ethyl 3-cyclopropyl-4-(2-(pyridin-3-ylmethylamino)ethoxy)benzofuran-2-carboxylate

ID: ALA2262492

PubChem CID: 76326640

Max Phase: Preclinical

Molecular Formula: C22H24N2O4

Molecular Weight: 380.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1oc2cccc(OCCNCc3cccnc3)c2c1C1CC1

Standard InChI:  InChI=1S/C22H24N2O4/c1-2-26-22(25)21-19(16-8-9-16)20-17(6-3-7-18(20)28-21)27-12-11-24-14-15-5-4-10-23-13-15/h3-7,10,13,16,24H,2,8-9,11-12,14H2,1H3

Standard InChI Key:  MKDPXPFXOQKDMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.2181  -16.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328  -16.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9309  -15.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374  -15.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6462  -15.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426  -16.8272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9278  -16.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6898  -14.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7528  -16.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285  -14.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417  -14.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6392  -13.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524  -12.8524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3499  -12.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1693  -16.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9942  -16.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3991  -16.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0630  -11.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7799  -12.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926  -11.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4906  -10.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7699  -10.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0602  -10.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1612  -15.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3005  -14.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5151  -13.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  6  7  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
  9  5  2  0
  5 10  1  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 19 18  1  0
 16 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 11 26  2  0
 27 10  1  0
 28 27  1  0
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2262492

   Ethyl 3-cyclopropyl-4-[2-(pyridin-3-ylmethylamino)ethoxy]-1-benzofuran-2-carboxylate

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: 380.44

Molecular Weight (Monoisotopic): 380.1736

AlogP: 4.05

#Rotatable Bonds: 9

Polar Surface Area: 73.59

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.47

CX LogP: 3.18

CX LogD: 2.07

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.69

References

1. 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