3'-(5-((1H-indol-3-yl)methyl)-1,2,4-oxadiazol-3-yl)biphenyl-4-ol

ID: ALA3759694

PubChem CID: 127027703

Max Phase: Preclinical

Molecular Formula: C23H17N3O2

Molecular Weight: 367.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2cccc(-c3noc(Cc4c[nH]c5ccccc45)n3)c2)cc1

Standard InChI:  InChI=1S/C23H17N3O2/c27-19-10-8-15(9-11-19)16-4-3-5-17(12-16)23-25-22(28-26-23)13-18-14-24-21-7-2-1-6-20(18)21/h1-12,14,24,27H,13H2

Standard InChI Key:  JCGGXQINPNNNIK-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
    8.6896   -2.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0047   -2.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -0.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7552    0.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4400   -0.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2877   -2.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2573   -4.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5409   -5.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8549   -4.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8853   -2.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6017   -2.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8817   -5.0394    0.0000 O   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
  5  1  2  0
  4  6  1  0
  6  7  2  0
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  9 10  1  0
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 11  6  1  0
  8 12  1  0
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 15 16  1  0
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 15 18  1  0
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 20 19  1  0
 21 20  2  0
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 24 23  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 28 23  1  0
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3759694

   ---

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: 367.41

Molecular Weight (Monoisotopic): 367.1321

AlogP: 5.18

#Rotatable Bonds: 4

Polar Surface Area: 74.94

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.86

CX Basic pKa: ┄

CX LogP: 5.66

CX LogD: 5.66

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -0.95

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