1,3-Bis(4-((6-methoxyquinolin-8-yl)amino)pentyl)urea

ID: ALA1739045

PubChem CID: 53326072

Max Phase: Preclinical

Molecular Formula: C31H40N6O3

Molecular Weight: 544.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCNC(=O)NCCCC(C)Nc2cc(OC)cc3cccnc23)c2ncccc2c1

Standard InChI:  InChI=1S/C31H40N6O3/c1-21(36-27-19-25(39-3)17-23-11-7-13-32-29(23)27)9-5-15-34-31(38)35-16-6-10-22(2)37-28-20-26(40-4)18-24-12-8-14-33-30(24)28/h7-8,11-14,17-22,36-37H,5-6,9-10,15-16H2,1-4H3,(H2,34,35,38)

Standard InChI Key:  VBDUDTPBEHEYTA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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  -10.3301  -17.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9121  -18.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072    2.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -3.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -5.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8775   -6.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1622   -9.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1205  -10.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  2  3  1  0
  8 11  2  0
 12  9  1  0
  9 10  2  0
 20 23  2  0
 21 22  2  0
 22 25  1  0
 24 23  1  0
 24 25  2  0
 10 11  1  0
 12 13  2  0
  5  6  1  0
  1  2  1  0
  5  7  1  0
  3  4  1  0
 24 29  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
  6  8  1  0
 20 30  1  0
  8 13  1  0
 30 31  1  0
 12 17  1  0
 22 32  1  0
 13 14  1  0
 32 33  1  0
 14 15  2  0
 33 34  1  0
 15 16  1  0
 33 35  1  0
 16 17  2  0
 35 36  1  0
 36 37  1  0
 10 18  1  0
 37 38  1  0
  4  5  1  0
 38 39  1  0
 18 19  1  0
 39 40  2  0
 39  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1739045

   1,3-Bis[4-[(6-methoxyquinolin-8-yl)amino]pentyl]urea

2. Alternative Forms:

   

   ALA1739045

   1,3-Bis[4-[(6-methoxyquinolin-8-yl)amino]pentyl]urea;dihydrochloride

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: 544.70

Molecular Weight (Monoisotopic): 544.3162

AlogP: 5.96

#Rotatable Bonds: 14

Polar Surface Area: 109.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.36

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.15

Np Likeness Score: -0.54

References

1. Pavić K, Perković I, Cindrić M, Pranjić M, Martin-Kleiner I, Kralj M, Schols D, Hadjipavlou-Litina D, Katsori AM, Zorc B..  (2014)  Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: synthesis, cytostatic and antioxidative activity.,  86  [PMID:25203780] [10.1016/j.ejmech.2014.09.013]

2. Levatić J, Pavić K, Perković I, Uzelac L, Ester K, Kralj M, Kaiser M, Rottmann M, Supek F, Zorc B..  (2018)  Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity.,  146  [PMID:29407988] [10.1016/j.ejmech.2018.01.062]

3. Pavić K, Perković I, Pospíšilová Š, Machado M, Fontinha D, Prudêncio M, Jampilek J, Coffey A, Endersen L, Rimac H, Zorc B..  (2018)  Primaquine hybrids as promising antimycobacterial and antimalarial agents.,  143  [PMID:29220797] [10.1016/j.ejmech.2017.11.083]

Source

Source(1):

• Scientific Literature