NP-MRD: Showing NP-Card for ( )-chloroquine (NP0318604)

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Record Information

Version

1.0

Created at

2022-09-11 19:12:02 UTC

Updated at

2022-09-11 19:12:02 UTC

NP-MRD ID

NP0318604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

( )-chloroquine

Description

(S)-chloroquine belongs to the class of organic compounds known as 4-aminoquinolines. ( )-chloroquine is found in Alkanna orientalis. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system (S)-chloroquine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
   -5.0529    1.8765   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7629    0.6178   -1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -0.3147   -0.3473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060   -1.2399    0.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6999   -0.7572    1.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636    0.0534   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825    0.1219   -1.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.5393   -1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251   -0.2957   -0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2036   -0.4736    1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8754    0.2671   -0.4474 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.4667   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624   -1.7855    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9712   -2.4915    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1909   -1.9469    0.7561 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3928   -0.6877    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6702   -0.1790    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8498    1.1149   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4308    1.8704   -0.1511 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7745    1.8866   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829    1.3487   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0614   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1555    2.0373   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6186    2.7500   -0.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6403    1.8725    0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2963    0.9284   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7071    0.1080   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7994   -2.1196    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4356   -1.6682    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8808   -1.6843    2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801   -0.3108    2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5607   -0.1129    2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549    0.9711    0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573   -0.8316    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -0.9027   -1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    0.7507   -2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.7875   -2.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717    1.5771   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693   -1.3369   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    0.3082    1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1634   -1.4811    1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508   -0.3713    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    1.2243   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -2.2187    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -3.5150    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5366   -0.7569    0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9116    2.8937   -0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752    1.9815   -0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  9 11  1  0
 11 12  1  0
 12 22  2  0
 22 21  1  0
 21 20  2  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 16 22  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
  8 37  1  0
  8 38  1  0
  7 35  1  0
  7 36  1  0
  6 33  1  0
  6 34  1  0
  2 26  1  0
  2 27  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
 11 43  1  0
 21 48  1  0
 20 47  1  0
 17 46  1  0
 14 45  1  0
 13 44  1  0
M  END


  Mrv0541 05031419102D          

 23 24  0  0  1  0            999 V2000
   -5.3670    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5569    1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9242    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362   -1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3039   -2.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2066    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163   -0.1559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4643   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8440   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0339   -0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -1.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744   -0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -1.8709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168    0.7796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -0.3118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 14  3  1  1  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 20 11  1  0  0  0  0
 20 18  2  0  0  0  0
 21 14  1  0  0  0  0
 21 17  1  0  0  0  0
 22  4  1  0  0  0  0
 22  5  1  0  0  0  0
 22 12  1  0  0  0  0
 14 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0318604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](C)(CCCN(CC)CC)NC1=C2C=CC(Cl)=CC2=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)/t14-/m0/s1

> <INCHI_KEY>
WHTVZRBIWZFKQO-AWEZNQCLSA-N

> <FORMULA>
C18H26ClN3

> <MOLECULAR_WEIGHT>
319.872

> <EXACT_MASS>
319.181525554

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.293845803869125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-N-[(2S)-5-(diethylamino)pentan-2-yl]quinolin-4-amine

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
3.933881141333334

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.324447273782475

> <JCHEM_POLAR_SURFACE_AREA>
28.160000000000004

> <JCHEM_REFRACTIVITY>
96.42299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-N-[(2S)-5-(diethylamino)pentan-2-yl]quinolin-4-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   14                                                            
CONECT    4    1   22                                                       
CONECT    5    2   22                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8    9   15                                                       
CONECT    9    8   16                                                       
CONECT   10   11   17                                                       
CONECT   11   10   20                                                       
CONECT   12    6   22                                                       
CONECT   13   15   18                                                       
CONECT   14    3    7   21   23                                             
CONECT   15    8   13   19                                                  
CONECT   16    9   17   18                                                  
CONECT   17   10   16   21                                                  
CONECT   18   13   16   20                                                  
CONECT   19   15                                                            
CONECT   20   11   18                                                       
CONECT   21   14   17                                                       
CONECT   22    4    5   12                                                  
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(+)-Chloroquine	ChEBI
(+)-N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine	ChEBI

Chemical Formula

C₁₈H₂₆ClN₃

Average Mass

319.8720 Da

Monoisotopic Mass

319.18153 Da

IUPAC Name

7-chloro-N-[(2S)-5-(diethylamino)pentan-2-yl]quinolin-4-amine

Traditional Name

7-chloro-N-[(2S)-5-(diethylamino)pentan-2-yl]quinolin-4-amine

CAS Registry Number

Not Available

SMILES

[H][C@](C)(CCCN(CC)CC)NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)/t14-/m0/s1

InChI Key

WHTVZRBIWZFKQO-AWEZNQCLSA-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
Alkanna orientalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

4-aminoquinolines

Alternative Parents

Substituents

4-aminoquinoline
Haloquinoline
Chloroquinoline
Aminopyridine
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Secondary amine
Amine
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chloroquine (CHEBI:39254 )

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	5.28	ALOGPS
logP	3.93	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	10.32	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.16 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	96.42 m³·mol⁻¹	ChemAxon
Polarizability	37.29 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

639540

PDB ID

Not Available

ChEBI ID

39254

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ( )-chloroquine (NP0318604)

MOL for NP0318604 (( )-chloroquine)

3D MOL for NP0318604 (( )-chloroquine)

3D SDF for NP0318604 (( )-chloroquine)

3D-SDF for NP0318604 (( )-chloroquine)

PDB for NP0318604 (( )-chloroquine)

3D PDB for NP0318604 (( )-chloroquine)

SMILES for NP0318604 (( )-chloroquine)

INCHI for NP0318604 (( )-chloroquine)

Structure for NP0318604 (( )-chloroquine)

3D Structure for NP0318604 (( )-chloroquine)