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

ID: ALA2037290

Chembl Id: CHEMBL2037290

PubChem CID: 58932678

Max Phase: Preclinical

Molecular Formula: C28H27N3O5S2

Molecular Weight: 549.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2oc(-c3cccc(C[C@H](O)/C=C/[C@H]4CCC(=O)N4CCSc4nc(C(=O)O)cs4)c3)nc12

Standard InChI:  InChI=1S/C28H27N3O5S2/c1-17-4-2-7-23-25(17)30-26(36-23)19-6-3-5-18(14-19)15-21(32)10-8-20-9-11-24(33)31(20)12-13-37-28-29-22(16-38-28)27(34)35/h2-8,10,14,16,20-21,32H,9,11-13,15H2,1H3,(H,34,35)/b10-8+/t20-,21+/m0/s1

Standard InChI Key:  LBKVVYLADFVUQO-BPFVEMAFSA-N

Alternative Forms

1. Parent:

   

   ALA2037290

   2-[2-[(2R)-2-[(E,3S)-3-hydroxy-4-[3-(4-methyl-1,3-benzoxazol-2-yl)phenyl]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: 549.67

Molecular Weight (Monoisotopic): 549.1392

AlogP: 5.20

#Rotatable Bonds: 10

Polar Surface Area: 116.76

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.17

CX Basic pKa: 0.44

CX LogP: 5.06

CX LogD: 1.60

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.20

Np Likeness Score: -0.61

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