17-cyclobutylmethyl-11-ethyl-12-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-trien-4-ol

ID: ALA606883

PubChem CID: 46877969

Max Phase: Preclinical

Molecular Formula: C24H35NO

Molecular Weight: 353.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1C(C)CC[C@]23CCN(CC4CCC4)[C@H](Cc4ccc(O)cc42)C13

Standard InChI:  InChI=1S/C24H35NO/c1-3-20-16(2)9-10-24-11-12-25(15-17-5-4-6-17)22(23(20)24)13-18-7-8-19(26)14-21(18)24/h7-8,14,16-17,20,22-23,26H,3-6,9-13,15H2,1-2H3/t16?,20-,22+,23?,24-/m0/s1

Standard InChI Key:  LOXDVVJBFLMGGL-QUDSLZLISA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    1.9417   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -2.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -5.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -4.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -5.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -2.3475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 11  1  0
  5  1  1  0
  6  7  1  0
  7  5  1  0
  8  2  1  0
  1  9  1  1
 10  1  1  0
 11  9  1  0
 12  4  1  0
 13  5  2  0
 14 16  1  0
 15  7  2  0
 16 10  1  0
 17 13  1  0
 18 17  2  0
 19 12  1  0
 20 17  1  0
  8 21  1  1
 22 25  1  0
 23 14  1  0
 24 19  1  0
 25 19  1  0
 26 21  1  0
  8 14  1  0
  3  4  1  0
  6  3  1  0
 18 15  1  0
 22 24  1  0
  3 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606883

   (1R,9R,11S)-17-(cyclobutylmethyl)-11-ethyl-12-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol

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: 353.55

Molecular Weight (Monoisotopic): 353.2719

AlogP: 5.13

#Rotatable Bonds: 3

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.04

CX Basic pKa: 11.27

CX LogP: 4.49

CX LogD: 2.37

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: 1.31

References

1. Hernández-Gallegos Z, Lehmann PA..  (1990)  A Free-Wilson/Fujita-Ban analysis and prediction of the analgesic potency of some 3-hydroxy- and 3-methoxy-N-alkylmorphinan-6-one opioids.,  33  (10): [PMID:2213833] [10.1021/jm00172a021]

Source

Source(1):

• Scientific Literature