5-(3,6-Diazabicyclo[3.1.1]heptane-3-yl)-N-(2,4-difluorophenyl)nicotinamide

ID: ALA4556523

PubChem CID: 155556961

Max Phase: Preclinical

Molecular Formula: C17H16F2N4O

Molecular Weight: 330.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(F)cc1F)c1cncc(N2CC3CC(C2)N3)c1

Standard InChI:  InChI=1S/C17H16F2N4O/c18-11-1-2-16(15(19)4-11)22-17(24)10-3-14(7-20-6-10)23-8-12-5-13(9-23)21-12/h1-4,6-7,12-13,21H,5,8-9H2,(H,22,24)

Standard InChI Key:  WHRKMMNRCVIVON-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   17.0189   -9.3493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3935   -9.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4734   -9.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0714   -8.7327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7415   -8.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6169   -8.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6491   -9.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4977  -10.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1269  -11.2159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9026  -10.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0448  -10.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4187   -9.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5003  -10.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8208   -9.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4517  -10.3787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9661   -9.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2276  -10.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8548  -10.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6302  -10.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7760   -9.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1403   -9.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3672   -9.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7079  -11.4419    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.5526   -9.2574    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  5 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 18 23  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556523

   ---

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: 330.34

Molecular Weight (Monoisotopic): 330.1292

AlogP: 2.16

#Rotatable Bonds: 3

Polar Surface Area: 57.26

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.12

CX LogP: 1.71

CX LogD: 0.00

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.91

Np Likeness Score: -1.70

References

1. Murineddu G, Gotti C, Asproni B, Corona P, Martinello K, Plutino S, Fucile S, Temml V, Moretti M, Viani P, Schuster D, Piras S, Deligia F, Pinna GA..  (2019)  Novel N-aryl nicotinamide derivatives: Taking stock on 3,6-diazabicyclo[3.1.1]heptanes as ligands for neuronal acetylcholine receptors.,  180  [PMID:31299587] [10.1016/j.ejmech.2019.06.079]

Source

Source(1):

• Scientific Literature