(R)-9-(2,4-difluorophenethyl)-4-ethyl-2-methyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

ID: ALA4777859

PubChem CID: 162644152

Max Phase: Preclinical

Molecular Formula: C19H26F2N2O2

Molecular Weight: 352.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1CC2(CCN(CCc3ccc(F)cc3F)CC2)O[C@H](C)C1=O

Standard InChI:  InChI=1S/C19H26F2N2O2/c1-3-23-13-19(25-14(2)18(23)24)7-10-22(11-8-19)9-6-15-4-5-16(20)12-17(15)21/h4-5,12,14H,3,6-11,13H2,1-2H3/t14-/m1/s1

Standard InChI Key:  VXCBGIQXMBAMIY-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.2610   -5.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2569   -5.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9586   -6.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6690   -5.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9669   -4.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536   -4.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536   -5.1054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5589   -5.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2642   -4.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5589   -3.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5589   -3.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1447   -3.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741   -6.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0844   -5.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7894   -6.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7818   -7.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4860   -7.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1973   -7.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2000   -6.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4951   -5.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1475   -5.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387   -5.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4978   -5.1310    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9029   -7.5912    0.0000 F   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  1  1  0
  1 10  1  0
 10 11  1  0
 11 12  1  1
  7 13  2  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 22  1  0
 22 23  1  0
 21 24  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777859

   ---

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: 352.43

Molecular Weight (Monoisotopic): 352.1962

AlogP: 2.61

#Rotatable Bonds: 4

Polar Surface Area: 32.78

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.15

CX LogP: 2.25

CX LogD: 1.43

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.84

Np Likeness Score: -0.88

References

1. García M,Virgili M,Alonso M,Alegret C,Farran J,Fernández B,Bordas M,Pascual R,Burgueño J,Vidal-Torres A,Fernández de Henestrosa AR,Ayet E,Merlos M,Vela JM,Plata-Salamán CR,Almansa C.  (2020)  Discovery of EST73502, a Dual μ-Opioid Receptor Agonist and σ Receptor Antagonist Clinical Candidate for the Treatment of Pain.,  63  (24): [PMID:33064947] [10.1021/acs.jmedchem.0c01127]

Source

Source(1):

• Scientific Literature