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

ID: ALA4741494

PubChem CID: 118561095

Max Phase: Preclinical

Molecular Formula: C19H28N2O2

Molecular Weight: 316.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1CC2(CCN(CCc3ccccc3)CC2)O[C@H](C)C1=O

Standard InChI:  InChI=1S/C19H28N2O2/c1-3-21-15-19(23-16(2)18(21)22)10-13-20(14-11-19)12-9-17-7-5-4-6-8-17/h4-8,16H,3,9-15H2,1-2H3/t16-/m1/s1

Standard InChI Key:  NASMRBRQNLMHLZ-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   25.9396  -10.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9355  -11.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6373  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3476  -11.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3517  -10.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6455  -10.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5322   -9.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5322  -10.6730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2375  -11.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9428   -9.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2375   -9.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2375   -8.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8233   -9.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0527  -11.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7630  -11.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4681  -11.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4604  -12.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1646  -13.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8759  -12.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8786  -11.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1737  -11.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8261  -11.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1173  -10.6763    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4741494

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

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: 316.45

Molecular Weight (Monoisotopic): 316.2151

AlogP: 2.33

#Rotatable Bonds: 4

Polar Surface Area: 32.78

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.99

CX LogP: 1.96

CX LogD: 0.36

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: -0.30

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