ID: ALA2059382

Max Phase: Preclinical

Molecular Formula: C28H29NO5

Molecular Weight: 459.54

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(/C=C2\C[C@@]3(O)[C@H]4Cc5ccc(O)c6c5[C@@]3(CCN4CC3CC3)[C@@H](O6)C2=O)cc1

Standard InChI:  InChI=1S/C28H29NO5/c1-33-20-7-4-16(5-8-20)12-19-14-28(32)22-13-18-6-9-21(30)25-23(18)27(28,26(34-25)24(19)31)10-11-29(22)15-17-2-3-17/h4-9,12,17,22,26,30,32H,2-3,10-11,13-15H2,1H3/b19-12+/t22-,26+,27+,28-/m1/s1

Standard InChI Key:  VZAMOSHZVIQLPK-BBWRIMMGSA-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: 459.54

Molecular Weight (Monoisotopic): 459.2046

AlogP: 3.23

#Rotatable Bonds: 4

Polar Surface Area: 79.23

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.11

CX Basic pKa: 8.92

CX LogP: 3.25

CX LogD: 1.99

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.68

Np Likeness Score: 1.03

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