Ethyl 3-[(2E)-3-(4-cyanophenyl)prop-2-enoyl]-7-methoxyindolizine-1-carboxylate

ID: ALA3828274

PubChem CID: 127043146

Max Phase: Preclinical

Molecular Formula: C22H18N2O4

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(C(=O)/C=C/c2ccc(C#N)cc2)n2ccc(OC)cc12

Standard InChI:  InChI=1S/C22H18N2O4/c1-3-28-22(26)18-13-20(24-11-10-17(27-2)12-19(18)24)21(25)9-8-15-4-6-16(14-23)7-5-15/h4-13H,3H2,1-2H3/b9-8+

Standard InChI Key:  HPTUKFFFFVGZIK-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

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    5.5974   -4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0717   -6.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5412   -6.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5365   -5.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0623   -3.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5928   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -3.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808    3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560    0.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0068   -5.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1825   -5.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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 24 19  1  0
 22 25  1  0
 25 26  1  0
 27 28  3  0
  5 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3828274

   ---

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: 374.40

Molecular Weight (Monoisotopic): 374.1267

AlogP: 3.89

#Rotatable Bonds: 6

Polar Surface Area: 80.80

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -0.72

References

1. Moise IM, Ghinet A, Belei D, Dubois J, Farce A, Bîcu E..  (2016)  New indolizine-chalcones as potent inhibitors of human farnesyltransferase: Design, synthesis and biological evaluation.,  26  (15): [PMID:27282741] [10.1016/j.bmcl.2016.05.074]

Source

Source(1):

• Scientific Literature