(E)-4-oxo-4-(4-(phenylamino)phenylamino)but-2-enoic acid

ID: ALA395102

Chembl Id: CHEMBL395102

Cas Number: 1426263-36-6

PubChem CID: 675816

Max Phase: Preclinical

Molecular Formula: C16H14N2O3

Molecular Weight: 282.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C=C/C(=O)Nc1ccc(Nc2ccccc2)cc1

Standard InChI:  InChI=1S/C16H14N2O3/c19-15(10-11-16(20)21)18-14-8-6-13(7-9-14)17-12-4-2-1-3-5-12/h1-11,17H,(H,18,19)(H,20,21)/b11-10+

Standard InChI Key:  QBYWTLIASGXCDV-ZHACJKMWSA-N

Alternative Forms

1. Parent:

   

   ALA395102

   (E)-4-(4-anilinoanilino)-4-oxobut-2-enoic 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: 282.30

Molecular Weight (Monoisotopic): 282.1004

AlogP: 3.01

#Rotatable Bonds: 5

Polar Surface Area: 78.43

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.28

CX Basic pKa: 0.71

CX LogP: 2.83

CX LogD: -0.60

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.74

Np Likeness Score: -0.64

References

1. Furci LM, Lopes P, Eakanunkul S, Zhong S, MacKerell AD, Wilks A..  (2007)  Inhibition of the bacterial heme oxygenases from Pseudomonas aeruginosa and Neisseria meningitidis: novel antimicrobial targets.,  50  (16): [PMID:17629261] [10.1021/jm0700969]

2. Hom K, Heinzl GA, Eakanunkul S, Lopes PE, Xue F, MacKerell AD, Wilks A..  (2013)  Small molecule antivirulents targeting the iron-regulated heme oxygenase (HemO) of P. aeruginosa.,  56  (5): [PMID:23379514] [10.1021/jm301819k]

3.  (2013)  Heme oxygenase inhibitors, screening methods for heme oxygenase inhibitors and methods of use of heme oxygenase inhibitors for antimicrobial therapy, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data