7-Allyl-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: ALA4089152

PubChem CID: 137644677

Max Phase: Preclinical

Molecular Formula: C21H22N4O3

Molecular Weight: 378.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1CC2=C(C1=O)C(c1ccc(C)cc1)c1c(n(CC)c(=O)[nH]c1=O)N2

Standard InChI:  InChI=1S/C21H22N4O3/c1-4-10-24-11-14-16(20(24)27)15(13-8-6-12(3)7-9-13)17-18(22-14)25(5-2)21(28)23-19(17)26/h4,6-9,15,22H,1,5,10-11H2,2-3H3,(H,23,26,28)

Standard InChI Key:  SGYUNIXZZZQROD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   26.1215  -15.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4165  -15.5033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7075  -15.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7075  -14.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4166  -13.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1215  -14.2775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0025  -13.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2934  -14.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2934  -15.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0025  -15.5033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0360  -14.6861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5162  -14.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5162  -15.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8306  -15.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4166  -13.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2615  -13.2456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0025  -13.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2934  -12.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0025  -11.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7075  -12.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2934  -11.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7075  -11.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0025  -10.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4165  -16.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1215  -16.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2188  -14.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8103  -15.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9931  -15.3910    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  2  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089152

   ---

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: 378.43

Molecular Weight (Monoisotopic): 378.1692

AlogP: 1.70

#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: 1.32

CX LogD: 1.32

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: -0.96

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