ID: ALA3310358

Max Phase: Preclinical

Molecular Formula: C24H18N4O4S

Molecular Weight: 458.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)/C(Cc1ccccc1[N+](=O)[O-])=N\Nc1nc(-c2ccc(-c3ccccc3)cc2)cs1

Standard InChI:  InChI=1S/C24H18N4O4S/c29-23(30)20(14-19-8-4-5-9-22(19)28(31)32)26-27-24-25-21(15-33-24)18-12-10-17(11-13-18)16-6-2-1-3-7-16/h1-13,15H,14H2,(H,25,27)(H,29,30)/b26-20-

Standard InChI Key:  JKEOZOHBIPDTTJ-QOMWVZHYSA-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: 458.50

Molecular Weight (Monoisotopic): 458.1049

AlogP: 5.48

#Rotatable Bonds: 8

Polar Surface Area: 117.72

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.16

CX Basic pKa: 1.77

CX LogP: 6.73

CX LogD: 3.57

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -1.27

References

1. Takrouri K, Chen T, Papadopoulos E, Sahoo R, Kabha E, Chen H, Cantel S, Wagner G, Halperin JA, Aktas BH, Chorev M..  (2014)  Structure-activity relationship study of 4EGI-1, small molecule eIF4E/eIF4G protein-protein interaction inhibitors.,  77  [PMID:24675136] [10.1016/j.ejmech.2014.03.034]

2. Fischer PD, Papadopoulos E, Dempersmier JM, Wang ZF, Nowak RP, Donovan KA, Kalabathula J, Gorgulla C, Junghanns PPM, Kabha E, Dimitrakakis N, Petrov OI, Mitsiades C, Ducho C, Gelev V, Fischer ES, Wagner G, Arthanari H..  (2021)  A biphenyl inhibitor of eIF4E targeting an internal binding site enables the design of cell-permeable PROTAC-degraders.,  219  [PMID:33892272] [10.1016/j.ejmech.2021.113435]

Source

Source(1):

• Scientific Literature