Ethyl-5-((1H-pyrrol-2-yl)methylene)-2-((3-nitrophenyl)amino)-4-oxo-4,5-dihydrothiophene-3-carboxylate

ID: ALA5184382

PubChem CID: 168282991

Max Phase: Preclinical

Molecular Formula: C18H15N3O5S

Molecular Weight: 385.40

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(Nc2cccc([N+](=O)[O-])c2)S/C(=C\c2ccc[nH]2)C1=O

Standard InChI:  InChI=1S/C18H15N3O5S/c1-2-26-18(23)15-16(22)14(10-11-6-4-8-19-11)27-17(15)20-12-5-3-7-13(9-12)21(24)25/h3-10,19-20H,2H2,1H3/b14-10-

Standard InChI Key:  QHYRGIPMYIQMSV-UVTDQMKNSA-N

Molfile:  

 
     RDKit          2D

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   -1.4770    0.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220    0.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970    0.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421    0.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.1629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8680   -0.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6647   -1.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8769   -1.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934   -2.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5002   -2.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2823   -1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153    1.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970    2.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153    2.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    1.5495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    1.5495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -0.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871   -0.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -2.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -2.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2569   -1.2551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6736   -2.1815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8871   -2.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569   -1.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
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  6  7  1  0
  8  7  2  0
  9  8  1  0
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  7 12  1  0
  4 13  1  0
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 15 16  1  0
 13 17  2  0
  3 18  2  0
  2 19  2  0
 19 20  1  0
 21 20  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
 25  9  1  0
 25 26  1  0
 25 27  2  0
M  CHG  2  25   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5184382

   ---

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: 385.40

Molecular Weight (Monoisotopic): 385.0732

AlogP: 3.47

#Rotatable Bonds: 6

Polar Surface Area: 114.33

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.67

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: -1.40

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