NP-MRD: Showing NP-Card for primaquine (NP0262797)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 05:46:47 UTC

Updated at

2022-09-08 05:46:47 UTC

NP-MRD ID

NP0262797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

primaquine

Description

Primaquine, also known as primachin or neo-quipenyl, belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system. Primaquine is a drug which is used for the treatment of malaria. Primaquine is a very strong basic compound (based on its pKa). primaquine is found in Streptomyces rimosus. primaquine was first documented in 1955 (PMID: 13242948). An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position (PMID: 4027117) (PMID: 8828017) (PMID: 16968913).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.6715   -2.8713   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465   -2.2930   -0.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -1.0468   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8352   -0.5246   -0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    0.7071   -0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344    1.3158   -0.7735 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8716    0.7197   -1.5615 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3977    0.2220   -2.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5744   -0.3907   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    0.1465    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -1.0595    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8940   -2.0762    1.4330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941    1.4085    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    2.6167    0.8417 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216    3.3193    1.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481    2.8428    2.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    1.6030    1.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5145    0.8960    0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9287   -0.3411    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9254   -3.7045   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5308   -2.1764   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492   -3.3542    0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979   -1.1077   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219    2.3144   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215    1.5532   -1.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174    0.6979   -3.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    0.5029   -3.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5948   -0.8691   -3.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129   -1.2321   -0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282   -0.7896   -1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695    0.5841    1.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9926    0.8599    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771   -1.4496    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2655   -0.6970    2.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716   -1.6983    2.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948   -2.8874    1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    4.3177    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778    3.4416    2.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3381    1.2222    1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.7221    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 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
 19  3  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
M  END

1087
  Mrv0541 02231215142D          

 19 20  0  0  1  0            999 V2000
    2.8075    2.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.8381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    0.8459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 19  1  0  0  0  0
  2  5  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 18  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3

> <INCHI_KEY>
INDBQLZJXZLFIT-UHFFFAOYSA-N

> <FORMULA>
C15H21N3O

> <MOLECULAR_WEIGHT>
259.3467

> <EXACT_MASS>
259.168462309

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.92487918268025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
1.6429209590000005

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.109150282593124

> <JCHEM_PKA_STRONGEST_BASIC>
10.203764938153093

> <JCHEM_POLAR_SURFACE_AREA>
60.17

> <JCHEM_REFRACTIVITY>
78.51490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1087                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.241   4.713   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.908   0.092   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.907  -5.298   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      10.619   1.579   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574  -0.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.218   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.241  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241   0.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908   1.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -4.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242   2.402   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574   2.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242   3.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574   3.942   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908   4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.619   4.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.014   3.975   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.014   2.370   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.241   6.253   0.000  0.00  0.00           C+0
CONECT    1   14   19                                                       
CONECT    2    5    9                                                       
CONECT    3   10                                                            
CONECT    4   11   18                                                       
CONECT    5    2    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   10                                                       
CONECT    8    5                                                            
CONECT    9    2   11   12                                                  
CONECT   10    3    7                                                       
CONECT   11    4    9   13                                                  
CONECT   12    9   14                                                       
CONECT   13   11   15   16                                                  
CONECT   14    1   12   15                                                  
CONECT   15   13   14                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18    4   17                                                       
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline	ChEBI
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline	ChEBI
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline	ChEBI
Neo-quipenyl	ChEBI
Primachin	ChEBI
Primachinum	ChEBI
Primaquin	ChEBI
Primaquina	ChEBI
Primaquinum	ChEBI
Kanaprim	Kegg
Diphosphate, primaquine	HMDB
Phosphate, primaquine	HMDB
Primacin	HMDB
Boucher and muir brand OF primaquine phosphate	HMDB
Primaquine phosphate	HMDB
Primaquine diphosphate	HMDB

Chemical Formula

C₁₅H₂₁N₃O

Average Mass

259.3467 Da

Monoisotopic Mass

259.16846 Da

IUPAC Name

N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

Traditional Name

N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

CAS Registry Number

Not Available

SMILES

COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

InChI Identifier

InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3

InChI Key

INDBQLZJXZLFIT-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

Species Name	Source	Reference
Streptomyces rimosus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

Aminoquinolines and derivatives

Alternative Parents

Substituents

Aminoquinoline
Methoxyaniline
Anisole
Alkyl aryl ether
Secondary aliphatic/aromatic amine
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Secondary amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:8405 )
N-substituted diamine (CHEBI:8405 )
aminoquinoline (CHEBI:8405 )

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	2.76	ALOGPS
logP	1.64	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.17 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.51 m³·mol⁻¹	ChemAxon
Polarizability	29.92 Å³	ChemAxon
Number of Rings	2	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

HMDB0015219

DrugBank ID

DB01087

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4739

KEGG Compound ID

C07627

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Primaquine

METLIN ID

Not Available

PubChem Compound

4908

PDB ID

Not Available

ChEBI ID

8405

Good Scents ID

Not Available

References

General References

Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. doi: 10.1111/j.1365-2125.1985.tb02709.x. [PubMed:4027117 ]
Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. doi: 10.2165/00002018-199614060-00005. [PubMed:8828017 ]
ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. [PubMed:13242948 ]
Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. [PubMed:16968913 ]
LOTUS database [Link]

Showing NP-Card for primaquine (NP0262797)

MOL for NP0262797 (primaquine)

3D MOL for NP0262797 (primaquine)

3D SDF for NP0262797 (primaquine)

3D-SDF for NP0262797 (primaquine)

PDB for NP0262797 (primaquine)

3D PDB for NP0262797 (primaquine)

SMILES for NP0262797 (primaquine)

INCHI for NP0262797 (primaquine)

Structure for NP0262797 (primaquine)

3D Structure for NP0262797 (primaquine)