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

ID: ALA4088746

Cas Number: 871548-03-7

PubChem CID: 16258758

Max Phase: Preclinical

Molecular Formula: C18H17N3O4

Molecular Weight: 339.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c2c(c(=O)[nH]c1=O)C(c1ccccc1)C1=C(COC1=O)N2

Standard InChI:  InChI=1S/C18H17N3O4/c1-2-8-21-15-14(16(22)20-18(21)24)12(10-6-4-3-5-7-10)13-11(19-15)9-25-17(13)23/h3-7,12,19H,2,8-9H2,1H3,(H,20,22,24)

Standard InChI Key:  JXTZQNJRSYNAJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   29.4065  -18.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7127  -18.4641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9935  -18.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9681  -17.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6619  -16.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3853  -17.2188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2488  -16.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5550  -17.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5763  -18.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2997  -18.5089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3092  -17.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7667  -17.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8113  -18.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1258  -18.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6365  -16.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4927  -16.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7382  -19.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4574  -19.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4828  -20.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2234  -16.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5042  -15.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4788  -14.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1726  -14.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8959  -14.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9172  -15.6263    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  1  0
  2 17  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
  7 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088746

   CID 16258758

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: 339.35

Molecular Weight (Monoisotopic): 339.1219

AlogP: 1.31

#Rotatable Bonds: 3

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: 1.34

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: -0.77

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