4-cyclobutylmethyl-16-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-10-ol

ID: ALA606776

PubChem CID: 46877958

Max Phase: Preclinical

Molecular Formula: C22H29NO2

Molecular Weight: 339.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CC[C@@H]2Oc3c(O)ccc4c3[C@@]23CCN(CC2CCC2)[C@H](C4)C13

Standard InChI:  InChI=1S/C22H29NO2/c1-13-5-8-18-22-9-10-23(12-14-3-2-4-14)16(19(13)22)11-15-6-7-17(24)21(25-18)20(15)22/h6-7,13-14,16,18-19,24H,2-5,8-12H2,1H3/t13-,16+,18-,19?,22-/m0/s1

Standard InChI Key:  KWLWXFFESXKWNZ-FGZLNACISA-N

Molfile:  

     RDKit          2D

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    1.9292   -4.2375    0.0000 C   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
    2.4667   -3.3375    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
    2.4667   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -4.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -2.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -3.0250    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
    0.3792   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -3.0375    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   -3.3375    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
   -0.1458   -4.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.1250    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
    1.6641   -5.8059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750   -2.3560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  2  2  0
  5  1  1  0
  8  6  1  0
  7 13  1  0
  8  1  1  0
  9  2  1  0
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  1 11  1  1
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 13 11  1  0
 14  7  1  0
 15  5  1  0
 16  9  2  0
 17  8  1  0
 18 16  1  0
 19 17  1  0
 20 12  1  0
 21 14  1  0
 22 25  1  0
 15 23  1  1
 24 21  1  0
 25 21  1  0
  6  4  1  0
  3  7  1  0
 15 19  1  0
 10  9  1  0
 18 12  2  0
 24 22  1  0
  8 26  1  1
  3 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606776

   (4R,5S,7aS,12bS)-3-(cyclobutylmethyl)-5-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-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: 339.48

Molecular Weight (Monoisotopic): 339.2198

AlogP: 3.87

#Rotatable Bonds: 2

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.94

CX Basic pKa: 10.94

CX LogP: 3.03

CX LogD: 0.96

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: 1.67

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