N-(4-chlorophenyl)-5-methyl-N-(4-methyl-4,5-dihydrothiazol-2-yl)-3-phenylisoxazole-4-carboxamide

ID: ALA4102758

Cas Number: 878090-53-0

PubChem CID: 16283482

Max Phase: Preclinical

Molecular Formula: C21H18ClN3O2S

Molecular Weight: 411.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1onc(-c2ccccc2)c1C(=O)N(C1=NC(C)CS1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H18ClN3O2S/c1-13-12-28-21(23-13)25(17-10-8-16(22)9-11-17)20(26)18-14(2)27-24-19(18)15-6-4-3-5-7-15/h3-11,13H,12H2,1-2H3

Standard InChI Key:  GKELNWVZTJUVJN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.7963   -9.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0507   -8.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3877   -7.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7290   -8.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8282   -7.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3865   -6.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0935   -6.5282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6781   -6.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0923   -5.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7985   -5.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7976   -4.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0887   -4.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3793   -4.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837   -5.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9517   -7.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847   -7.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082   -6.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4002   -7.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3502   -8.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0864   -3.2617    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8019   -6.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8904   -7.7452    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6900   -7.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0975   -7.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5497   -6.5991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9101   -7.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  8 23  1  0
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 27 23  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4102758

   N-(4-Chlorophenyl)-5-methyl-N-(4-methyl-4,5-dihydrothiazol-2-yl)-3-phenylisoxazole-4-carboxamide

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: 411.91

Molecular Weight (Monoisotopic): 411.0808

AlogP: 5.44

#Rotatable Bonds: 3

Polar Surface Area: 58.70

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.12

CX LogP: 5.49

CX LogD: 5.49

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.25

References

1. Välimäki MJ, Tölli MA, Kinnunen SM, Aro J, Serpi R, Pohjolainen L, Talman V, Poso A, Ruskoaho HJ..  (2017)  Discovery of Small Molecules Targeting the Synergy of Cardiac Transcription Factors GATA4 and NKX2-5.,  60  (18): [PMID:28858485] [10.1021/acs.jmedchem.7b00816]

2. Jumppanen M, Kinnunen SM, Välimäki MJ, Talman V, Auno S, Bruun T, Boije Af Gennäs G, Xhaard H, Aumüller IB, Ruskoaho H, Yli-Kauhaluoma J..  (2019)  Synthesis, Identification, and Structure-Activity Relationship Analysis of GATA4 and NKX2-5 Protein-Protein Interaction Modulators.,  62  (17): [PMID:31431011] [10.1021/acs.jmedchem.9b01086]

Source

Source(1):

• Scientific Literature