7(E)-(3-Cyanobenzylidene)naltrexone

ID: ALA4096636

PubChem CID: 137654581

Max Phase: Preclinical

Molecular Formula: C28H26N2O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cccc(/C=C2\C[C@@]3(O)[C@H]4Cc5ccc(O)c6c5[C@@]3(CCN4CC3CC3)[C@@H](O6)C2=O)c1

Standard InChI:  InChI=1S/C28H26N2O4/c29-14-18-3-1-2-17(10-18)11-20-13-28(33)22-12-19-6-7-21(31)25-23(19)27(28,26(34-25)24(20)32)8-9-30(22)15-16-4-5-16/h1-3,6-7,10-11,16,22,26,31,33H,4-5,8-9,12-13,15H2/b20-11+/t22-,26+,27+,28-/m1/s1

Standard InChI Key:  OJLDPMNDSAPRSY-RLEPZMFISA-N

Molfile:  

     RDKit          2D

 36 42  0  0  0  0  0  0  0  0999 V2000
    5.4025   -4.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8111   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5854   -4.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988   -5.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -5.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9568   -5.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778   -3.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4025   -2.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5854   -3.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6283   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6159   -5.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8111   -1.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3719   -5.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816   -3.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6283   -1.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -2.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3341   -1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3719   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0369   -4.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2197   -3.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245   -6.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -4.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510   -6.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918   -2.9097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988   -6.3394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8541   -4.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2673   -4.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0836   -4.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4967   -3.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0927   -2.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2713   -2.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8619   -3.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3094   -3.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1266   -3.3490    0.0000 N   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
  1 11  1  1
 12  2  1  0
 13  4  1  0
 14  8  1  0
 15  5  1  0
 16 11  1  0
 17 14  1  0
 18 17  1  0
 19 17  1  0
 20  9  2  0
 21 13  1  0
  2 22  1  1
 23 13  2  0
 24 20  1  0
 25 15  1  0
  7 26  1  6
  4 27  1  1
  5  6  1  0
  8  7  1  0
 21 12  1  0
 10  7  1  0
 24 15  2  0
 18 19  1  0
 21 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 35 36  3  0
 31 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096636

   ---

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: 454.53

Molecular Weight (Monoisotopic): 454.1893

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 93.79

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 8.90

CX LogP: 3.27

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.69

Np Likeness Score: 0.67

References

1. Kutsumura N, Koyama Y, Nagumo Y, Nakajima R, Miyata Y, Yamamoto N, Saitoh T, Yoshida N, Iwata S, Nagase H..  (2017)  Antitrichomonal activity of δ opioid receptor antagonists, 7-benzylidenenaltrexone derivatives.,  25  (16): [PMID:28662966] [10.1016/j.bmc.2017.06.026]

Source

Source(1):

• Scientific Literature