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

ID: ALA606778

PubChem CID: 46877960

Max Phase: Preclinical

Molecular Formula: C21H27NO2

Molecular Weight: 325.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC[C@@H]2[C@H]3Cc4ccc(O)cc4[C@@]2(CCN3CC2CCC2)C1

Standard InChI:  InChI=1S/C21H27NO2/c23-16-5-4-15-10-20-18-7-6-17(24)12-21(18,19(15)11-16)8-9-22(20)13-14-2-1-3-14/h4-5,11,14,18,20,23H,1-3,6-10,12-13H2/t18-,20-,21+/m1/s1

Standard InChI Key:  BXGAYXHFRRYZPR-NRSPTQNISA-N

Molfile:  

     RDKit          2D

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   -1.3600   -0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2300   -0.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600   -0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3600    1.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300    1.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -2.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600   -0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -2.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974   -0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600    2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    3.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -3.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3600   -3.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600    3.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3600    4.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440   -2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5238    4.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4674   -3.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8648   -2.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -3.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -1.3679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075    0.3596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  4  1  0
  4  1  1  0
  5  1  1  0
  6  5  1  0
  7  6  1  0
  1  8  1  1
  9  1  1  0
 10  4  1  0
 11  8  1  0
 12  2  1  0
 13  5  2  0
 14  9  1  0
 15  6  2  0
 16 14  2  0
 17 14  1  0
 18 13  1  0
 19 18  2  0
 20 12  1  0
 21 18  1  0
 22 24  1  0
 23 20  1  0
 24 20  1  0
  4 25  1  6
  3  2  1  0
 10 17  1  0
  7  3  1  0
 19 15  1  0
 22 23  1  0
  3 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606778

   (1S,9R,10S)-17-(cyclobutylmethyl)-4-hydroxy-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: 325.45

Molecular Weight (Monoisotopic): 325.2042

AlogP: 3.43

#Rotatable Bonds: 2

Polar Surface Area: 40.54

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.36

CX Basic pKa: 10.19

CX LogP: 2.65

CX LogD: 0.99

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.91

Np Likeness Score: 1.17

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