6-Chloro-2-((4-morpholinobutyl)amino)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide

ID: ALA4781713

PubChem CID: 162664303

Max Phase: Preclinical

Molecular Formula: C24H34ClN5O2

Molecular Weight: 460.02

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCCN1CCCC1)c1cc(NCCCCN2CCOCC2)nc2ccc(Cl)cc12

Standard InChI:  InChI=1S/C24H34ClN5O2/c25-19-5-6-22-20(17-19)21(24(31)27-8-12-29-10-3-4-11-29)18-23(28-22)26-7-1-2-9-30-13-15-32-16-14-30/h5-6,17-18H,1-4,7-16H2,(H,26,28)(H,27,31)

Standard InChI Key:  QQUMHSGJRQXGAU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.3759  -10.6803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0814  -10.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0825   -9.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3739   -9.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6684   -9.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9598   -9.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2544   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533  -10.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9619  -10.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6674  -10.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3749   -8.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6705   -7.8192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0845   -7.8210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0856   -7.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7952   -6.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7962   -5.7748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4560   -5.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2023   -4.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3851   -4.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1336   -5.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7900  -10.6780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7890  -11.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4975  -11.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4965  -12.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2009  -13.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2019  -15.5829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9074  -15.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9085  -14.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2040  -13.9485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4944  -14.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4934  -15.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5458   -9.0423    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 11 12  2  0
 11 13  1  0
  4 11  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 20  1  0
 15 16  1  0
 13 14  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 26 31  1  0
 25 29  1  0
 21 22  1  0
  2 21  1  0
  7 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781713

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 460.02

Molecular Weight (Monoisotopic): 459.2401

AlogP: 3.24

#Rotatable Bonds: 10

Polar Surface Area: 69.73

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 2.68

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: -1.79

References

1. Baragaña B,Norcross NR,Wilson C,Porzelle A,Hallyburton I,Grimaldi R,Osuna-Cabello M,Norval S,Riley J,Stojanovski L,Simeons FR,Wyatt PG,Delves MJ,Meister S,Duffy S,Avery VM,Winzeler EA,Sinden RE,Wittlin S,Frearson JA,Gray DW,Fairlamb AH,Waterson D,Campbell SF,Willis P,Read KD,Gilbert IH.  (2016)  Discovery of a Quinoline-4-carboxamide Derivative with a Novel Mechanism of Action, Multistage Antimalarial Activity, and Potent in Vivo Efficacy.,  59  (21): [PMID:27631715] [10.1021/acs.jmedchem.6b00723]

Source

Source(1):

• Scientific Literature