ID: ALA2059381

Max Phase: Preclinical

Molecular Formula: C27H26FNO4

Molecular Weight: 447.51

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C27H26FNO4/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:  AWAQOPSDMCQZAA-PMDSDZCYSA-N

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

Properties

Molecular Weight: 447.51

Molecular Weight (Monoisotopic): 447.1846

AlogP: 3.36

#Rotatable Bonds: 3

Polar Surface Area: 70.00

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.11

CX Basic pKa: 8.92

CX LogP: 3.55

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.71

Np Likeness Score: 0.83

References

1. Miyata Y, Fujii H, Uenohara Y, Kobayashi S, Takeuchi T, Nagase H..  (2012)  Investigation of 7-benzylidenenaltrexone derivatives as resistance reverser for chloroquine-resistant Plasmodium chabaudi.,  22  (16): [PMID:22818080] [10.1016/j.bmcl.2012.06.085]

2. Kutsumura N, Nakajima R, Koyama Y, Miyata Y, Saitoh T, Yamamoto N, Iwata S, Fujii H, Nagase H..  (2015)  Investigation of 7-benzylidenenaltrexone derivatives as a novel structural antitrichomonal lead compound.,  25  (21): [PMID:26099536] [10.1016/j.bmcl.2015.06.002]

3. 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