trans-2-amino-5-(-4-((S)-5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohexyl)nicotinonitrile

ID: ALA3099718

PubChem CID: 72724967

Max Phase: Preclinical

Molecular Formula: C23H26N4O2

Molecular Weight: 390.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC(=O)N([C@H]2CC[C@H](c3cnc(N)c(C#N)c3)CC2)[C@H]1c1ccccc1

Standard InChI:  InChI=1S/C23H26N4O2/c1-23(2)20(16-6-4-3-5-7-16)27(22(28)29-23)19-10-8-15(9-11-19)18-12-17(13-24)21(25)26-14-18/h3-7,12,14-15,19-20H,8-11H2,1-2H3,(H2,25,26)/t15-,19-,20-/m0/s1

Standard InChI Key:  SOHHQHWGZGODEC-YSSFQJQWSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    5.4245   -0.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9546   -1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6470   -2.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067   -3.2906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390   -2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -3.7801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.5045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945    3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2328    3.6062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943    3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    5.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8900    6.4533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -0.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2501    0.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2134    1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6300    3.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862    3.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1259    2.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7093    0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  8  1  0
 11 14  1  6
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 14  1  0
 19 21  1  0
 21 22  3  0
  7 23  1  0
 23  2  1  0
 23 24  1  1
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3099718

   2-amino-5-[4-[(4S)-5,5-dimethyl-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]cyclohexyl]pyridine-3-carbonitrile

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: 390.49

Molecular Weight (Monoisotopic): 390.2056

AlogP: 4.53

#Rotatable Bonds: 3

Polar Surface Area: 92.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.48

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.83

Np Likeness Score: -0.16

References

1. Huang H, Guzman-Perez A, Acquaviva L, Berry V, Bregman H, Dovey J, Gunaydin H, Huang X, Huang L, Saffran D, Serafino R, Schneider S, Wilson C, DiMauro EF..  (2013)  Structure-based design of 2-aminopyridine oxazolidinones as potent and selective tankyrase inhibitors.,  4  (12): [PMID:24900633] [10.1021/ml4003315]

2.  (2016)  Oxazolidinone compounds and derivatives thereof, 

Source

Source(2):

• Scientific Literature
• BindingDB Database