1-(6-(5-Fluoropyridin-2-yl)-2,6-diazaspiro[3.3]heptan-2-yl)-4-(quinolin-5-yl)butan-1-one

ID: ALA4745187

PubChem CID: 162648061

Max Phase: Preclinical

Molecular Formula: C23H23FN4O

Molecular Weight: 390.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCCc1cccc2ncccc12)N1CC2(C1)CN(c1ccc(F)cn1)C2

Standard InChI:  InChI=1S/C23H23FN4O/c24-18-9-10-21(26-12-18)27-13-23(14-27)15-28(16-23)22(29)8-2-5-17-4-1-7-20-19(17)6-3-11-25-20/h1,3-4,6-7,9-12H,2,5,8,13-16H2

Standard InChI Key:  NIKSUQJKLCBBOJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    8.2971  -18.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0854  -18.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2959  -18.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5076  -17.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458  -20.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539  -20.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7635  -20.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7607  -19.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470  -19.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510  -19.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490  -18.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437  -18.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6389  -18.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444  -19.2648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665  -19.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761  -19.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8819  -19.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5915  -19.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2973  -19.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5954  -20.4664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0871  -19.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5046  -18.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0028  -17.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7112  -18.0746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4180  -17.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4178  -16.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7047  -16.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0008  -16.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1246  -16.4379    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  1  1  0
  9  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21  1  1  0
  1 22  1  0
 22 19  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  3 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4745187

   ---

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: 390.46

Molecular Weight (Monoisotopic): 390.1856

AlogP: 3.44

#Rotatable Bonds: 5

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.30

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.33

References

1. Schrader TO,Xiong Y,Lorenzana AO,Broadhead A,Stebbins KJ,Poon MM,Baccei C,Lorrain DS.  (2021)  Discovery of PIPE-359, a Brain-Penetrant, Selective M Receptor Antagonist with Robust Efficacy in Murine MOG-EAE.,  12  (1): [PMID:33488977] [10.1021/acsmedchemlett.0c00626]

Source

Source(1):

• Scientific Literature