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

ID: ALA170807

PubChem CID: 500952

Max Phase: Preclinical

Molecular Formula: C25H25N3O3

Molecular Weight: 415.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)c2oc3cccc(OCCCNCc4cccnc4)c3c2C)nc1

Standard InChI:  InChI=1S/C25H25N3O3/c1-17-9-10-20(28-14-17)24(29)25-18(2)23-21(7-3-8-22(23)31-25)30-13-5-12-27-16-19-6-4-11-26-15-19/h3-4,6-11,14-15,27H,5,12-13,16H2,1-2H3

Standard InChI Key:  DRSIHXSBXYQZDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.0417   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -2.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -0.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125    1.4583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917    1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625    1.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5125   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500    0.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750    1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375    0.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042    0.2208    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
  5  1  1  0
  6  3  1  0
  7  8  2  0
  8  5  1  0
  9  4  2  0
 10  5  2  0
 11 21  2  0
 12  8  1  0
 13  7  1  0
 14 23  1  0
 15  2  1  0
 16  6  2  0
 17 27  1  0
 18 19  1  0
 19 12  2  0
 20  9  1  0
 21 14  1  0
 22 28  1  0
 23 17  1  0
 24 16  1  0
 25  9  1  0
 26 31  2  0
 27 22  1  0
 28 20  1  0
 29 14  2  0
 30 18  1  0
 31 29  1  0
  4  6  1  0
 25 24  2  0
 13 18  2  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA170807

   (3-Methyl-4-(3-(pyridin-3-ylmethylamino)propoxy)benzofuran-2-yl)(5-methylpyridin-2-yl)methanone

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: 415.49

Molecular Weight (Monoisotopic): 415.1896

AlogP: 4.63

#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: 3.75

CX LogD: 2.44

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: -1.04

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]

2. Sheng C, Zhu J, Zhang W, Zhang M, Ji H, Song Y, Xu H, Yao J, Miao Z, Zhou Y, Zhu J, Lü J..  (2007)  3D-QSAR and molecular docking studies on benzothiazole derivatives as Candida albicans N-myristoyltransferase inhibitors.,  42  (4): [PMID:17349719] [10.1016/j.ejmech.2006.11.001]

Source

Source(1):

• Scientific Literature