ID: ALA3632711

Max Phase: Preclinical

Molecular Formula: C28H28N4O8S2

Molecular Weight: 612.69

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(S(=O)(=O)N(CC(N)=O)c2ccc(N(CC(N)=O)S(=O)(=O)c3ccc(OC)cc3)c3ccccc23)cc1

Standard InChI:  InChI=1S/C28H28N4O8S2/c1-39-19-7-11-21(12-8-19)41(35,36)31(17-27(29)33)25-15-16-26(24-6-4-3-5-23(24)25)32(18-28(30)34)42(37,38)22-13-9-20(40-2)10-14-22/h3-16H,17-18H2,1-2H3,(H2,29,33)(H2,30,34)

Standard InChI Key:  ZUIXHSIMKQZYPV-UHFFFAOYSA-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: 612.69

Molecular Weight (Monoisotopic): 612.1349

AlogP: 2.22

#Rotatable Bonds: 12

Polar Surface Area: 179.40

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.86

CX Basic pKa:

CX LogP: 1.41

CX LogD: 1.41

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.24

Np Likeness Score: -0.79

References

1. Jain AD, Potteti H, Richardson BG, Kingsley L, Luciano JP, Ryuzoji AF, Lee H, Krunic A, Mesecar AD, Reddy SP, Moore TW..  (2015)  Probing the structural requirements of non-electrophilic naphthalene-based Nrf2 activators.,  103  [PMID:26363505] [10.1016/j.ejmech.2015.08.049]

2. Richardson BG, Jain AD, Potteti HR, Lazzara PR, David BP, Tamatam CR, Choma E, Skowron K, Dye K, Siddiqui Z, Wang YT, Krunic A, Reddy SP, Moore TW..  (2018)  Replacement of a Naphthalene Scaffold in Kelch-like ECH-Associated Protein 1 (KEAP1)/Nuclear Factor (Erythroid-derived 2)-like 2 (NRF2) Inhibitors.,  61  (17): [PMID:30122040] [10.1021/acs.jmedchem.8b01133]

3. Tran KT, Pallesen JS, Solbak SMØ, Narayanan D, Baig A, Zang J, Aguayo-Orozco A, Carmona RMC, Garcia AD, Bach A..  (2019)  A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity.,  62  (17): [PMID:31411465] [10.1021/acs.jmedchem.9b00723]

4. Mou Y, Wen S, Li YX, Gao XX, Zhang X, Jiang ZY..  (2020)  Recent progress in Keap1-Nrf2 protein-protein interaction inhibitors.,  202  [PMID:32668381] [10.1016/j.ejmech.2020.112532]

Source

Source(1):

• Scientific Literature