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

ID: ALA4094028

Cas Number: 848178-89-2

PubChem CID: 4800411

Max Phase: Preclinical

Molecular Formula: C17H15N3O4

Molecular Weight: 325.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2c(c(=O)[nH]c1=O)C(c1ccccc1)C1=C(COC1=O)N2

Standard InChI:  InChI=1S/C17H15N3O4/c1-2-20-14-13(15(21)19-17(20)23)11(9-6-4-3-5-7-9)12-10(18-14)8-24-16(12)22/h3-7,11,18H,2,8H2,1H3,(H,19,21,23)

Standard InChI Key:  WMTVHKOJALQDKD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   19.2135  -19.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5055  -20.4015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7913  -19.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7830  -19.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4909  -18.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2073  -19.1632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0666  -18.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3628  -19.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3711  -20.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0833  -20.4170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1022  -19.6094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5787  -18.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5926  -20.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9298  -20.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4826  -17.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3160  -18.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0583  -17.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3482  -17.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3399  -16.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0437  -16.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7601  -16.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7663  -17.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5139  -21.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2281  -21.6235    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
 23 24  1  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094028

   1-ethyl-5-phenyl-5,9-dihydrofuro[3',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H,8H)-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: 325.32

Molecular Weight (Monoisotopic): 325.1063

AlogP: 0.92

#Rotatable Bonds: 2

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: 9.88

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: 0.81

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.70

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