(R)-3-benzyl-4-(cyclopropyl(4-(2,5-dichlorophenyl)thiazol-2-yl)amino)-4-oxobutanoic acid

ID: ALA4172928

Chembl Id: CHEMBL4172928

PubChem CID: 53302677

Max Phase: Preclinical

Molecular Formula: C23H20Cl2N2O3S

Molecular Weight: 475.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@@H](Cc1ccccc1)C(=O)N(c1nc(-c2cc(Cl)ccc2Cl)cs1)C1CC1

Standard InChI:  InChI=1S/C23H20Cl2N2O3S/c24-16-6-9-19(25)18(12-16)20-13-31-23(26-20)27(17-7-8-17)22(30)15(11-21(28)29)10-14-4-2-1-3-5-14/h1-6,9,12-13,15,17H,7-8,10-11H2,(H,28,29)/t15-/m1/s1

Standard InChI Key:  LCRQPJWEPVZEBE-OAHLLOKOSA-N

Alternative Forms

1. Parent:

   

   ALA4172928

   (3R)-3-benzyl-4-[cyclopropyl-[4-(2,5-dichlorophenyl)-1,3-thiazol-2-yl]amino]-4-oxobutanoic acid

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: 475.40

Molecular Weight (Monoisotopic): 474.0572

AlogP: 5.95

#Rotatable Bonds: 8

Polar Surface Area: 70.50

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.52

CX Basic pKa: ┄

CX LogP: 6.07

CX LogD: 3.28

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -1.14

References

1. Hansen AH, Sergeev E, Bolognini D, Sprenger RR, Ekberg JH, Ejsing CS, McKenzie CJ, Rexen Ulven E, Milligan G, Ulven T..  (2018)  Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties.,  61  (21): [PMID:30247908] [10.1021/acs.jmedchem.8b00855]

2. Hoveyda HR, Fraser GL, Zoute L, Dutheuil G, Schils D, Brantis C, Lapin A, Parcq J, Guitard S, Lenoir F, Bousmaqui ME, Rorive S, Hospied S, Blanc S, Bernard J, Ooms F, McNelis JC, Olefsky JM..  (2018)  N-Thiazolylamide-based free fatty-acid 2 receptor agonists: Discovery, lead optimization and demonstration of off-target effect in a diabetes model.,  26  (18): [PMID:30253886] [10.1016/j.bmc.2018.09.015]

3. Fells JI,Ai X,Weinglass A,Feng W,Lei Y,Finley M,Hoveyda HR,Fraser GL,Machacek M.  (2020)  Identification of free fatty acid receptor 2 agonists using virtual screening.,  30  (21.0): [PMID:32755680] [10.1016/j.bmcl.2020.127460]

Source

Source(1):

• Scientific Literature