trans-8-(4-Aminocyclohexylamino)-5-bromo-N-(pyridin-2-ylmethyl)-1,6-naphthyridine-7-carboxamide

ID: ALA2180244

PubChem CID: 71459201

Max Phase: Preclinical

Molecular Formula: C21H23BrN6O

Molecular Weight: 455.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H]1CC[C@H](Nc2c(C(=O)NCc3ccccn3)nc(Br)c3cccnc23)CC1

Standard InChI:  InChI=1S/C21H23BrN6O/c22-20-16-5-3-11-25-17(16)18(27-14-8-6-13(23)7-9-14)19(28-20)21(29)26-12-15-4-1-2-10-24-15/h1-5,10-11,13-14,27H,6-9,12,23H2,(H,26,29)/t13-,14-

Standard InChI Key:  VZXIWXPLEIVOLO-HDJSIYSDSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.5026  -23.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5015  -24.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136  -25.1953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274  -24.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9246  -23.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118  -23.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399  -25.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3511  -24.7795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0636  -25.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7748  -24.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0648  -26.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4818  -25.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742  -23.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7706  -23.9589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917  -23.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1888  -24.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8961  -25.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068  -24.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6057  -23.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8978  -23.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4701  -22.7263    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.4843  -26.0115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1933  -26.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917  -27.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8966  -27.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6054  -27.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6049  -26.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8955  -26.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3128  -27.6403    0.0000 N   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
M  END

Alternative Forms

1. Parent:

   

   ALA2180244

   8-[(4-aminocyclohexyl)amino]-5-bromo-N-(pyridin-2-ylmethyl)-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: 455.36

Molecular Weight (Monoisotopic): 454.1117

AlogP: 3.40

#Rotatable Bonds: 5

Polar Surface Area: 105.82

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 10.44

CX LogP: 2.36

CX LogD: -0.38

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.37

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