(1r,3r)-3-(5-(4-(N-tert-butylsulfamoyl)naphthalen-1-yl)-4-(cyclohexylmethyl)thiazole-2-carboxamido)cyclobutanecarboxylic acid

ID: ALA4128926

Chembl Id: CHEMBL4128926

PubChem CID: 72548703

Max Phase: Preclinical

Molecular Formula: C30H37N3O5S2

Molecular Weight: 583.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NS(=O)(=O)c1ccc(-c2sc(C(=O)N[C@H]3C[C@H](C(=O)O)C3)nc2CC2CCCCC2)c2ccccc12

Standard InChI:  InChI=1S/C30H37N3O5S2/c1-30(2,3)33-40(37,38)25-14-13-23(21-11-7-8-12-22(21)25)26-24(15-18-9-5-4-6-10-18)32-28(39-26)27(34)31-20-16-19(17-20)29(35)36/h7-8,11-14,18-20,33H,4-6,9-10,15-17H2,1-3H3,(H,31,34)(H,35,36)/t19-,20-

Standard InChI Key:  KYIGOCCCBXRHNJ-MXVIHJGJSA-N

Alternative Forms

1. Parent:

   

   ALA4128926

   US10301272, Example 7/9

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: 583.78

Molecular Weight (Monoisotopic): 583.2175

AlogP: 5.76

#Rotatable Bonds: 8

Polar Surface Area: 125.46

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.14

CX Basic pKa: ┄

CX LogP: 5.17

CX LogD: 2.09

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.31

Np Likeness Score: -0.76

References

1. Gege C, Cummings MD, Albers M, Kinzel O, Kleymann G, Schlüter T, Steeneck C, Nelen MI, Milligan C, Spurlino J, Xue X, Leonard K, Edwards JP, Fourie A, Goldberg SD, Hoffmann T..  (2018)  Identification and biological evaluation of thiazole-based inverse agonists of RORγt.,  28  (9): [PMID:29631962] [10.1016/j.bmcl.2018.03.093]

2. Steeneck C, Gege C, Kinzel O, Albers M, Kleymann G, Schlüter T, Schulz A, Xue X, Cummings MD, Fourie AM, Leonard KA, Scott B, Edwards JP, Hoffmann T, Goldberg SD..  (2020)  Discovery and optimization of new oxadiazole substituted thiazole RORγt inverse agonists through a bioisosteric amide replacement approach.,  30  (12): [PMID:32334912] [10.1016/j.bmcl.2020.127174]

Source

Source(1):

• Scientific Literature