trans-(S)-3-(-4-(6-aminopyridin-3-yl)cyclohexyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

ID: ALA3098146

PubChem CID: 72724968

Max Phase: Preclinical

Molecular Formula: C22H27N3O2

Molecular Weight: 365.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC(=O)N([C@H]2CC[C@H](c3ccc(N)nc3)CC2)[C@H]1c1ccccc1

Standard InChI:  InChI=1S/C22H27N3O2/c1-22(2)20(16-6-4-3-5-7-16)25(21(26)27-22)18-11-8-15(9-12-18)17-10-13-19(23)24-14-17/h3-7,10,13-15,18,20H,8-9,11-12H2,1-2H3,(H2,23,24)/t15-,18-,20-/m0/s1

Standard InChI Key:  UJGMIJUNDOEIIP-QSFXBCCZSA-N

Molfile:  

     RDKit          2D

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   26.1542  -10.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1629  -11.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8153  -12.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8142  -12.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5290  -13.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2455  -12.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2425  -12.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5272  -11.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9570  -13.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9569  -14.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6713  -14.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3860  -14.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3821  -13.2445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6672  -12.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1469  -11.5310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1382  -10.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3510  -10.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3650  -11.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1017  -14.4841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8005  -10.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9739  -12.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1501  -12.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7596  -13.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1936  -13.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0225  -13.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4093  -13.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  7 10  1  1
 16 17  1  0
 17 18  1  0
 18  1  1  0
  1 19  1  0
 19 16  1  0
  4 16  1  6
 13 20  1  0
 17 21  2  0
 19 22  1  1
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3098146

   (4S)-3-[4-(6-aminopyridin-3-yl)cyclohexyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

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: 365.48

Molecular Weight (Monoisotopic): 365.2103

AlogP: 4.66

#Rotatable Bonds: 3

Polar Surface Area: 68.45

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.09

CX LogP: 4.11

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.86

Np Likeness Score: 0.35

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]

Source

Source(1):

• Scientific Literature