2-(4-Chloro-phenylamino)-4-oxo-4,5-dihydro-furan-3-carboxylic acid ethyl ester

ID: ALA56654

Chembl Id: CHEMBL56654

Cas Number: 58337-17-0

PubChem CID: 2822532

Max Phase: Preclinical

Molecular Formula: C13H12ClNO4

Molecular Weight: 281.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(Nc2ccc(Cl)cc2)OCC1=O

Standard InChI:  InChI=1S/C13H12ClNO4/c1-2-18-13(17)11-10(16)7-19-12(11)15-9-5-3-8(14)4-6-9/h3-6,15H,2,7H2,1H3

Standard InChI Key:  KRJWNHKSBHBACC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA56654

   Ethyl 2-[(4-chlorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate

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: 281.70

Molecular Weight (Monoisotopic): 281.0455

AlogP: 2.13

#Rotatable Bonds: 4

Polar Surface Area: 64.63

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 5.48

CX Basic pKa:

CX LogP: 2.73

CX LogD: 1.43

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.68

Np Likeness Score: -0.62

References

1. Mack RA, Zazulak WI, Radov LA, Baer JE, Stewart JD, Elzer PH, Kinsolving CR, Georgiev VS..  (1988)  Drug-induced modifications of the immune response. 12. 4,5-Dihydro-4-oxo-2-(substituted amino)-3-furancarboxylic acids and derivatives as novel antiallergic agents.,  31  (10): [PMID:3172125] [10.1021/jm00118a008]

2. PubChem BioAssay data set, 

3. Lien JC, Lin CS, Lai HC, Tsai YC, Lin YF, Huang AC, Huang SH, Lin CW..  (2019)  Antiviral efficacy of bromo-anilino substituents of 4,5-dihydrofuran-3-carboxylate compound CW-33 against Japanese encephalitis virus.,  29  (23): [PMID:31648857] [10.1016/j.bmcl.2019.126742]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays