(+/-)-1-(2-(1H-Indol-3-yl)ethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-methanal

ID: ALA4556365

PubChem CID: 139399292

Max Phase: Preclinical

Molecular Formula: C22H24N2O3

Molecular Weight: 364.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(CCc1c[nH]c3ccccc13)N(C=O)CC2

Standard InChI:  InChI=1S/C22H24N2O3/c1-26-21-11-15-9-10-24(14-25)20(18(15)12-22(21)27-2)8-7-16-13-23-19-6-4-3-5-17(16)19/h3-6,11-14,20,23H,7-10H2,1-2H3

Standard InChI Key:  PIORUUQSJASDET-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.3653  -22.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641  -23.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790  -24.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0772  -22.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7925  -22.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7913  -23.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5043  -24.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2230  -23.6311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2242  -22.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5066  -22.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9363  -24.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6519  -23.6351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5020  -24.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2153  -25.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2130  -26.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5461  -26.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7989  -27.3767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8809  -26.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6230  -27.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1709  -27.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9767  -27.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2318  -27.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6822  -26.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506  -22.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505  -21.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6493  -24.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352  -23.6305    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  1  0
  8  9  1  0
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  7 13  1  0
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 17 19  1  0
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 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  1 24  1  0
 24 25  1  0
  2 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556365

   ---

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: 364.45

Molecular Weight (Monoisotopic): 364.1787

AlogP: 3.87

#Rotatable Bonds: 6

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: ┄

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: 0.47

References

1. Zhang X, Dong G, Li H, Chen W, Li J, Feng C, Gu Z, Zhu F, Zhang R, Li M, Tang W, Liu H, Xu Y..  (2019)  Structure-Aided Identification and Optimization of Tetrahydro-isoquinolines as Novel PDE4 Inhibitors Leading to Discovery of an Effective Antipsoriasis Agent.,  62  (11): [PMID:31099559] [10.1021/acs.jmedchem.9b00518]

Source

Source(1):

• Scientific Literature