(3-Methyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-pyridin-3-yl-methanone

ID: ALA353249

PubChem CID: 44383355

Max Phase: Preclinical

Molecular Formula: C24H23N3O3

Molecular Weight: 401.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)c2cccnc2)oc2cccc(OCCCNCc3cccnc3)c12

Standard InChI:  InChI=1S/C24H23N3O3/c1-17-22-20(29-13-5-12-26-15-18-6-3-10-25-14-18)8-2-9-21(22)30-24(17)23(28)19-7-4-11-27-16-19/h2-4,6-11,14,16,26H,5,12-13,15H2,1H3

Standard InChI Key:  ULKULPGKQKLXMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.1292   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917    1.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    1.4833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292    0.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4417   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
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  7  6  1  0
  8  4  2  0
  9  6  2  0
 10 16  2  0
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 20 15  1  0
 21 14  1  0
 22  7  2  0
 23  8  1  0
 24 30  2  0
 25 29  2  0
 26 19  1  0
 27 17  1  0
 28 12  2  0
 29 22  1  0
 30 28  1  0
  4  5  1  0
 23 21  2  0
 10 25  1  0
 11 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA353249

   [3-Methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-pyridin-3-ylmethanone

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: 401.47

Molecular Weight (Monoisotopic): 401.1739

AlogP: 4.32

#Rotatable Bonds: 9

Polar Surface Area: 77.25

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.70

CX LogP: 2.85

CX LogD: 1.54

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: -0.88

References

1. Kawasaki K, Masubuchi M, Morikami K, Sogabe S, Aoyama T, Ebiike H, Niizuma S, Hayase M, Fujii T, Sakata K, Shindoh H, Shiratori Y, Aoki Y, Ohtsuka T, Shimma N..  (2003)  Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 3.,  13  (1): [PMID:12467623] [10.1016/s0960-894x(02)00844-2]

Source

Source(1):

• Scientific Literature