3-Cyanopropyl 4-(5-methyl-3-phenylisoxazole-4-carboxamido)benzoate

ID: ALA4445681

PubChem CID: 155517910

Max Phase: Preclinical

Molecular Formula: C22H19N3O4

Molecular Weight: 389.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1onc(-c2ccccc2)c1C(=O)Nc1ccc(C(=O)OCCCC#N)cc1

Standard InChI:  InChI=1S/C22H19N3O4/c1-15-19(20(25-29-15)16-7-3-2-4-8-16)21(26)24-18-11-9-17(10-12-18)22(27)28-14-6-5-13-23/h2-4,7-12H,5-6,14H2,1H3,(H,24,26)

Standard InChI Key:  LDDWYPPFMBBGRI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    1.8078  -27.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017  -28.1461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806  -28.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718  -27.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905  -27.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020  -26.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202  -25.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4359  -24.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2296  -24.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056  -25.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5988  -26.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8252  -29.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890  -27.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2923  -28.4638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028  -27.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1094  -28.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5109  -29.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3273  -29.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7419  -28.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342  -27.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192  -27.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5591  -28.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9634  -29.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9720  -27.7837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7805  -29.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1848  -29.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0020  -29.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4063  -30.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8092  -31.3339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
  6 11  1  0
  3 12  1  0
  4 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4445681

   ---

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: 389.41

Molecular Weight (Monoisotopic): 389.1376

AlogP: 4.36

#Rotatable Bonds: 7

Polar Surface Area: 105.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.30

CX Basic pKa: ┄

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.39

References

1. 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