(4-Hydroxyphenyl)(3,9-diazaspiro[5.5]undecan-3-yl)methanone

ID: ALA5202155

PubChem CID: 168292438

Max Phase: Preclinical

Molecular Formula: C16H22N2O2

Molecular Weight: 274.36

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(O)cc1)N1CCC2(CCNCC2)CC1

Standard InChI:  InChI=1S/C16H22N2O2/c19-14-3-1-13(2-4-14)15(20)18-11-7-16(8-12-18)5-9-17-10-6-16/h1-4,17,19H,5-12H2

Standard InChI Key:  ZKUGCZVZAXUEDS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   22.4104  -13.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1254  -13.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8375  -13.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8407  -12.2983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1257  -11.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4075  -12.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9846  -13.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9846  -13.9465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6991  -14.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4136  -13.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6991  -12.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5546  -11.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5568  -11.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2648  -12.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2632  -13.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9750  -13.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6889  -13.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6866  -12.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9742  -11.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4021  -13.5316    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
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202155

   ---

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: 274.36

Molecular Weight (Monoisotopic): 274.1681

AlogP: 2.00

#Rotatable Bonds: 1

Polar Surface Area: 52.57

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.46

CX Basic pKa: 10.34

CX LogP: 0.08

CX LogD: -0.86

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.82

Np Likeness Score: -0.41

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