trans-8-((4-Aminocyclohexyl)amino)-5-bromo-N-(3-(trifluoromethyl)benzyl)-1,6-naphthyridine-7-carboxamide

ID: ALA2180569

PubChem CID: 45376975

Max Phase: Preclinical

Molecular Formula: C23H23BrF3N5O

Molecular Weight: 522.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H]1CC[C@H](Nc2c(C(=O)NCc3cccc(C(F)(F)F)c3)nc(Br)c3cccnc23)CC1

Standard InChI:  InChI=1S/C23H23BrF3N5O/c24-21-17-5-2-10-29-18(17)19(31-16-8-6-15(28)7-9-16)20(32-21)22(33)30-12-13-3-1-4-14(11-13)23(25,26)27/h1-5,10-11,15-16,31H,6-9,12,28H2,(H,30,33)/t15-,16-

Standard InChI Key:  LEORXJSUBJNFPF-WKILWMFISA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   11.9717  -16.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9705  -17.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6827  -17.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3965  -17.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3937  -16.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6809  -16.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1090  -17.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8202  -17.4330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5326  -17.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2438  -17.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5339  -18.6660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9509  -17.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9433  -16.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2396  -16.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6608  -16.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6579  -17.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3652  -17.8398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0759  -17.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0748  -16.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3669  -16.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9391  -15.3798    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   16.9534  -18.6651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6623  -19.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6607  -19.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3656  -20.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0745  -19.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0740  -19.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3646  -18.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7819  -20.2938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6785  -15.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3850  -14.9753    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9696  -14.9795    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.6706  -14.5650    0.0000 F   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  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 16  1  0
 15 13  1  0
 13 14  2  0
 14 10  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  2  0
 13 21  1  0
 12 22  1  0
 23 22  1  1
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  6
  6 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2180569

   8-[(4-aminocyclohexyl)amino]-5-bromo-N-[[3-(trifluoromethyl)phenyl]methyl]-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: 522.37

Molecular Weight (Monoisotopic): 521.1038

AlogP: 5.02

#Rotatable Bonds: 5

Polar Surface Area: 92.93

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.62

CX Basic pKa: 10.45

CX LogP: 4.38

CX LogD: 1.64

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -1.35

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