1-Ethyl-5-(4-(trifluoromethyl)phenyl)-5,9-dihydrofuro[3',4':5,6]-pyrido[2,3-d]pyrimidine-2,4,6(1H,3H,8H)-trione

ID: ALA4094424

PubChem CID: 137655200

Max Phase: Preclinical

Molecular Formula: C18H14F3N3O4

Molecular Weight: 393.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)[nH]c1=O)C(c1ccc(C(F)(F)F)cc1)C1=C(COC1=O)N2

Standard InChI:  InChI=1S/C18H14F3N3O4/c1-2-24-14-13(15(25)23-17(24)27)11(12-10(22-14)7-28-16(12)26)8-3-5-9(6-4-8)18(19,20)21/h3-6,11,22H,2,7H2,1H3,(H,23,25,27)

Standard InChI Key:  GSQMKFKPHLJZSN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   12.5525  -12.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8433  -13.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1385  -12.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1427  -12.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8560  -11.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5609  -12.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4378  -11.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7287  -12.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7203  -12.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4293  -13.3850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4672  -12.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9541  -11.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9447  -13.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2573  -13.4017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8602  -10.9439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7074  -11.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4421  -10.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7372  -10.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7456   -9.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4547   -9.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1596   -9.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1554  -10.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4590   -8.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8391  -14.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5440  -14.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1688   -8.0771    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7534   -8.0698    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4543   -7.6643    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 12  1  0
 11 13  1  0
  8 12  1  0
  9 13  1  0
  3 10  1  0
  4  7  1  0
  1 14  2  0
  5 15  2  0
 12 16  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 20 23  1  0
  7 17  1  0
 24 25  1  0
  2 24  1  0
 23 26  1  0
 23 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094424

   ---

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: 393.32

Molecular Weight (Monoisotopic): 393.0936

AlogP: 1.94

#Rotatable Bonds: 2

Polar Surface Area: 93.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: ┄

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -0.91

References

1. Ayoub AM, Hawk LML, Herzig RJ, Jiang J, Wisniewski AJ, Gee CT, Zhao P, Zhu JY, Berndt N, Offei-Addo NK, Scott TG, Qi J, Bradner JE, Ward TR, Schönbrunn E, Georg GI, Pomerantz WCK..  (2017)  BET Bromodomain Inhibitors with One-Step Synthesis Discovered from Virtual Screen.,  60  (12): [PMID:28535045] [10.1021/acs.jmedchem.6b01336]

Source

Source(1):

• Scientific Literature