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

ID: ALA4066935

PubChem CID: 137632087

Max Phase: Preclinical

Molecular Formula: C19H17N3O4

Molecular Weight: 351.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C2C3=C(COC3=O)Nc3c2c(=O)[nH]c(=O)n3C2CC2)cc1

Standard InChI:  InChI=1S/C19H17N3O4/c1-9-2-4-10(5-3-9)13-14-12(8-26-18(14)24)20-16-15(13)17(23)21-19(25)22(16)11-6-7-11/h2-5,11,13,20H,6-8H2,1H3,(H,21,23,25)

Standard InChI Key:  ZEFGFAQVPMQFOV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   10.4345  -13.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7293  -13.9190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0205  -13.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0128  -12.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7180  -12.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4309  -12.6907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3040  -12.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988  -12.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6023  -13.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3153  -13.9282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3453  -13.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8192  -12.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275  -13.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1433  -13.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7145  -11.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5614  -11.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2963  -11.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5876  -11.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2892   -9.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0016  -11.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5840  -10.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9980  -10.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2816   -9.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7328  -14.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480  -15.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3309  -15.4449    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
 24 25  1  0
 25 26  1  0
 24 26  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4066935

   ---

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: 351.36

Molecular Weight (Monoisotopic): 351.1219

AlogP: 1.55

#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: 9.88

CX Basic pKa: ┄

CX LogP: 1.44

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -0.71

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