(R)-3-(pyridin-2-ylmethyl)-5-(pyridin-2-ylmethylene)piperidin-4-one

ID: ALA3409837

PubChem CID: 118731938

Max Phase: Preclinical

Molecular Formula: C17H17N3O

Molecular Weight: 279.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccccn2)CNC[C@H]1Cc1ccccn1

Standard InChI:  InChI=1S/C17H17N3O/c21-17-13(9-15-5-1-3-7-19-15)11-18-12-14(17)10-16-6-2-4-8-20-16/h1-9,14,18H,10-12H2/b13-9+/t14-/m1/s1

Standard InChI Key:  OPIYSDPMUYQQAV-KADHNRKRSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -1.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972   -0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920    0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1903    1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939    0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920    0.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903    1.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939    0.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  2  0
  8  9  1  0
  1 10  1  1
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3409837

   ---

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: 279.34

Molecular Weight (Monoisotopic): 279.1372

AlogP: 1.89

#Rotatable Bonds: 3

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.15

CX LogP: 1.64

CX LogD: 1.44

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: -0.59

References

1. Baldwin PR, Reeves AZ, Powell KR, Napier RJ, Swimm AI, Sun A, Giesler K, Bommarius B, Shinnick TM, Snyder JP, Liotta DC, Kalman D..  (2015)  Monocarbonyl analogs of curcumin inhibit growth of antibiotic sensitive and resistant strains of Mycobacterium tuberculosis.,  92  [PMID:25618016] [10.1016/j.ejmech.2015.01.020]

Source

Source(1):

• Scientific Literature