(1R,5R,9S)-(-)-5-(3-Hydroxyphenyl)-2-(4-(trifluoromethyl)phenethyl)-2-azabicyclo[3.3.1]nonan-9-ol hydrochloride

ID: ALA4102551

PubChem CID: 137657690

Max Phase: Preclinical

Molecular Formula: C23H27ClF3NO2

Molecular Weight: 405.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Oc1cccc([C@]23CCC[C@H]([C@H]2O)N(CCc2ccc(C(F)(F)F)cc2)CC3)c1

Standard InChI:  InChI=1S/C23H26F3NO2.ClH/c24-23(25,26)17-8-6-16(7-9-17)10-13-27-14-12-22(11-2-5-20(27)21(22)29)18-3-1-4-19(28)15-18;/h1,3-4,6-9,15,20-21,28-29H,2,5,10-14H2;1H/t20-,21-,22-;/m1./s1

Standard InChI Key:  AKBZSAUQISOIGO-AFYLVLOISA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    9.9000  -23.1000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5451  -22.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5451  -23.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2587  -23.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9699  -23.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9699  -22.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2587  -22.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354  -22.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326  -21.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145  -20.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021  -21.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105  -22.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188  -22.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094  -20.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2587  -21.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592  -22.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5391  -23.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1061  -22.2462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7642  -21.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5285  -22.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1823  -21.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9411  -21.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5983  -21.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4886  -20.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7231  -20.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0740  -20.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1628  -21.6448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1707  -20.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9631  -20.3604    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0559  -19.1802    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7743  -19.4218    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  2  8  1  6
 10 14  1  0
  7 15  1  6
  2 16  1  0
 16 17  1  0
  6 18  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  6 27  1  1
 24 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.46

Molecular Weight (Monoisotopic): 405.1916

AlogP: 4.51

#Rotatable Bonds: 4

Polar Surface Area: 43.70

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.14

CX Basic pKa: 9.44

CX LogP: 4.46

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.79

Np Likeness Score: 0.29

References

1. Truong PM, Hassan SA, Lee YS, Kopajtic TA, Katz JL, Chadderdon AM, Traynor JR, Deschamps JR, Jacobson AE, Rice KC..  (2017)  Modulation of opioid receptor affinity and efficacy via N-substitution of 9β-hydroxy-5-(3-hydroxyphenyl)morphan: Synthesis and computer simulation study.,  25  (8): [PMID:28314512] [10.1016/j.bmc.2017.02.064]

Source

Source(1):

• Scientific Literature