rac-6-(Cyclopentyloxy)-7-methoxy-N,1-diphenyl-3,4-dihydroisoquinoline-3-carboxamide

ID: ALA4537270

PubChem CID: 155548709

Max Phase: Preclinical

Molecular Formula: C28H28N2O3

Molecular Weight: 440.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC1CCCC1)CC(C(=O)Nc1ccccc1)N=C2c1ccccc1

Standard InChI:  InChI=1S/C28H28N2O3/c1-32-25-18-23-20(17-26(25)33-22-14-8-9-15-22)16-24(28(31)29-21-12-6-3-7-13-21)30-27(23)19-10-4-2-5-11-19/h2-7,10-13,17-18,22,24H,8-9,14-16H2,1H3,(H,29,31)

Standard InChI Key:  NDHYRPVCUXDJEO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.0954   -5.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8102   -5.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8083   -4.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5236   -4.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2462   -5.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9664   -5.5644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9630   -4.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2393   -4.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2484   -6.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3821   -4.3287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3819   -3.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -5.9801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6667   -5.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6761   -4.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3917   -4.7270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6735   -3.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1048   -4.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8200   -4.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5327   -4.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5306   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8098   -3.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -3.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5350   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5372   -8.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2528   -8.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9662   -8.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9640   -7.2170    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
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  5 10  1  0
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  1 12  1  0
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  2 14  1  0
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 18 19  1  0
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  9 20  1  0
 20 21  1  0
 20 22  2  0
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 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 11 29  1  0
 11 33  2  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537270

   ---

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: 440.54

Molecular Weight (Monoisotopic): 440.2100

AlogP: 5.42

#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: 12.51

CX Basic pKa: 3.19

CX LogP: 5.87

CX LogD: 5.87

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: -0.13

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