5-(6-amino-4-ethyl-5-(4-hydroxyphenyl)pyridin-3-yl)-2-hydroxybenzonitrile

ID: ALA5287657

Max Phase: Preclinical

Molecular Formula: C20H17N3O2

Molecular Weight: 331.38

Names and Identifiers

Canonical SMILES:  CCc1c(-c2ccc(O)c(C#N)c2)cnc(N)c1-c1ccc(O)cc1

Standard InChI:  InChI=1S/C20H17N3O2/c1-2-16-17(13-5-8-18(25)14(9-13)10-21)11-23-20(22)19(16)12-3-6-15(24)7-4-12/h3-9,11,24-25H,2H2,1H3,(H2,22,23)

Standard InChI Key:  WYGBKDFNBQHHND-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.7874    1.4469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    0.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7889   -0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7889   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5067   -1.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -1.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337   -1.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049    0.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -1.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761   -1.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    1.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559    1.4471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7849   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5022   -1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180   -1.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5022   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9337    0.6221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10  4  2  0
 11  3  2  0
 11 12  1  0
 12 13  1  0
 14 11  1  0
 15 14  2  0
 16 15  1  0
  2 16  2  0
 14 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 20 21  1  0
 22 20  1  0
 22 23  2  0
 17 23  1  0
 24 22  1  0
 24 25  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287657

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 331.38

Molecular Weight (Monoisotopic): 331.1321

AlogP: 3.84

#Rotatable Bonds: 3

Polar Surface Area: 103.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.02

CX Basic pKa: 6.81

CX LogP: 3.74

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 0.06

References

1. Li P, Liu HM..  (2020)  Recent advances in the development of ubiquitin-specific-processing protease 7 (USP7) inhibitors.,  191  [PMID:32092586] [10.1016/j.ejmech.2020.112107]

Source

Source(1):

• Scientific Literature