3-(2,5-dimethoxyphenyl)-4-methyl-2-propyl-2,3-dihydropyrrolo[3,4-c]pyrrol-1(5H)-one

ID: ALA4066897

PubChem CID: 137633398

Max Phase: Preclinical

Molecular Formula: C18H22N2O3

Molecular Weight: 314.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1C(=O)c2c[nH]c(C)c2C1c1cc(OC)ccc1OC

Standard InChI:  InChI=1S/C18H22N2O3/c1-5-8-20-17(16-11(2)19-10-14(16)18(20)21)13-9-12(22-3)6-7-15(13)23-4/h6-7,9-10,17,19H,5,8H2,1-4H3

Standard InChI Key:  CHWGBKSAEUXZHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   10.5899  -15.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3850  -15.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9676  -14.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7557  -15.2340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4219  -14.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0923  -15.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8330  -16.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0088  -16.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5220  -16.6882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5033  -16.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1696  -16.0220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144  -15.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3991  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4219  -13.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1373  -13.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8485  -13.9230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5638  -13.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1373  -12.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4219  -12.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7108  -12.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9891  -12.2728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9891  -11.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7108  -13.5120    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
  6  7  1  0
  7  8  1  0
  4  8  1  0
  8  9  2  0
  7 10  2  0
 10 11  1  0
  6 12  2  0
 11 12  1  0
 12 13  1  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 14 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4066897

   ---

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: 314.39

Molecular Weight (Monoisotopic): 314.1630

AlogP: 3.30

#Rotatable Bonds: 5

Polar Surface Area: 54.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.86

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: -0.66

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