4-cyclobutylmethyl-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-triene

ID: ALA606832

PubChem CID: 46877966

Max Phase: Preclinical

Molecular Formula: C22H29NO2

Molecular Weight: 339.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c1O[C@H]1CCCC4[C@@H](C2)N(CC2CCC2)CC[C@@]341

Standard InChI:  InChI=1S/C22H29NO2/c1-24-18-9-8-15-12-17-16-6-3-7-19-22(16,20(15)21(18)25-19)10-11-23(17)13-14-4-2-5-14/h8-9,14,16-17,19H,2-7,10-13H2,1H3/t16?,17-,19+,22-/m1/s1

Standard InChI Key:  GZSBGDLKFWEKEP-QFYCEAOBSA-N

Molfile:  

     RDKit          2D

 27 32  0  0  0  0  0  0  0  0999 V2000
    2.1875   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -4.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -2.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -4.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140   -5.8059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5234   -2.3481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  8  4  1  0
  5  1  1  0
  6  5  1  0
  7 13  1  0
  8  1  1  0
  9  2  1  0
 10  6  1  0
  1 11  1  1
 12  3  1  0
 13 11  1  0
 14  7  1  0
 15  9  2  0
 16 15  1  0
 17  5  1  0
 18  8  1  0
 19 12  1  0
 20 14  1  0
 21 18  1  0
 22 24  1  0
 23 20  1  0
 24 20  1  0
 25 19  1  0
  4  3  1  0
  6  7  1  0
 17 21  1  0
 10  9  1  0
 16 12  2  0
 22 23  1  0
  8 26  1  1
  6 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606832

   (4R,7aS,12bS)-3-(cyclobutylmethyl)-9-methoxy-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline

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: 339.48

Molecular Weight (Monoisotopic): 339.2198

AlogP: 3.92

#Rotatable Bonds: 3

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.47

CX LogP: 3.85

CX LogD: 0.91

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.83

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