(R)-9-(2,6-difluorophenethyl)-4-ethyl-2-methyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

ID: ALA4756310

PubChem CID: 162655458

Max Phase: Preclinical

Molecular Formula: C19H26F2N2O2

Molecular Weight: 352.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1CC2(CCN(CCc3c(F)cccc3F)CC2)O[C@H](C)C1=O

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

Standard InChI Key:  YOVPWJVEUHXQCZ-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.7451  -17.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410  -18.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4427  -18.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1531  -18.3073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1572  -17.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4510  -17.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377  -16.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377  -17.4829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430  -17.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483  -16.6657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430  -16.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430  -15.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288  -16.2592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8582  -18.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5685  -18.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2735  -18.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2659  -19.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9701  -19.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6814  -19.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6841  -18.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792  -18.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316  -17.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228  -17.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9819  -17.5086    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5549  -19.9504    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
 17 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756310

   ---

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: 7.85

CX LogP: 2.25

CX LogD: 1.67

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.84

Np Likeness Score: -0.63

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