1-Ethyl-7-(4-hydroxyphenethyl)-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: ALA4085204

PubChem CID: 137648257

Max Phase: Preclinical

Molecular Formula: C26H26N4O4

Molecular Weight: 458.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)[nH]c1=O)C(c1ccc(C)cc1)C1=C(CN(CCc3ccc(O)cc3)C1=O)N2

Standard InChI:  InChI=1S/C26H26N4O4/c1-3-30-23-22(24(32)28-26(30)34)20(17-8-4-15(2)5-9-17)21-19(27-23)14-29(25(21)33)13-12-16-6-10-18(31)11-7-16/h4-11,20,27,31H,3,12-14H2,1-2H3,(H,28,32,34)

Standard InChI Key:  VLSYQVCLFAZVNI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   19.3373  -13.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6282  -14.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9191  -13.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9191  -12.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6282  -12.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3373  -12.7777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2100  -12.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4968  -12.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4968  -13.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2100  -14.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2353  -13.1863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7195  -12.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7195  -13.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0463  -14.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6282  -11.5478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4649  -11.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.9191  -11.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4968  -10.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9191  -10.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2100   -9.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4140  -13.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0054  -13.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1890  -13.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7804  -14.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9590  -14.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5504  -13.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9590  -13.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7804  -13.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7291  -13.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6282  -14.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3373  -15.2376    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
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  8 12  1  0
  9 13  1  0
  3 10  1  0
  4  7  1  0
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  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
 29 32  1  0
 11 24  1  0
 33 34  1  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085204

   ---

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: 458.52

Molecular Weight (Monoisotopic): 458.1954

AlogP: 2.47

#Rotatable Bonds: 5

Polar Surface Area: 107.43

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.35

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.54

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