4-(3-tert-Butylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

ID: ALA53935

PubChem CID: 489107

Max Phase: Preclinical

Molecular Formula: C19H27NO4

Molecular Weight: 333.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1oc2cccc(OCCCNC(C)(C)C)c2c1C

Standard InChI:  InChI=1S/C19H27NO4/c1-6-22-18(21)17-13(2)16-14(9-7-10-15(16)24-17)23-12-8-11-20-19(3,4)5/h7,9-10,20H,6,8,11-12H2,1-5H3

Standard InChI Key:  RIYRHNUSSZPXRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.9125   -9.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -9.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292  -10.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -9.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417  -10.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375   -9.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -9.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542  -10.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -8.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -6.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -9.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167  -10.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -8.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042  -10.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -9.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -7.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -6.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -5.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -9.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -8.4167    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  3  1  0
  6  1  1  0
  7  4  2  0
  8  6  2  0
  9 11  1  0
 10  2  1  0
 11 18  1  0
 12  6  1  0
 13  5  2  0
 14  7  1  0
 15 19  1  0
 16 13  1  0
 17  7  1  0
 18 15  1  0
 19 14  1  0
 20  9  1  0
 21  9  1  0
 22  9  1  0
 23 12  1  0
 24 23  1  0
  4  5  1  0
 17 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA53935

   4-(3-tert-Butylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

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: 333.43

Molecular Weight (Monoisotopic): 333.1940

AlogP: 4.07

#Rotatable Bonds: 7

Polar Surface Area: 60.70

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.36

CX LogP: 3.52

CX LogD: 0.74

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.71

References

1. Masubuchi M, Kawasaki K, Ebiike H, Ikeda Y, Tsujii S, Sogabe S, Fujii T, Sakata K, Shiratori Y, Aoki Y, Ohtsuka T, Shimma N..  (2001)  Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1.,  11  (14): [PMID:11459642] [10.1016/s0960-894x(01)00319-5]

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]

3. Deokar HS, Puranik P, Kulkarni VM.  (2009)  QSAR analysis of N-myristoyltransferase inhibitors: antifungal activity of benzofurans,  18  (3): [10.1007/s00044-008-9120-5]

Source

Source(1):

• Scientific Literature