4-methoxy-11,12,17-trimethyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-triene

ID: ALA606833

PubChem CID: 46877967

Max Phase: Preclinical

Molecular Formula: C20H29NO

Molecular Weight: 299.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)[C@@]13CCC(C)[C@H](C)C1[C@@H](C2)N(C)CC3

Standard InChI:  InChI=1S/C20H29NO/c1-13-7-8-20-9-10-21(3)18(19(20)14(13)2)11-15-5-6-16(22-4)12-17(15)20/h5-6,12-14,18-19H,7-11H2,1-4H3/t13?,14-,18+,19?,20-/m0/s1

Standard InChI Key:  UVAMKQKDNCTETB-BQSCSUPLSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    2.8167   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -2.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -4.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -2.1975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5 11  1  0
  6  7  1  0
  7  4  1  0
  8  2  1  0
  1  9  1  1
 10  1  1  0
 11  9  1  0
 12  4  2  0
 13 15  1  0
 14  7  2  0
 15 10  1  0
 16 12  1  0
 17 16  2  0
 18  5  1  0
 19 16  1  0
  8 20  1  1
 21 13  1  0
 22 19  1  0
 13  8  1  0
  3  5  1  0
  6  3  1  0
 17 14  1  0
  3 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606833

   (1R,9R,11S)-4-methoxy-11,12,17-trimethyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene

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: 299.46

Molecular Weight (Monoisotopic): 299.2249

AlogP: 3.88

#Rotatable Bonds: 1

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.06

CX LogP: 4.07

CX LogD: 1.47

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: 1.36

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