6-Anilino-4-{[1-(5-cyanopyridin-2-yl)piperidin-4-yl]amino}nicotinamide

ID: ALA4474752

PubChem CID: 155537151

Max Phase: Preclinical

Molecular Formula: C23H23N7O

Molecular Weight: 413.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(N2CCC(Nc3cc(Nc4ccccc4)ncc3C(N)=O)CC2)nc1

Standard InChI:  InChI=1S/C23H23N7O/c24-13-16-6-7-22(27-14-16)30-10-8-18(9-11-30)28-20-12-21(26-15-19(20)23(25)31)29-17-4-2-1-3-5-17/h1-7,12,14-15,18H,8-11H2,(H2,25,31)(H2,26,28,29)

Standard InChI Key:  DCHOIOVTXGTPJC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   15.9792   -8.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9781   -8.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6861   -9.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3958   -8.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3929   -8.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6843   -7.7713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2714   -7.7717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5638   -8.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8561   -7.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1490   -8.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -8.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8615   -9.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5657   -8.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6859  -10.2258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9781  -10.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2739  -10.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5682  -10.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5638  -11.4456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2712  -11.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9831  -11.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1041   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1054  -10.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8112   -8.9970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8544  -11.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1503  -11.4387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4415  -11.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4377  -12.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1488  -13.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8547  -12.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7332  -13.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0244  -13.4748    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
  1  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  0
 15 14  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  4 21  1  0
 21 22  2  0
 21 23  1  0
 18 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 30 31  3  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474752

   ---

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: 413.49

Molecular Weight (Monoisotopic): 413.1964

AlogP: 3.27

#Rotatable Bonds: 6

Polar Surface Area: 119.96

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.12

CX LogP: 2.91

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -1.90

References

1. Nakajima Y, Aoyama N, Takahashi F, Sasaki H, Hatanaka K, Moritomo A, Inami M, Ito M, Nakamura K, Nakamori F, Inoue T, Shirakami S..  (2016)  Design, synthesis, and evaluation of 4,6-diaminonicotinamide derivatives as novel and potent immunomodulators targeting JAK3.,  24  (19): [PMID:27544589] [10.1016/j.bmc.2016.08.007]

Source

Source(1):

• Scientific Literature