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

ID: ALA606780

PubChem CID: 46877962

Max Phase: Preclinical

Molecular Formula: C17H21NO2

Molecular Weight: 271.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@]23c4c5ccc(O)c4O[C@H]2CCCC3[C@H]1C5

Standard InChI:  InChI=1S/C17H21NO2/c1-18-8-7-17-11-3-2-4-14(17)20-16-13(19)6-5-10(15(16)17)9-12(11)18/h5-6,11-12,14,19H,2-4,7-9H2,1H3/t11?,12-,14+,17-/m1/s1

Standard InChI Key:  LNNWVNGFPYWNQE-PRLVFJKXSA-N

Molfile:  

     RDKit          2D

 22 26  0  0  0  0  0  0  0  0999 V2000
    2.6542   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -4.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -2.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -4.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3814   -5.6507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -2.1975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  7  4  1  0
  5  1  1  0
  6  5  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10 13  1  0
  1 11  1  1
 12  3  1  0
 13 11  1  0
 14  8  2  0
 15 14  1  0
 16  5  1  0
 17  7  1  0
 18 12  1  0
 19 10  1  0
 20 17  1  0
  4  3  1  0
  6 10  1  0
 20 16  1  0
  9  8  1  0
 12 15  2  0
  7 21  1  1
  6 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606780

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

Molecule Features

Natural Product: Yes

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: 271.36

Molecular Weight (Monoisotopic): 271.1572

AlogP: 2.45

#Rotatable Bonds: ┄

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: 10.35

CX Basic pKa: 9.38

CX LogP: 2.11

CX LogD: 0.37

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.79

Np Likeness Score: 1.98

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