cis-(S)-3-(-4-(6-amino-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohexyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

ID: ALA3099717

Max Phase: Preclinical

Molecular Formula: C26H29N5O2

Molecular Weight: 443.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC(=O)N([C@H]2CC[C@@H](c3cnc(N)c(-c4ncccn4)c3)CC2)[C@H]1c1ccccc1

Standard InChI:  InChI=1S/C26H29N5O2/c1-26(2)22(18-7-4-3-5-8-18)31(25(32)33-26)20-11-9-17(10-12-20)19-15-21(23(27)30-16-19)24-28-13-6-14-29-24/h3-8,13-17,20,22H,9-12H2,1-2H3,(H2,27,30)/t17-,20+,22-/m0/s1

Standard InChI Key:  QTAONPFQLNZKSD-WEYGHZABSA-N

Molfile:  

     RDKit          2D

 33 37  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    5.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886    6.0075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1838    7.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8824    8.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858    7.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905    5.9992    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  1
 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  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  7 27  1  0
 27  2  1  0
 27 28  1  1
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3099717

   ---

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: 443.55

Molecular Weight (Monoisotopic): 443.2321

AlogP: 5.12

#Rotatable Bonds: 4

Polar Surface Area: 94.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.98

CX LogP: 4.48

CX LogD: 4.46

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: -0.08

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