5-(8-Hydroxy-6,11-dimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-ylmethyl)-3-methylene-dihydro-furan-2-one

ID: ALA2367763

PubChem CID: 73346788

Max Phase: Preclinical

Molecular Formula: C20H25NO3

Molecular Weight: 327.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C[C@@H](CN2CC[C@@]3(C)c4cc(O)ccc4C[C@H]2[C@H]3C)OC1=O

Standard InChI:  InChI=1S/C20H25NO3/c1-12-8-16(24-19(12)23)11-21-7-6-20(3)13(2)18(21)9-14-4-5-15(22)10-17(14)20/h4-5,10,13,16,18,22H,1,6-9,11H2,2-3H3/t13-,16+,18+,20-/m1/s1

Standard InChI Key:  FXAWKCNYVHSHJZ-BUJNREJVSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    1.8062   -6.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120   -6.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614   -5.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051   -5.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993   -5.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499   -6.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581   -4.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3893   -3.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8395   -3.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009   -4.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -3.8479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8240   -3.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -4.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7936   -4.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844   -3.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -3.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -4.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -4.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7503   -3.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -2.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4951   -2.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672   -4.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071   -2.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683   -7.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -4.5769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  5  6  1  0
  4  7  1  0
  4  5  2  0
 10  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  1
  7 13  1  0
 11 14  1  0
 14 13  1  0
 11 15  1  0
 16 15  1  1
 16 17  1  0
 16 20  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  2  0
  8 23  1  1
  2 24  1  0
  9 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2367763

   (5S)-5-[[(1R,9S,13S)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-10-yl]methyl]-3-methylideneoxolan-2-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: 327.42

Molecular Weight (Monoisotopic): 327.1834

AlogP: 2.79

#Rotatable Bonds: 2

Polar Surface Area: 49.77

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.36

CX Basic pKa: 9.36

CX LogP: 3.34

CX LogD: 1.61

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 2.09

References

1. Klein P, Nelson WL..  (1991)  Electrophilic gamma-lactone kappa-opioid receptor probes. Analogues of 2'-hydroxy-2-tetrahydrofurfuryl-5,9-dimethyl-6,7-benzomorphan diastereomers.,  34  (8): [PMID:1652019] [10.1021/jm00112a019]

Source

Source(1):

• Scientific Literature