Ethyl (Z)-5-((1H-pyrrolo[3,2-b]pyridin-2-yl)methylene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate

ID: ALA5195225

PubChem CID: 168289936

Max Phase: Preclinical

Molecular Formula: C21H17N3O3S

Molecular Weight: 391.45

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(Nc2ccccc2)S/C(=C\c2cc3ncccc3[nH]2)C1=O

Standard InChI:  InChI=1S/C21H17N3O3S/c1-2-27-21(26)18-19(25)17(28-20(18)24-13-7-4-3-5-8-13)12-14-11-16-15(23-14)9-6-10-22-16/h3-12,23-24H,2H2,1H3/b17-12-

Standard InChI Key:  BXSRZRACIZHJET-ATVHPVEESA-N

Molfile:  

 
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    0.5640    2.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4564   -1.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2528   -1.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -0.9097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5195225

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 391.45

Molecular Weight (Monoisotopic): 391.0991

AlogP: 4.11

#Rotatable Bonds: 5

Polar Surface Area: 84.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.04

CX Basic pKa: 4.43

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: -1.13

References

1. Hwang J, Qiu X, Borgelt L, Haacke N, Kanis L, Petroulia S, Gasper R, Schiller D, Lampe P, Sievers S, Imig J, Wu P..  (2022)  Synthesis and evaluation of RNase L-binding 2-aminothiophenes as anticancer agents.,  58  [PMID:35152173] [10.1016/j.bmc.2022.116653]

2. Duvauchelle V, Meffre P, Benfodda Z..  (2022)  Recent contribution of medicinally active 2-aminothiophenes: A privileged scaffold for drug discovery.,  238  [PMID:35696863] [10.1016/j.ejmech.2022.114502]

Source

Source(1):

• Scientific Literature