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

ID: ALA2036325

Chembl Id: CHEMBL2036325

PubChem CID: 10348321

Max Phase: Preclinical

Molecular Formula: C27H24ClN3O4S3

Molecular Weight: 586.16

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(-c3nc4cc(Cl)ccc4s3)c2)n1

Standard InChI:  InChI=1S/C27H24ClN3O4S3/c28-18-4-8-23-21(14-18)29-25(38-23)17-3-1-2-16(12-17)13-20(32)7-5-19-6-9-24(33)31(19)10-11-36-27-30-22(15-37-27)26(34)35/h1-5,7-8,12,14-15,19-20,32H,6,9-11,13H2,(H,34,35)/b7-5+/t19-,20+/m0/s1

Standard InChI Key:  COBKGDMIGLRUQR-CNIPWFDFSA-N

Alternative Forms

1. Parent:

   

   ALA2036325

   2-[2-[(2R)-2-[(E,3S)-4-[3-(5-chloro-1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-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: 586.16

Molecular Weight (Monoisotopic): 585.0617

AlogP: 6.01

#Rotatable Bonds: 10

Polar Surface Area: 103.62

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.19

CX Basic pKa: 1.80

CX LogP: 5.70

CX LogD: 2.49

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.17

Np Likeness Score: -1.09

References

1. 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