7(E)-(4-Iodobenzylidene)naltrexone

ID: ALA4092119

PubChem CID: 137652971

Max Phase: Preclinical

Molecular Formula: C27H26INO4

Molecular Weight: 555.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(I)cc2)C[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C27H26INO4/c28-19-6-3-15(4-7-19)11-18-13-27(32)21-12-17-5-8-20(30)24-22(17)26(27,25(33-24)23(18)31)9-10-29(21)14-16-1-2-16/h3-8,11,16,21,25,30,32H,1-2,9-10,12-14H2/b18-11+/t21-,25+,26+,27-/m1/s1

Standard InChI Key:  JJAWOYXUCMECPB-PMDSDZCYSA-N

Molfile:  

     RDKit          2D

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   25.2297  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.3696  -13.7230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5104  -10.4832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.2174  -13.9129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7 26  1  6
  4 27  1  1
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 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092119

   ---

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: 555.41

Molecular Weight (Monoisotopic): 555.0907

AlogP: 3.82

#Rotatable Bonds: 3

Polar Surface Area: 70.00

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.11

CX Basic pKa: 8.91

CX LogP: 4.34

CX LogD: 3.09

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: 0.83

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