2-(4-methoxy-N-(4-(4-methoxyphenylsulfonamido)naphthalen-1-yl)phenylsulfonamido)acetic acid

ID: ALA3617852

Chembl Id: CHEMBL3617852

PubChem CID: 77461035

Max Phase: Preclinical

Molecular Formula: C26H24N2O8S2

Molecular Weight: 556.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)Nc2ccc(N(CC(=O)O)S(=O)(=O)c3ccc(OC)cc3)c3ccccc23)cc1

Standard InChI:  InChI=1S/C26H24N2O8S2/c1-35-18-7-11-20(12-8-18)37(31,32)27-24-15-16-25(23-6-4-3-5-22(23)24)28(17-26(29)30)38(33,34)21-13-9-19(36-2)10-14-21/h3-16,27H,17H2,1-2H3,(H,29,30)

Standard InChI Key:  NVQFDGYHTTZFJR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3617852

   N-[(4-methoxyphenyl)sulfonyl]-N-(4-{[(4-methoxyphenyl)sulfonyl]amino}naphthalen-1-yl)glycine

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: 556.62

Molecular Weight (Monoisotopic): 556.0974

AlogP: 3.94

#Rotatable Bonds: 10

Polar Surface Area: 139.31

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.88

CX Basic pKa:

CX LogP: 3.32

CX LogD: -0.24

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.30

Np Likeness Score: -1.18

References

1. Bertrand HC, Schaap M, Baird L, Georgakopoulos ND, Fowkes A, Thiollier C, Kachi H, Dinkova-Kostova AT, Wells G..  (2015)  Design, Synthesis, and Evaluation of Triazole Derivatives That Induce Nrf2 Dependent Gene Products and Inhibit the Keap1-Nrf2 Protein-Protein Interaction.,  58  (18): [PMID:26348784] [10.1021/acs.jmedchem.5b00602]

2. 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]

3. Georgakopoulos N, Talapatra S, Dikovskaya D, Dayalan Naidu S, Higgins M, Gatliff J, Ayhan A, Nikoloudaki R, Schaap M, Valko K, Javid F, Dinkova-Kostova AT, Kozielski F, Wells G..  (2022)  Phenyl Bis-Sulfonamide Keap1-Nrf2 Protein-Protein Interaction Inhibitors with an Alternative Binding Mode.,  65  (10.0): [PMID:35549469] [10.1021/acs.jmedchem.2c00457]

Source

Source(1):

• Scientific Literature