(E)-3-(2-ethylbutylidene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one

ID: ALA5205514

PubChem CID: 164880785

Max Phase: Preclinical

Molecular Formula: C17H20N2O

Molecular Weight: 268.36

Names and Identifiers

Canonical SMILES:  CCC(/C=C1\CCn2c1nc(=O)c1ccccc12)CC

Standard InChI:  InChI=1S/C17H20N2O/c1-3-12(4-2)11-13-9-10-19-15-8-6-5-7-14(15)17(20)18-16(13)19/h5-8,11-12H,3-4,9-10H2,1-2H3/b13-11+

Standard InChI Key:  HQQMGQIBANBVES-ACCUITESSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -3.1177    0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4032    1.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913    0.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913    0.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1177    0.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766   -0.2831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2620    0.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2620    0.9546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    2.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -1.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982   -1.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537   -0.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -0.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5343   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -1.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1177   -1.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071   -2.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 14 13  1  0
  7 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 17 19  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5205514

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 268.36

Molecular Weight (Monoisotopic): 268.1576

AlogP: 3.62

#Rotatable Bonds: 3

Polar Surface Area: 34.89

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.88

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.85

Np Likeness Score: -0.05

References

1. Shishodia S, Nuñez R, Strohmier BP, Bursch KL, Goetz CJ, Olp MD, Jensen DR, Fenske TG, Ordonez-Rubiano SC, Blau ME, Roach MK, Peterson FC, Volkman BF, Dykhuizen EC, Smith BC..  (2022)  Selective and Cell-Active PBRM1 Bromodomain Inhibitors Discovered through NMR Fragment Screening.,  65  (20.0): [PMID:36227159] [10.1021/acs.jmedchem.2c00864]

Source

Source(1):

• Scientific Literature