(Z)-4-(3-((5-(4-Bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic Acid

ID: ALA565883

Chembl Id: CHEMBL565883

PubChem CID: 1723288

Max Phase: Preclinical

Molecular Formula: C28H18BrNO4

Molecular Weight: 512.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(N2C(=O)/C(=C\c3ccc(-c4ccc(Br)cc4)o3)C=C2c2ccccc2)cc1

Standard InChI:  InChI=1S/C28H18BrNO4/c29-22-10-6-19(7-11-22)26-15-14-24(34-26)16-21-17-25(18-4-2-1-3-5-18)30(27(21)31)23-12-8-20(9-13-23)28(32)33/h1-17H,(H,32,33)/b21-16-

Standard InChI Key:  PTNVXMRZJRXBHR-PGMHBOJBSA-N

Alternative Forms

1. Parent:

   

   ALA565883

   (Z)-4-(3-((5-(4-Bromophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic 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: 512.36

Molecular Weight (Monoisotopic): 511.0419

AlogP: 6.88

#Rotatable Bonds: 5

Polar Surface Area: 70.75

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.09

CX Basic pKa: ┄

CX LogP: 5.86

CX LogD: 2.76

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -0.71

References

1. Cosner CC, Markiewicz JT, Bourbon P, Mariani CJ, Wiest O, Rujoi M, Rosenbaum AI, Huang AY, Maxfield FR, Helquist P..  (2009)  Investigation of N-aryl-3-alkylidenepyrrolinones as potential Niemann-Pick type C disease therapeutics.,  52  (20): [PMID:19772346] [10.1021/jm900707n]

2. Waltenberger B, Wiechmann K, Bauer J, Markt P, Noha SM, Wolber G, Rollinger JM, Werz O, Schuster D, Stuppner H..  (2011)  Pharmacophore modeling and virtual screening for novel acidic inhibitors of microsomal prostaglandin E₂ synthase-1 (mPGES-1).,  54  (9): [PMID:21466167] [10.1021/jm101309g]

Source

Source(1):

• Scientific Literature