N-(2-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxamido)ethyl)-5-methoxybenzofuran-2-carboxamide

ID: ALA4475642

PubChem CID: 155538120

Max Phase: Preclinical

Molecular Formula: C22H28N2O4

Molecular Weight: 384.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2oc(C(=O)NCCNC(=O)C3C(C=C(C)C)C3(C)C)cc2c1

Standard InChI:  InChI=1S/C22H28N2O4/c1-13(2)10-16-19(22(16,3)4)21(26)24-9-8-23-20(25)18-12-14-11-15(27-5)6-7-17(14)28-18/h6-7,10-12,16,19H,8-9H2,1-5H3,(H,23,25)(H,24,26)

Standard InChI Key:  FTXSDQMEJYTDED-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.3552   -1.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541   -2.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603   -1.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7690   -1.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7692   -2.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5522   -2.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359   -2.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5518   -1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6474   -1.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8531   -2.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2619   -2.8854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614   -1.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791   -2.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4880   -3.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3052   -3.5924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7140   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5312   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3056   -5.0078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2395   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2392   -3.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6499   -5.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4671   -5.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8775   -6.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0209   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9413   -3.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 21 19  1  0
 22 21  1  0
 19 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 22 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475642

   ---

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: 384.48

Molecular Weight (Monoisotopic): 384.2049

AlogP: 3.53

#Rotatable Bonds: 7

Polar Surface Area: 80.57

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -0.12

References

1. Ragle LE, Palanisamy DJ, Joe MJ, Stein RS, Norman DD, Tigyi G, Baker DL, Parrill AL..  (2016)  Discovery and synthetic optimization of a novel scaffold for hydrophobic tunnel-targeted autotaxin inhibition.,  24  (19): [PMID:27544588] [10.1016/j.bmc.2016.08.004]

Source

Source(1):

• Scientific Literature