17-cyclobutylmethyl-4-methoxy-12-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-trien-13-one

ID: ALA606777

PubChem CID: 46877959

Max Phase: Preclinical

Molecular Formula: C23H31NO2

Molecular Weight: 353.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)[C@]13CCN(CC4CCC4)[C@H](C2)[C@H]1CC(C)C(=O)C3

Standard InChI:  InChI=1S/C23H31NO2/c1-15-10-20-21-11-17-6-7-18(26-2)12-19(17)23(20,13-22(15)25)8-9-24(21)14-16-4-3-5-16/h6-7,12,15-16,20-21H,3-5,8-11,13-14H2,1-2H3/t15?,20-,21-,23-/m1/s1

Standard InChI Key:  JKRWGJJCQQNKLV-CEUCIZKZSA-N

Molfile:  

     RDKit          2D

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    2.2292   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -2.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -5.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -3.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -2.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -2.9273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5646   -1.8431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 13  1  0
  5  1  1  0
  1  6  1  1
  7  5  1  0
  8  7  1  0
  9  2  1  0
 10  6  1  0
  1 11  1  0
 12 10  1  0
 13 11  1  0
 14  4  1  0
 15  5  2  0
 16 10  2  0
 17  7  2  0
 18 15  1  0
 19 18  2  0
 20 14  1  0
 21 18  1  0
 22 25  1  0
 23 12  1  0
 24 20  1  0
 25 20  1  0
 26 21  1  0
  2 27  1  6
  3  4  1  0
  9 12  1  0
  8  3  1  0
 19 17  1  0
 22 24  1  0
  3 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606777

   (1S,9R,10S)-17-(cyclobutylmethyl)-4-methoxy-12-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one

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: 353.51

Molecular Weight (Monoisotopic): 353.2355

AlogP: 3.98

#Rotatable Bonds: 3

Polar Surface Area: 29.54

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.90

CX LogP: 4.08

CX LogD: 1.63

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: 1.10

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