CmpdA

ID: ALA5074567

PubChem CID: 71664582

Max Phase: Preclinical

Molecular Formula: C20H14ClN3O2S2

Molecular Weight: 427.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc2c(-c3ccc(C(=O)NCc4ccnc(Cl)c4)s3)cccc2s1

Standard InChI:  InChI=1S/C20H14ClN3O2S2/c21-18-8-11(6-7-23-18)10-24-20(26)16-5-4-15(27-16)12-2-1-3-14-13(12)9-17(28-14)19(22)25/h1-9H,10H2,(H2,22,25)(H,24,26)

Standard InChI Key:  SKAFXNGFXPGQIG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -5.7221   -1.8037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231   -2.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231   -4.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1240   -1.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.3119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918   -2.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3037   -4.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0046   -4.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899   -3.9684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478   -6.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613   -7.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -7.0740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207   -8.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -9.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -8.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -8.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902  -10.3961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767  -11.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335  -12.7695    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064  -10.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 12  4  1  0
 11  6  1  0
 17 13  1  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5074567

   4-(5-{[(2-Chloropyridin-4-Yl)methyl]carbamoyl}thiophen-2-Yl)-1-Benzothiophene-2-Carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 427.94

Molecular Weight (Monoisotopic): 427.0216

AlogP: 4.71

#Rotatable Bonds: 5

Polar Surface Area: 85.08

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.78

CX Basic pKa: 1.05

CX LogP: 3.79

CX LogD: 3.79

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -1.64

References

1.  (2022)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomis Library 2 (Incucyte),  [10.6019/CHEMBL5058564]

2. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

3. Segretti ND, Takarada JE, Ferreira MA, da Silva Santiago A, Teodoro BVM, Damião MCFCB, Godoi PH, Cunha MR, Fala AM, Ramos PZ, Ishikawa EE, Mascarello A, Serafim RAM, Azevedo H, Guimarães CRW, Couñago RM..  (2022)  Discovery of novel benzothiophene derivatives as potent and narrow spectrum inhibitors of DYRK1A and DYRK1B.,  68  [PMID:35504513] [10.1016/j.bmcl.2022.128764]

4. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

Source

Source(2):

• Scientific Literature
• EUbOPEN Chemogenomic Library