7(E)-[(2-Furyl)methylene]naltrexone

ID: ALA4092231

PubChem CID: 137654182

Max Phase: Preclinical

Molecular Formula: C25H25NO5

Molecular Weight: 419.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccco2)C[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C25H25NO5/c27-18-6-5-15-11-19-25(29)12-16(10-17-2-1-9-30-17)21(28)23-24(25,20(15)22(18)31-23)7-8-26(19)13-14-3-4-14/h1-2,5-6,9-10,14,19,23,27,29H,3-4,7-8,11-13H2/b16-10+/t19-,23+,24+,25-/m1/s1

Standard InChI Key:  QEDBJCANPFBHAG-JCJKLZQWSA-N

Molfile:  

     RDKit          2D

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   25.0812  -11.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8554  -12.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.4592  -11.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.2293  -12.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2210  -13.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3618  -10.3593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.0688  -13.7891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1241  -12.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5373  -11.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3498  -11.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   27.2091  -10.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 22  1  1
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 24 20  1  0
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  7 26  1  6
  4 27  1  1
  5  6  1  0
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 24 15  2  0
 18 19  1  0
 21 28  2  0
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 29 30  1  0
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 31 32  2  0
 32 33  1  0
 33 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092231

   ---

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: 419.48

Molecular Weight (Monoisotopic): 419.1733

AlogP: 2.81

#Rotatable Bonds: 3

Polar Surface Area: 83.14

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.10

CX Basic pKa: 8.84

CX LogP: 2.50

CX LogD: 1.30

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.74

Np Likeness Score: 0.90

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