2-{[2-((2R)-2-{(1E,3S)-3-Hydroxy-4-[3-(2-naphthyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid

ID: ALA1957437

Chembl Id: CHEMBL1957437

PubChem CID: 57396660

Max Phase: Preclinical

Molecular Formula: C30H28N2O4S2

Molecular Weight: 544.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc(SCCN2C(=O)CC[C@@H]2/C=C/[C@@H](O)Cc2cccc(-c3ccc4ccccc4c3)c2)n1

Standard InChI:  InChI=1S/C30H28N2O4S2/c33-26(17-20-4-3-7-22(16-20)24-9-8-21-5-1-2-6-23(21)18-24)12-10-25-11-13-28(34)32(25)14-15-37-30-31-27(19-38-30)29(35)36/h1-10,12,16,18-19,25-26,33H,11,13-15,17H2,(H,35,36)/b12-10+/t25-,26+/m0/s1

Standard InChI Key:  PKTGJPBPSDSGSS-LRDZJWBWSA-N

Alternative Forms

1. Parent:

   

   ALA1957437

   2-[2-[(2R)-2-[(E,3S)-3-hydroxy-4-(3-naphthalen-2-ylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl]ethylsulfanyl]-1,3-thiazole-4-carboxylic 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: 544.70

Molecular Weight (Monoisotopic): 544.1490

AlogP: 5.90

#Rotatable Bonds: 10

Polar Surface Area: 90.73

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 5.81

CX LogD: 2.36

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: -0.35

References

1. Kambe T, Maruyama T, Nakai Y, Yoshida H, Oida H, Maruyama T, Abe N, Nishiura A, Nakai H, Toda M..  (2012)  Discovery of novel prostaglandin analogs as potent and selective EP2/EP4 dual agonists.,  20  (7): [PMID:22386979] [10.1016/j.bmc.2012.02.018]

2. Kambe T, Maruyama T, Nakai Y, Oida H, Maruyama T, Abe N, Nishiura A, Nakai H, Toda M..  (2012)  Synthesis and evaluation of γ-lactam analogs of PGE₂ as EP4 and EP2/EP4 agonists.,  20  (11): [PMID:22546206] [10.1016/j.bmc.2012.04.008]

Source

Source(1):

• Scientific Literature