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

ID: ALA3273113

PubChem CID: 90677967

Max Phase: Preclinical

Molecular Formula: C22H31N3O5

Molecular Weight: 301.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1ccnc2c(NC(C)CCCN)cc(OC)cc12.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C18H27N3O.C4H4O4/c1-4-6-14-8-10-20-18-16(14)11-15(22-3)12-17(18)21-13(2)7-5-9-19;5-3(6)1-2-4(7)8/h8,10-13,21H,4-7,9,19H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  RSRVFDMQKUFXEH-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

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   18.4188  -11.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0032  -11.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2954  -11.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2954  -12.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1266  -11.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4188  -10.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5877  -11.2543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7536  -11.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7524  -12.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4673  -12.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4655  -11.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1810  -11.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1817  -12.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8972  -12.7894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6122  -12.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6074  -11.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8916  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8871  -10.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0390  -11.1428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0388  -10.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4692  -13.6206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1848  -14.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1867  -14.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8983  -13.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6138  -14.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3273  -13.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0429  -14.0249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5994   -9.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5950   -9.0709    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
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: 301.43

Molecular Weight (Monoisotopic): 301.2154

AlogP: 3.74

#Rotatable Bonds: 8

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: 3.05

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: -0.12

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