17-(cyclopropylmethyl)-6alpha-(benzyloxy)-4,5alpha-epoxy-3,14-dihydroxymorphinan

ID: ALA2112730

PubChem CID: 71454481

Max Phase: Preclinical

Molecular Formula: C33H35NO4

Molecular Weight: 509.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc2c3c1OC1[C@H](OCc4ccc(-c5ccccc5)cc4)CCC4(O)C(C2)N(CC2CC2)CCC314

Standard InChI:  InChI=1S/C33H35NO4/c35-26-13-12-25-18-28-33(36)15-14-27(37-20-22-8-10-24(11-9-22)23-4-2-1-3-5-23)31-32(33,29(25)30(26)38-31)16-17-34(28)19-21-6-7-21/h1-5,8-13,21,27-28,31,35-36H,6-7,14-20H2/t27-,28?,31?,32?,33?/m1/s1

Standard InChI Key:  OZBNFFZIMBTLAB-PZEBTOFLSA-N

Molfile:  

     RDKit          2D

 38 45  0  0  0  0  0  0  0  0999 V2000
    9.1152   -5.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4105   -5.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1266   -6.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8886   -5.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8370   -7.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3698   -6.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7058   -5.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9953   -5.8094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4105   -7.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7058   -6.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2902   -5.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2355   -5.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -5.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7480   -5.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8370   -8.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5797   -6.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2734   -4.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745   -3.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8495   -3.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4105   -8.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152   -7.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4527   -4.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1984   -4.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9516   -5.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1266   -8.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9277   -7.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9277   -6.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6902   -7.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2777   -4.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6902   -5.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152   -5.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2777   -6.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5589   -8.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152   -8.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7527   -7.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1652   -8.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9277   -9.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7527   -9.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  6  4  1  0
  7  2  1  0
  8 16  1  0
  9  3  1  0
 10  9  1  0
 11  1  1  0
 12  2  1  0
 13  8  1  0
 14  4  1  0
 15  5  1  0
 16 11  1  0
 17 13  1  0
 18 17  1  0
 19 17  1  0
 20  9  2  0
 21 28  2  0
 14 22  1  1
 23  2  1  0
 24 14  1  0
 25 20  1  0
 26 21  1  0
 27 31  2  0
 28 32  1  0
 29 22  1  0
 30 29  1  0
 31 30  1  0
 32 30  2  0
 33 15  1  0
 34 26  2  0
 35 26  1  0
 36 35  2  0
 37 34  1  0
 38 36  1  0
  5  6  1  0
  8  7  1  0
 24 12  1  0
 10  7  1  0
 15 25  2  0
 18 19  1  0
 21 27  1  0
 38 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2112730

   (7R)-3-(cyclopropylmethyl)-7-[(4-phenylphenyl)methoxy]-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol

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: 509.65

Molecular Weight (Monoisotopic): 509.2566

AlogP: 5.21

#Rotatable Bonds: 6

Polar Surface Area: 62.16

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.30

CX Basic pKa: 9.47

CX LogP: 4.86

CX LogD: 3.06

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.48

Np Likeness Score: 1.08

References

1. Nelson TD, Davis RD, Nelson WL..  (1994)  Synthesis and opioid receptor affinity of a series of aralkyl ethers of 6 alpha- and 6 beta-naltrexol.,  37  (25): [PMID:7996538] [10.1021/jm00051a003]

Source

Source(1):

• Scientific Literature