N4-(6-methoxy-4-(2-methylbutyl)quinolin-8-yl)pentane-1,4-diamine but-2-enedioic acid

ID: ALA3273116

PubChem CID: 90677970

Max Phase: Preclinical

Molecular Formula: C24H35N3O5

Molecular Weight: 329.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)Cc1ccnc2c(NC(C)CCCN)cc(OC)cc12.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C20H31N3O.C4H4O4/c1-5-14(2)11-16-8-10-22-20-18(16)12-17(24-4)13-19(20)23-15(3)7-6-9-21;5-3(6)1-2-4(7)8/h8,10,12-15,23H,5-7,9,11,21H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  NPPIZQHIQKUWMD-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   33.8075  -12.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5152  -12.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0998  -12.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3921  -12.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3921  -13.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2229  -12.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5152  -11.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6844  -12.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9815  -13.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9804  -14.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6952  -14.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6935  -13.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4088  -13.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4095  -14.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1249  -14.7506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8398  -14.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8351  -13.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1192  -13.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1149  -12.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2670  -13.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2668  -12.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6971  -15.5817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4125  -15.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4145  -16.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1261  -15.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8415  -15.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5550  -15.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2704  -15.9859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8271  -11.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8228  -11.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5350  -10.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5438  -12.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  3  4  1  0
  4  5  2  0
  2  6  2  0
  2  7  1  0
  4  8  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
  9 20  1  0
 20 21  1  0
 11 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 19 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 329.49

Molecular Weight (Monoisotopic): 329.2467

AlogP: 4.37

#Rotatable Bonds: 9

Polar Surface Area: 60.17

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.20

CX LogP: 3.78

CX LogD: 1.17

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.03

References

1. Carroll FI, Berrang BD, Linn CP..  (1979)  Synthesis of 4-alkyl and 4-(beta-alkylvinyl) derivatives of primaquine as potential antimalarials.,  22  (11): [PMID:118257] [10.1021/jm00197a016]

Source

Source(1):

• Scientific Literature