trans-8-((4-Aminocyclohexyl)amino)-5-bromo-N-cyclohexyl-1,6-naphthyridine-7-carboxamide

ID: ALA2180247

PubChem CID: 71459202

Max Phase: Preclinical

Molecular Formula: C21H28BrN5O

Molecular Weight: 446.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H]1CC[C@H](Nc2c(C(=O)NC3CCCCC3)nc(Br)c3cccnc23)CC1

Standard InChI:  InChI=1S/C21H28BrN5O/c22-20-16-7-4-12-24-17(16)18(25-15-10-8-13(23)9-11-15)19(27-20)21(28)26-14-5-2-1-3-6-14/h4,7,12-15,25H,1-3,5-6,8-11,23H2,(H,26,28)/t13-,15-

Standard InChI Key:  QYZIKQXESFCOBG-CTYIDZIISA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   34.0394  -25.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7505  -24.6433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4630  -25.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1742  -24.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4643  -25.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8813  -25.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8737  -23.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1700  -23.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5911  -23.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5883  -24.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2956  -25.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0063  -24.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0052  -23.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2973  -23.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8695  -22.5901    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   36.8838  -25.8753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5927  -26.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5911  -27.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2960  -27.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0049  -27.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0044  -26.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2950  -25.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7123  -27.5041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3274  -24.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6183  -25.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6168  -25.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3307  -26.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0460  -25.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  2  0
  6 10  1  0
  9  7  1  0
  7  8  2  0
  8  4  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  9  2  0
  7 15  1  0
  6 16  1  0
 17 16  1  1
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  6
  1 24  1  0
  1 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2180247

   8-[(4-aminocyclohexyl)amino]-5-bromo-N-cyclohexyl-1,6-naphthyridine-7-carboxamide

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: 446.39

Molecular Weight (Monoisotopic): 445.1477

AlogP: 4.14

#Rotatable Bonds: 4

Polar Surface Area: 92.93

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.45

CX LogP: 3.58

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.94

References

1. Zeng LF, Wang Y, Kazemi R, Xu S, Xu ZL, Sanchez TW, Yang LM, Debnath B, Odde S, Xie H, Zheng YT, Ding J, Neamati N, Long YQ..  (2012)  Repositioning HIV-1 integrase inhibitors for cancer therapeutics: 1,6-naphthyridine-7-carboxamide as a promising scaffold with drug-like properties.,  55  (22): [PMID:23098137] [10.1021/jm300667v]

Source

Source(1):

• Scientific Literature