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

ID: ALA3760059

PubChem CID: 127028347

Max Phase: Preclinical

Molecular Formula: C28H25N3O4

Molecular Weight: 467.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCCOc1ccc(-c2cccc(-c3noc(Cc4c[nH]c5ccccc45)n3)c2)cc1

Standard InChI:  InChI=1S/C28H25N3O4/c1-33-27(32)10-5-15-34-23-13-11-19(12-14-23)20-6-4-7-21(16-20)28-30-26(35-31-28)17-22-18-29-25-9-3-2-8-24(22)25/h2-4,6-9,11-14,16,18,29H,5,10,15,17H2,1H3

Standard InChI Key:  NZHGQSSPEOWUFK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   15.1408   -5.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4544   -4.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7403   -5.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0540   -4.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3398   -5.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6535   -4.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6816   -5.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3176   -6.4886    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
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 26  1  1  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  1  0
 31 30  2  0
 32 31  1  0
 33 32  2  0
 34 33  1  0
 35 34  2  0
 35 30  1  0
 27 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3760059

   ---

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: 467.53

Molecular Weight (Monoisotopic): 467.1845

AlogP: 5.81

#Rotatable Bonds: 9

Polar Surface Area: 90.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.82

CX LogD: 5.82

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.22

Np Likeness Score: -1.04

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