(R)-4-Methoxy-14-methyl-7,8,13b,14-tetrahydroindolo-[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one

ID: ALA4760741

PubChem CID: 162658144

Max Phase: Preclinical

Molecular Formula: C20H19N3O2

Molecular Weight: 333.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)N1CCc3c([nH]c4ccccc34)[C@@H]1N2C

Standard InChI:  InChI=1S/C20H19N3O2/c1-22-15-8-5-9-16(25-2)17(15)20(24)23-11-10-13-12-6-3-4-7-14(12)21-18(13)19(22)23/h3-9,19,21H,10-11H2,1-2H3/t19-/m1/s1

Standard InChI Key:  AVLFPUHBJIXSIY-LJQANCHMSA-N

Molfile:  

 
     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   14.0514   -8.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7081   -9.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1811  -10.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8378  -10.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3067  -11.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1190  -11.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4623  -10.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9933   -9.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3367   -9.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1530   -9.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0214  -10.8740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6781  -11.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5525  -10.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8958   -9.4602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4269   -8.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6105   -8.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7361  -10.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2672   -9.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4884   -9.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848   -9.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0705   -9.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0599  -10.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7594  -11.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4737  -10.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2491  -10.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1439  -10.9088    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 19 24  1  0
 24 25  1  0
 17 25  1  0
 13 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4760741

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 333.39

Molecular Weight (Monoisotopic): 333.1477

AlogP: 3.32

#Rotatable Bonds: 1

Polar Surface Area: 48.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: 0.28

References

1. Zhang T,Lai Z,Yuan S,Huang YY,Dong G,Sheng C,Ke H,Luo HB.  (2020)  Discovery of Evodiamine Derivatives as Highly Selective PDE5 Inhibitors Targeting a Unique Allosteric Pocket.,  63  (17): [PMID:32794708] [10.1021/acs.jmedchem.0c00983]

Source

Source(1):

• Scientific Literature