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

ID: ALA4758217

PubChem CID: 162656285

Max Phase: Preclinical

Molecular Formula: C19H17N3O2

Molecular Weight: 319.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1c2cccc(O)c2C(=O)N2CCc3c([nH]c4ccccc34)[C@H]21

Standard InChI:  InChI=1S/C19H17N3O2/c1-21-14-7-4-8-15(23)16(14)19(24)22-10-9-12-11-5-2-3-6-13(11)20-17(12)18(21)22/h2-8,18,20,23H,9-10H2,1H3/t18-/m0/s1

Standard InChI Key:  BKYCMCVWWVNOOP-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   13.4818   -7.9002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1385   -8.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6116   -9.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2682  -10.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7372  -10.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5494  -10.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8927   -9.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4238   -9.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7671   -8.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4519  -10.1269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1086  -10.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9829   -9.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3263   -8.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8573   -8.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0410   -8.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1666   -9.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6977   -8.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9189   -9.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2152   -8.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5009   -9.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4903   -9.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1899  -10.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9041   -9.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6795  -10.1824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5686  -10.1612    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
  4 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 18 23  1  0
 23 24  1  0
 16 24  1  0
 12 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4758217

   ---

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: 319.36

Molecular Weight (Monoisotopic): 319.1321

AlogP: 3.02

#Rotatable Bonds: ┄

Polar Surface Area: 59.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.62

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 0.49

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