5-((1H-indol-3-yl)methyl)-3-(5-(4-ethoxyphenyl)thiophen-2-yl)-1,2,4-oxadiazole

ID: ALA3759414

PubChem CID: 127025576

Max Phase: Preclinical

Molecular Formula: C23H19N3O2S

Molecular Weight: 401.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(-c2ccc(-c3noc(Cc4c[nH]c5ccccc45)n3)s2)cc1

Standard InChI:  InChI=1S/C23H19N3O2S/c1-2-27-17-9-7-15(8-10-17)20-11-12-21(29-20)23-25-22(28-26-23)13-16-14-24-19-6-4-3-5-18(16)19/h3-12,14,24H,2,13H2,1H3

Standard InChI Key:  RVFLDTJBWMTXKQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.2542   -4.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7448   -4.1226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0456   -2.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7409   -1.9129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4119   -2.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7468   -2.6774    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7713   -1.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0460   -0.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5731   -0.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2606   -1.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9440   -3.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4422   -3.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2541   -1.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5676   -0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0694   -0.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7533   -1.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5638   -0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7625   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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  8 11  1  0
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 12 13  1  0
 13 14  2  0
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 14 17  1  0
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 18 19  1  0
 20  1  1  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 29 24  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3759414

   ---

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: 401.49

Molecular Weight (Monoisotopic): 401.1198

AlogP: 5.94

#Rotatable Bonds: 6

Polar Surface Area: 63.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 5.63

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.33

References

1. Zhang L, Jiang CS, Gao LX, Gong JX, Wang ZH, Li JY, Li J, Li XW, Guo YW..  (2016)  Design, synthesis and in vitro activity of phidianidine B derivatives as novel PTP1B inhibitors with specific selectivity.,  26  (3): [PMID:26774579] [10.1016/j.bmcl.2015.12.097]

Source

Source(1):

• Scientific Literature