rac-6-(Cyclopentyloxy)-N-(2-fluorophenyl)-7-methoxy-1-phenyl-3,4-dihydroisoquinoline-3-carboxamide

ID: ALA4571089

PubChem CID: 155562866

Max Phase: Preclinical

Molecular Formula: C28H27FN2O3

Molecular Weight: 458.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC1CCCC1)CC(C(=O)Nc1ccccc1F)N=C2c1ccccc1

Standard InChI:  InChI=1S/C28H27FN2O3/c1-33-25-17-21-19(16-26(25)34-20-11-5-6-12-20)15-24(30-27(21)18-9-3-2-4-10-18)28(32)31-23-14-8-7-13-22(23)29/h2-4,7-10,13-14,16-17,20,24H,5-6,11-12,15H2,1H3,(H,31,32)

Standard InChI Key:  QYPKAMIHWGABOJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   27.0492  -22.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0479  -23.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7627  -24.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7609  -22.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4762  -22.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4796  -23.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1987  -24.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9189  -23.6078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9155  -22.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1919  -22.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2009  -24.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3347  -22.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3345  -21.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3333  -24.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6192  -23.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0076  -21.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7525  -20.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9275  -20.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6729  -21.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6287  -22.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3443  -22.7704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6261  -21.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0574  -22.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7726  -22.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4852  -22.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4831  -21.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7625  -21.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0528  -21.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7740  -23.5929    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.4875  -25.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4897  -26.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2053  -26.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9187  -26.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9165  -25.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
  1 12  1  0
 12 13  1  0
  2 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 13  1  0
  9 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 24 29  1  0
 11 30  1  0
 11 34  2  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4571089

   ---

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: 458.53

Molecular Weight (Monoisotopic): 458.2006

AlogP: 5.56

#Rotatable Bonds: 6

Polar Surface Area: 59.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.24

CX Basic pKa: 2.86

CX LogP: 6.02

CX LogD: 6.02

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.53

Np Likeness Score: -0.41

References

1. Liao Y, Jia X, Tang Y, Li S, Zang Y, Wang L, Cui ZN, Song G..  (2019)  Discovery of novel inhibitors of phosphodiesterase 4 with 1-phenyl-3,4-dihydroisoquinoline scaffold: Structure-based drug design and fragment identification.,  29  (22): [PMID:31610942] [10.1016/j.bmcl.2019.126720]

Source

Source(1):

• Scientific Literature