1-Ethyl-5-(p-tolyl)furo[3',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6-(1H,3H,8H)-trione

ID: ALA4067951

PubChem CID: 137632690

Max Phase: Preclinical

Molecular Formula: C18H15N3O4

Molecular Weight: 337.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c(=O)[nH]c(=O)c2c(-c3ccc(C)cc3)c3c(nc21)COC3=O

Standard InChI:  InChI=1S/C18H15N3O4/c1-3-21-15-14(16(22)20-18(21)24)12(10-6-4-9(2)5-7-10)13-11(19-15)8-25-17(13)23/h4-7H,3,8H2,1-2H3,(H,20,22,24)

Standard InChI Key:  XQIVSOWGERBFQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   13.0085  -12.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3114  -12.9006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5948  -12.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5795  -11.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2766  -11.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9932  -11.6589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8630  -11.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1617  -11.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1770  -12.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8936  -12.9249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9124  -12.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3816  -11.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4073  -12.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7250  -12.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2613  -10.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1128  -10.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477  -10.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1311  -10.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8171   -8.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5448  -10.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1158   -9.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5295   -9.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8018   -8.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3267  -13.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0391  -14.1098    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  1  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  2  0
  4  7  2  0
  1 14  2  0
  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
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067951

   ---

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: 337.34

Molecular Weight (Monoisotopic): 337.1063

AlogP: 1.75

#Rotatable Bonds: 2

Polar Surface Area: 94.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: 0.03

CX LogP: 2.14

CX LogD: 2.13

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

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