5-(3,6-Diazabicyclo[3.1.1]heptane-3-yl)-N-(3-methoxyphenyl)nicotinamide

ID: ALA4532589

PubChem CID: 155547147

Max Phase: Preclinical

Molecular Formula: C18H20N4O2

Molecular Weight: 324.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(NC(=O)c2cncc(N3CC4CC(C3)N4)c2)c1

Standard InChI:  InChI=1S/C18H20N4O2/c1-24-17-4-2-3-13(7-17)21-18(23)12-5-16(9-19-8-12)22-10-14-6-15(11-22)20-14/h2-5,7-9,14-15,20H,6,10-11H2,1H3,(H,21,23)

Standard InChI Key:  ZLVRFKCBPDMHFZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    3.5823  -26.6732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594  -26.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0378  -26.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354  -26.0588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060  -26.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1800  -25.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2100  -27.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591  -28.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902  -28.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630  -28.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6051  -27.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9814  -26.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0638  -27.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828  -27.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0110  -27.7005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5277  -26.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7843  -27.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4133  -27.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1859  -27.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3316  -26.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6985  -26.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9239  -26.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8414  -25.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6177  -25.2310    0.0000 C   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
 21 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532589

   ---

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: 324.38

Molecular Weight (Monoisotopic): 324.1586

AlogP: 1.89

#Rotatable Bonds: 4

Polar Surface Area: 66.49

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.12

CX LogP: 1.27

CX LogD: -0.44

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.90

Np Likeness Score: -1.33

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