5-isopropyl-5-(6-(naphthalen-2-yl)-2-oxo-1,2-dihydropyridin-3-yl)oxazolidine-2,4-dione

ID: ALA1770317

Chembl Id: CHEMBL1770317

Cas Number: 1227827-88-4

PubChem CID: 49850345

Max Phase: Preclinical

Molecular Formula: C21H18N2O4

Molecular Weight: 362.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C1(c2ccc(-c3ccc4ccccc4c3)[nH]c2=O)OC(=O)NC1=O

Standard InChI:  InChI=1S/C21H18N2O4/c1-12(2)21(19(25)23-20(26)27-21)16-9-10-17(22-18(16)24)15-8-7-13-5-3-4-6-14(13)11-15/h3-12H,1-2H3,(H,22,24)(H,23,25,26)

Standard InChI Key:  HXVAXOYPIPUCRY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1770317

   EP3 antagonist 3

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: 362.39

Molecular Weight (Monoisotopic): 362.1267

AlogP: 3.31

#Rotatable Bonds: 3

Polar Surface Area: 88.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.53

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 1.86

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.02

References

1. Morales-Ramos ÁI, Li YH, Hilfiker M, Mecom JS, Eidam P, Shi D, Tseng PS, Brooks C, Zhang D, Wang N, Jaworski JP, Morrow D, Fries H, Edwards R, Jin J..  (2011)  Structure-activity relationship studies of novel 3-oxazolidinedione-6-naphthyl-2-pyridinones as potent and orally bioavailable EP3 receptor antagonists.,  21  (10): [PMID:21514150] [10.1016/j.bmcl.2011.03.107]

2. Jin J, Morales-Ramos A, Eidam P, Mecom J, Li Y, Brooks C, Hilfiker M, Zhang D, Wang N, Shi D, Tseng PS, Wheless K, Budzik B, Evans K, Jaworski JP, Jugus J, Leon L, Wu C, Pullen M, Karamshi B, Rao P, Ward E, Laping N, Evans C, Leach C, Holt D, Su X, Morrow D, Fries H, Thorneloe K, Edwards R..  (2010)  Novel 3-Oxazolidinedione-6-aryl-pyridinones as Potent, Selective, and Orally Active EP3 Receptor Antagonists.,  1  (7): [PMID:24900213] [10.1021/ml100077x]

3. Zhang X,Zhu B,Guo L,Bakaj I,Rankin M,Ho G,Kauffman J,Lee SP,Norquay L,Macielag MJ.  (2021)  Discovery of a Novel Series of Pyridone-Based EP3 Antagonists for the Treatment of Type 2 Diabetes.,  12  (3): [PMID:33738072] [10.1021/acsmedchemlett.0c00667]

Source

Source(1):

• Scientific Literature