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

ID: ALA4085767

PubChem CID: 137643820

Max Phase: Preclinical

Molecular Formula: C19H19N3O4

Molecular Weight: 353.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)n(C)c1=O)C(c1ccc(C)cc1)C1=C(COC1=O)N2

Standard InChI:  InChI=1S/C19H19N3O4/c1-4-22-16-15(17(23)21(3)19(22)25)13(11-7-5-10(2)6-8-11)14-12(20-16)9-26-18(14)24/h5-8,13,20H,4,9H2,1-3H3

Standard InChI Key:  UVXLCDRWDGHQDE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   22.3875  -15.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6826  -15.9634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9735  -15.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9735  -14.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6826  -14.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3875  -14.7377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644  -14.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5553  -14.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5553  -15.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644  -15.9634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3021  -15.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7822  -14.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7822  -15.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0966  -15.9634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6826  -13.5119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5275  -13.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644  -13.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5553  -13.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644  -11.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9735  -13.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5553  -12.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9735  -12.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644  -11.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0966  -14.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6826  -16.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3875  -17.1892    0.0000 C   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
 17 20  2  0
 18 21  2  0
 19 21  1  0
 19 22  2  0
 20 22  1  0
 19 23  1  0
  7 17  1  0
  6 24  1  0
 25 26  1  0
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085767

   ---

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: 353.38

Molecular Weight (Monoisotopic): 353.1376

AlogP: 1.24

#Rotatable Bonds: 2

Polar Surface Area: 82.33

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.23

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: -0.68

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