NP-MRD: Showing NP-Card for Quinine hydrochloride (NP0333816)

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Record Information

Version

2.0

Created at

2024-09-09 20:40:27 UTC

Updated at

2024-09-09 20:40:27 UTC

NP-MRD ID

NP0333816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinine hydrochloride

Description

Bitter flavouring It is used in tonics and bitter drinks Quinine is a natural white crystalline alkaloid having antipyretic, antimalarial, analgesic, anti-inflammatory properties and a bitter taste. It is a stereoisomer of quinidine which, unlike quinine, is an anti-arrhythmic. Though it has been synthesized in the lab, the bark of the cinchona tree is the only known natural source of quinine. Quinine was the first effective treatment for malaria caused by Plasmodium falciparum, appearing in therapeutics in the 17th century. It remained the antimalarial drug of choice until the 1940s, when other drugs replaced it.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131513252D          

 29 31  0  0  1  0            999 V2000
   -3.5311   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502   -0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022   -0.8839    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3877   -1.2964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1846    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733   -0.0589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0412    0.3536    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1846   -0.8839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3877    0.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    1.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846    2.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167   -0.4714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3877   -2.1214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733    0.7661    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412   -0.4714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  5  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 13  3  1  1  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  2  0  0  0  0
 16  6  1  0  0  0  0
 17 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18  5  1  0  0  0  0
 18 17  1  0  0  0  0
 19 10  1  0  0  0  0
 20 16  1  0  0  0  0
 19 20  1  6  0  0  0
 21  8  1  0  0  0  0
 21 18  2  0  0  0  0
 22  9  1  0  0  0  0
 22 12  1  0  0  0  0
 22 19  1  0  0  0  0
 20 23  1  1  0  0  0
 24  2  1  0  0  0  0
 24 15  1  0  0  0  0
 13 26  1  6  0  0  0
 14 27  1  6  0  0  0
 19 28  1  1  0  0  0
 20 29  1  1  0  0  0
M  END


  Mrv1533007131513252D          

 29 31  0  0  1  0            999 V2000
   -3.5311   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502   -0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022   -0.8839    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3877   -1.2964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1846    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733   -0.0589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0412    0.3536    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1846   -0.8839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3877    0.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    1.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846    2.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167   -0.4714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3877   -2.1214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733    0.7661    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412   -0.4714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  5  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 13  3  1  1  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  2  0  0  0  0
 16  6  1  0  0  0  0
 17 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18  5  1  0  0  0  0
 18 17  1  0  0  0  0
 19 10  1  0  0  0  0
 20 16  1  0  0  0  0
 19 20  1  6  0  0  0
 21  8  1  0  0  0  0
 21 18  2  0  0  0  0
 22  9  1  0  0  0  0
 22 12  1  0  0  0  0
 22 19  1  0  0  0  0
 20 23  1  1  0  0  0
 24  2  1  0  0  0  0
 24 15  1  0  0  0  0
 13 26  1  6  0  0  0
 14 27  1  6  0  0  0
 19 28  1  1  0  0  0
 20 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
Cl.[H][C@@](O)(C1=C2C=C(OC)C=CC2=NC=C1)[C@]1([H])C[C@]2([H])CCN1C[C@]2([H])C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O2.ClH/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;1H/t13-,14-,19-,20+;/m0./s1

> <INCHI_KEY>
LBSFSRMTJJPTCW-DSXUQNDKSA-N

> <FORMULA>
C20H25ClN2O2

> <MOLECULAR_WEIGHT>
360.88

> <EXACT_MASS>
360.1604558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.05631780212653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.513463950666668

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.892048067691277

> <JCHEM_PKA_STRONGEST_BASIC>
9.045547511829293

> <JCHEM_POLAR_SURFACE_AREA>
45.59

> <JCHEM_REFRACTIVITY>
94.69359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quinine hydrochloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -6.591  -1.650   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.744   5.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.258  -2.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.412   2.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.412   0.660   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.411  -1.650   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.334  -1.393   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.744  -2.420   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.334  -0.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.257  -1.650   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.744   2.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.924  -0.110   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.924  -1.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.590  -2.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.078   2.970   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.411  -0.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.744   0.660   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.078  -0.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.257  -0.110   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.077   0.660   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.078  -1.650   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -2.590   0.660   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       0.077   2.200   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.078   4.510   0.000  0.00  0.00           O+0
HETATM   25 Cl   UNK     0       9.152   0.000   0.000  0.00  0.00          Cl+0
HETATM   26  H   UNK     0      -5.258  -0.880   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.590  -3.960   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.257   1.430   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.077  -0.880   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   24                                                            
CONECT    3    1   13                                                       
CONECT    4    5   15                                                       
CONECT    5    4   18                                                       
CONECT    6    8   16                                                       
CONECT    7    9   14                                                       
CONECT    8    6   21                                                       
CONECT    9    7   22                                                       
CONECT   10   14   19                                                       
CONECT   11   15   17                                                       
CONECT   12   13   22                                                       
CONECT   13    3   12   14   26                                             
CONECT   14    7   10   13   27                                             
CONECT   15    4   11   24                                                  
CONECT   16    6   17   20                                                  
CONECT   17   11   16   18                                                  
CONECT   18    5   17   21                                                  
CONECT   19   10   20   22   28                                             
CONECT   20   16   19   23   29                                             
CONECT   21    8   18                                                       
CONECT   22    9   12   19                                                  
CONECT   23   20                                                            
CONECT   24    2   15                                                       
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
Surquina	MeSH
Aventis brand OF quinine bisulfate	MeSH
Innotech brand OF quinine hydrochloride	MeSH
Prosana brand OF quinine bisulfate	MeSH
Quinine	MeSH
Foy brand OF quinine sulfate	MeSH
Lafran brand OF quinine hydrochloride	MeSH
Plough brand OF quinine sulfate	MeSH
Quinine sulfate	MeSH
Quinine sulphate	MeSH
Alphapharm brand OF quinine sulfate	MeSH
Myoquin	MeSH
Odan brand OF quinine sulfate	MeSH
Quindan	MeSH
Quinine hydrochloride	MeSH
Strema	MeSH
Bisulfate, quinine	MeSH
Hoechst brand OF quinine sulfate	MeSH
Hydrochloride, quinine	MeSH
Quinamm	MeSH
Quinbisan	MeSH
Quinbisul	MeSH
Quinimax	MeSH
Sulfate, quinine	MeSH
Biquinate	MeSH
Fawns and mcallan brand OF quinine sulfate	MeSH
Legatrim	MeSH
Quinine bisulfate	MeSH
Quinine lafran	MeSH
Fawns and mcallan brand OF quinine bisulfate	MeSH
Quinine-odan	MeSH
Quinoctal	MeSH
Quinson	MeSH
Quinsul	MeSH
Sulphate, quinine	MeSH

Chemical Formula

C₂₀H₂₅ClN₂O₂

Average Mass

360.8800 Da

Monoisotopic Mass

360.16046 Da

IUPAC Name

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

Traditional Name

quinine hydrochloride

CAS Registry Number

Not Available

SMILES

Cl.[H][C@@](O)(C1=C2C=C(OC)C=CC2=NC=C1)[C@]1([H])C[C@]2([H])CCN1C[C@]2([H])C=C

InChI Identifier

InChI=1S/C20H24N2O2.ClH/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;1H/t13-,14-,19-,20+;/m0./s1

InChI Key

LBSFSRMTJJPTCW-DSXUQNDKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
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
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Hydrochloride
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	2.82	ALOGPS
logP	2.51	ChemAxon
logS	-3	ALOGPS
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	36.06 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

FDB002085

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

91558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Quinine hydrochloride (NP0333816)

MOL for NP0333816 (Quinine hydrochloride)

3D MOL for NP0333816 (Quinine hydrochloride)

3D SDF for NP0333816 (Quinine hydrochloride)

3D-SDF for NP0333816 (Quinine hydrochloride)

PDB for NP0333816 (Quinine hydrochloride)

3D PDB for NP0333816 (Quinine hydrochloride)

SMILES for NP0333816 (Quinine hydrochloride)

INCHI for NP0333816 (Quinine hydrochloride)

Structure for NP0333816 (Quinine hydrochloride)

3D Structure for NP0333816 (Quinine hydrochloride)