONECT    6    4   17                                                       
CONECT    7    9   16                                                       
CONECT    8   10   14                                                       
CONECT    9    7   20                                                       
CONECT   10    8   21                                                       
CONECT   11   14   18                                                       
CONECT   12   13   21                                                       
CONECT   13    2   12   14                                                  
CONECT   14    8   11   13                                                  
CONECT   15    5   16   17                                                  
CONECT   16    7   15   19                                                  
CONECT   17    6   15   20                                                  
CONECT   18   11   19   21                                                  
CONECT   19   16   18   22                                                  
CONECT   20    9   17                                                       
CONECT   21   10   12   18                                                  
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
(9S)-10,11-Dihydrocinchonan-9-ol	HMDB
(9S)-10,11-Dihydrocinchonan-9-ol, 9ci	HMDB
10,11-Dihydrocinchonine	HMDB
Cinchonifine	HMDB
Cinchotine	HMDB
Pseudocinchonine	HMDB
Y-cinchonine	HMDB

Chemical Formula

C₁₉H₂₄N₂O

Average Mass

296.4067 Da

Monoisotopic Mass

296.18886 Da

IUPAC Name

{5-ethyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol

Traditional Name

hydrocinchonine

CAS Registry Number

Not Available

SMILES

CCC1CN2CCC1CC2C(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

InChI Key

WFJNHVWTKZUUTR-UHFFFAOYSA-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

Not Available

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
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 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	3.26	ALOGPS
logP	2.98	ChemAxon
logS	-3	ALOGPS
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	33.38 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

HMDB0030283

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002118

KNApSAcK ID

Not Available

Chemspider ID

91899

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101711

PDB ID

Not Available

ChEBI ID

115148

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Dihydrocinchonine (NP0137527)

MOL for NP0137527 ((+)-Dihydrocinchonine)

3D MOL for NP0137527 ((+)-Dihydrocinchonine)

3D SDF for NP0137527 ((+)-Dihydrocinchonine)

3D-SDF for NP0137527 ((+)-Dihydrocinchonine)

PDB for NP0137527 ((+)-Dihydrocinchonine)

3D PDB for NP0137527 ((+)-Dihydrocinchonine)

SMILES for NP0137527 ((+)-Dihydrocinchonine)

INCHI for NP0137527 ((+)-Dihydrocinchonine)

Structure for NP0137527 ((+)-Dihydrocinchonine)

3D Structure for NP0137527 ((+)-Dihydrocinchonine)