1-Ethyl-5-(p-tolyl)-5,7,8,9-tetrahydro-1H-cyclopenta[5,6]pyrido-[2,3-d]pyrimidine-2,4,6(3H)-trione

ID: ALA4093510

PubChem CID: 137654718

Max Phase: Preclinical

Molecular Formula: C19H19N3O3

Molecular Weight: 337.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)[nH]c1=O)C(c1ccc(C)cc1)C1=C(CCC1=O)N2

Standard InChI:  InChI=1S/C19H19N3O3/c1-3-22-17-16(18(24)21-19(22)25)14(11-6-4-10(2)5-7-11)15-12(20-17)8-9-13(15)23/h4-7,14,20H,3,8-9H2,1-2H3,(H,21,24,25)

Standard InChI Key:  GFYQCHZFSLHBOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   14.0478  -12.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402  -13.1537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6338  -12.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6350  -11.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3468  -11.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0532  -11.9326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9287  -11.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2210  -11.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2156  -12.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9220  -13.1485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4409  -12.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9610  -12.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4455  -11.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7542  -13.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3480  -10.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1959  -10.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9340  -10.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2276  -10.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9406   -9.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6458  -10.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2330   -9.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6470   -9.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9460   -8.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3348  -13.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0412  -14.3841    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
 12 13  1  0
  8 13  1  0
  9 11  1  0
  3 10  1  0
  4  7  1  0
  1 14  2  0
  5 15  2  0
 13 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
M  END

Alternative Forms

1. Parent:

   

   ALA4093510

   ---

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: 337.38

Molecular Weight (Monoisotopic): 337.1426

AlogP: 2.04

#Rotatable Bonds: 2

Polar Surface Area: 83.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.88

CX Basic pKa: ┄

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: -0.95

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