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

ID: ALA4789005

PubChem CID: 118560973

Max Phase: Preclinical

Molecular Formula: C20H28N2O2

Molecular Weight: 328.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1OC2(CCN(CCc3ccccc3)CC2)CN(C2CC2)C1=O

Standard InChI:  InChI=1S/C20H28N2O2/c1-16-19(23)22(18-7-8-18)15-20(24-16)10-13-21(14-11-20)12-9-17-5-3-2-4-6-17/h2-6,16,18H,7-15H2,1H3/t16-/m1/s1

Standard InChI Key:  BZPKTOXVMUIFBK-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

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   27.8258  -10.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8216  -11.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5234  -11.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2338  -11.0557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2379  -10.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5316   -9.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4184   -9.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4184  -10.2314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1237  -10.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8289   -9.4142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1237   -9.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1237   -8.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7095   -9.0077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9388  -11.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6491  -11.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3542  -11.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3465  -12.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0508  -12.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7621  -12.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7647  -11.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0599  -11.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7122  -10.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8997  -10.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3098  -11.3514    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
 23 22  1  0
 24 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4789005

   (2R)-4-cyclopropyl-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: 328.46

Molecular Weight (Monoisotopic): 328.2151

AlogP: 2.47

#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: 2.07

CX LogD: 0.47

Aromatic Rings: 1

Heavy Atoms: 24

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