5-(4-Methoxyphenyl)-1-methyl-5,9-dihydrofuro[3',4':5,6]pyrido-[2,3-d]pyrimidine-2,4,6(1H,3H,8H)-trione

ID: ALA4086263

PubChem CID: 137643147

Max Phase: Preclinical

Molecular Formula: C17H15N3O5

Molecular Weight: 341.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2C3=C(COC3=O)Nc3c2c(=O)[nH]c(=O)n3C)cc1

Standard InChI:  InChI=1S/C17H15N3O5/c1-20-14-13(15(21)19-17(20)23)11(8-3-5-9(24-2)6-4-8)12-10(18-14)7-25-16(12)22/h3-6,11,18H,7H2,1-2H3,(H,19,21,23)

Standard InChI Key:  RDJWSVQIOXAMKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   20.2096  -11.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4888  -12.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7877  -11.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8033  -10.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5200  -10.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2252  -11.0114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1023  -10.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3856  -10.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3699  -11.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0710  -12.1995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1139  -11.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6077  -10.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5875  -12.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9107  -12.2575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5357   -9.7694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3717   -9.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4732  -13.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1179   -9.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4168   -9.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4324   -8.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1491   -8.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8502   -8.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8346   -9.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1647   -7.2813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4637   -6.8562    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
  2 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 24 25  1  0
 21 24  1  0
  7 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086263

   ---

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: 341.32

Molecular Weight (Monoisotopic): 341.1012

AlogP: 0.45

#Rotatable Bonds: 2

Polar Surface Area: 102.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.59

CX Basic pKa: ┄

CX LogP: 0.30

CX LogD: 0.30

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -0.52

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