1-Ethyl-7-phenethyl-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: ALA4092949

PubChem CID: 137653484

Max Phase: Preclinical

Molecular Formula: C26H26N4O3

Molecular Weight: 442.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)[nH]c1=O)C(c1ccc(C)cc1)C1=C(CN(CCc3ccccc3)C1=O)N2

Standard InChI:  InChI=1S/C26H26N4O3/c1-3-30-23-22(24(31)28-26(30)33)20(18-11-9-16(2)10-12-18)21-19(27-23)15-29(25(21)32)14-13-17-7-5-4-6-8-17/h4-12,20,27H,3,13-15H2,1-2H3,(H,28,31,33)

Standard InChI Key:  DQFBZYXAVHHSEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   21.6420  -14.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9288  -15.2995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2197  -14.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2197  -14.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9288  -13.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6420  -14.0696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5106  -13.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8015  -14.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8015  -14.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5106  -15.2995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5400  -14.4823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0201  -13.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0201  -15.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3511  -15.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9288  -12.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7655  -13.0377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5106  -12.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8015  -12.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5106  -11.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2197  -12.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8015  -11.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2197  -11.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5106  -10.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7187  -14.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3101  -15.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4888  -15.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0802  -15.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2588  -15.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8502  -15.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2588  -14.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0802  -14.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9288  -16.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6420  -16.5294    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
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 11 24  1  0
 32 33  1  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092949

   ---

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: 442.52

Molecular Weight (Monoisotopic): 442.2005

AlogP: 2.76

#Rotatable Bonds: 5

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: 2.60

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.64

Np Likeness Score: -0.90

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