7-Benzyl-1-ethyl-5-(p-tolyl)-5,7,8,9-tetrahydro-1H-pyrrolo-[3',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione

ID: ALA4065286

PubChem CID: 137632577

Max Phase: Preclinical

Molecular Formula: C25H24N4O3

Molecular Weight: 428.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)[nH]c1=O)C(c1ccc(C)cc1)C1=C(CN(Cc3ccccc3)C1=O)N2

Standard InChI:  InChI=1S/C25H24N4O3/c1-3-29-22-21(23(30)27-25(29)32)19(17-11-9-15(2)10-12-17)20-18(26-22)14-28(24(20)31)13-16-7-5-4-6-8-16/h4-12,19,26H,3,13-14H2,1-2H3,(H,27,30,32)

Standard InChI Key:  ZBRDRGVJFCJFQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   14.7093  -14.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0002  -14.8840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2952  -14.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2952  -13.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0002  -13.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7093  -13.6582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861  -13.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8770  -13.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8770  -14.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861  -14.8840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6197  -14.0668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0998  -13.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0998  -14.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4183  -14.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0002  -12.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8493  -12.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861  -12.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8770  -12.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861  -10.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2952  -12.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8770  -11.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2952  -11.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861   -9.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0002  -15.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7093  -16.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8025  -14.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3939  -14.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8025  -15.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3939  -16.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5767  -16.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1681  -15.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5767  -14.7717    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
  2 24  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 27 32  2  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4065286

   ---

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: 428.49

Molecular Weight (Monoisotopic): 428.1848

AlogP: 2.72

#Rotatable Bonds: 4

Polar Surface Area: 87.20

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.88

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.67

Np Likeness Score: -1.05

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