1-Cyclopropyl-7-((3,5-difluoro-4-hydroxyphenyl)amino)-4,4-dimethyl-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-2-one

ID: ALA4866663

PubChem CID: 164625612

Max Phase: Preclinical

Molecular Formula: C18H18F2N4O3

Molecular Weight: 376.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C1OC(=O)N(C2CC2)c2nc(Nc3cc(F)c(O)c(F)c3)ncc21

Standard InChI:  InChI=1S/C18H18F2N4O3/c1-8(2)15-11-7-21-17(22-9-5-12(19)14(25)13(20)6-9)23-16(11)24(10-3-4-10)18(26)27-15/h5-8,10,15,25H,3-4H2,1-2H3,(H,21,22,23)

Standard InChI Key:  FAHNZDGABWTKJF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.3159  -16.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1972  -16.7441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1960  -17.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041  -17.9726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023  -16.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6109  -16.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143  -17.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3267  -17.9731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402  -17.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369  -16.7347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880  -17.9717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874  -18.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813  -19.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803  -20.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882  -20.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1986  -20.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961  -19.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491  -17.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289  -18.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3094  -15.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0138  -15.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984  -15.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074  -20.4196    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721  -20.4231    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4886  -21.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256  -19.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428  -19.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6  1  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  1  1  0
  3 11  1  0
 11 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
  9 18  2  0
  8 19  1  0
  1 20  1  0
 20 21  1  0
 20 22  1  0
 16 23  1  0
 14 24  1  0
 15 25  1  0
 26 19  1  0
 27 26  1  0
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866663

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.36

Molecular Weight (Monoisotopic): 376.1347

AlogP: 4.02

#Rotatable Bonds: 4

Polar Surface Area: 87.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.28

CX Basic pKa: 1.59

CX LogP: 3.99

CX LogD: 3.93

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.61

References

1. Yuan Y, Xu J, Jiang L, Yu K, Ge Y, Li M, He H, Niu Q, Shi X, Fan L, Chen Z, Zhao Z, Li S, Xu Y, Wang Z, Li H..  (2021)  Discovery, Optimization, and Structure-Activity Relationship Study of Novel and Potent RSK4 Inhibitors as Promising Agents for the Treatment of Esophageal Squamous Cell Carcinoma.,  64  (18.0): [PMID:34496560] [10.1021/acs.jmedchem.1c00969]

Source

Source(1):

• Scientific Literature