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

ID: ALA2262496

PubChem CID: 76315759

Max Phase: Preclinical

Molecular Formula: C22H26N2O4

Molecular Weight: 382.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1oc2cccc(OCCNCc3cccnc3)c2c1C(C)C

Standard InChI:  InChI=1S/C22H26N2O4/c1-4-26-22(25)21-19(15(2)3)20-17(8-5-9-18(20)28-21)27-12-11-24-14-16-7-6-10-23-13-16/h5-10,13,15,24H,4,11-12,14H2,1-3H3

Standard InChI Key:  YMBGRJKDDSBICR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.5846  -25.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2995  -25.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2976  -24.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8043  -24.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0130  -24.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0155  -25.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8094  -25.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2947  -25.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2476  -23.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1197  -25.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951  -23.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0083  -23.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0059  -22.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7192  -21.7699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7166  -20.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5362  -25.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3612  -25.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7661  -25.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4299  -20.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1467  -20.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8595  -20.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8574  -19.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1367  -19.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4270  -19.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5281  -24.3463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0718  -23.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8668  -22.9721    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
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  5  6  1  0
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  9  5  2  0
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  9 11  1  0
  4 12  1  0
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 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
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 22 23  2  0
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 24 25  2  0
 25 20  1  0
 11 26  2  0
 10 27  1  0
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2262496

   Ethyl 3-propan-2-yl-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: 382.46

Molecular Weight (Monoisotopic): 382.1893

AlogP: 4.30

#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: 3.64

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -0.72

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