N-(3-(3,9-diazaspiro[5.5]undecane-3-carbonyl)phenyl)acetamide

ID: ALA5177970

PubChem CID: 119047625

Max Phase: Preclinical

Molecular Formula: C18H25N3O2

Molecular Weight: 315.42

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(C(=O)N2CCC3(CCNCC3)CC2)c1

Standard InChI:  InChI=1S/C18H25N3O2/c1-14(22)20-16-4-2-3-15(13-16)17(23)21-11-7-18(8-12-21)5-9-19-10-6-18/h2-4,13,19H,5-12H2,1H3,(H,20,22)

Standard InChI Key:  DCGKLGYFWMHNPR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.8518  -30.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5668  -30.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2788  -30.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2821  -29.5666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5671  -29.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8489  -29.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4259  -30.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4259  -31.2148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1405  -31.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8550  -31.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1405  -29.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9959  -29.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9981  -28.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7062  -29.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7045  -30.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4163  -30.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1303  -30.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1280  -29.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4156  -29.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8395  -29.1479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5536  -29.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2651  -29.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5562  -30.3804    0.0000 O   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
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10  1  1  0
  1 11  1  0
  4 12  1  0
 12 13  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 14  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5177970

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 315.42

Molecular Weight (Monoisotopic): 315.1947

AlogP: 2.25

#Rotatable Bonds: 2

Polar Surface Area: 61.44

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.99

CX Basic pKa: 10.33

CX LogP: 0.81

CX LogD: -1.95

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.88

Np Likeness Score: -1.21

References

1. Bavo F, de-Jong H, Petersen J, Falk-Petersen CB, Löffler R, Sparrow E, Rostrup F, Eliasen JN, Wilhelmsen KS, Barslund K, Bundgaard C, Nielsen B, Kristiansen U, Wellendorph P, Bogdanov Y, Frølund B..  (2021)  Structure-Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect.,  64  (24.0): [PMID:34908407] [10.1021/acs.jmedchem.1c00290]

Source

Source(1):

• Scientific Literature