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

ID: ALA4066490

Cas Number: 863668-69-3

PubChem CID: 16251975

Max Phase: Preclinical

Molecular Formula: C16H13N3O4

Molecular Weight: 311.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c2c(c(=O)[nH]c1=O)C(c1ccccc1)C1=C(COC1=O)N2

Standard InChI:  InChI=1S/C16H13N3O4/c1-19-13-12(14(20)18-16(19)22)10(8-5-3-2-4-6-8)11-9(17-13)7-23-15(11)21/h2-6,10,17H,7H2,1H3,(H,18,20,22)

Standard InChI Key:  LDRPHFMYAJCBFM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   19.3293  -19.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6243  -19.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9152  -19.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9152  -18.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6243  -18.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3293  -18.6402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2061  -18.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4970  -18.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4970  -19.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2061  -19.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2438  -19.0488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7239  -18.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7239  -19.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0383  -19.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6243  -17.4144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4693  -17.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2061  -17.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4970  -17.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4970  -16.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2061  -15.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9152  -16.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9152  -17.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6243  -20.6831    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
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
  7 17  1  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4066490

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

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: 311.30

Molecular Weight (Monoisotopic): 311.0906

AlogP: 0.44

#Rotatable Bonds: 1

Polar Surface Area: 93.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.59

CX Basic pKa: ┄

CX LogP: 0.46

CX LogD: 0.45

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.58

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