2-(4-chlorobenzoyl)-N-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide

ID: ALA4849116

PubChem CID: 164610524

Max Phase: Preclinical

Molecular Formula: C23H19ClN2O3

Molecular Weight: 406.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(O)c1)C1c2ccccc2CCN1C(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C23H19ClN2O3/c24-17-10-8-16(9-11-17)23(29)26-13-12-15-4-1-2-7-20(15)21(26)22(28)25-18-5-3-6-19(27)14-18/h1-11,14,21,27H,12-13H2,(H,25,28)

Standard InChI Key:  MEFGFBXAHZTNTE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   26.7554  -25.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7543  -25.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4623  -26.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4605  -24.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1691  -25.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1699  -25.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8784  -26.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5867  -25.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5820  -25.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8729  -24.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8801  -27.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1733  -27.5969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5887  -27.5940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1750  -28.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4665  -28.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4678  -29.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1769  -30.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8861  -29.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8813  -28.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5961  -30.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2960  -26.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2992  -27.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0021  -25.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7086  -26.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4142  -25.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4115  -25.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6972  -24.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9945  -25.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1170  -24.7226    0.0000 Cl  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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
  7 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
  8 21  1  0
 21 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
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4849116

   ---

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: 406.87

Molecular Weight (Monoisotopic): 406.1084

AlogP: 4.42

#Rotatable Bonds: 3

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 4.45

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.92

References

1. Sim S, Lee S, Ko S, Phuong Bui B, Linh Nguyen P, Cho J, Lee K, Kang JS, Jung JK, Lee H..  (2021)  Design, synthesis, and biological evaluation of potent 1,2,3,4-tetrahydroisoquinoline derivatives as anticancer agents targeting NF-κB signaling pathway.,  46  [PMID:34500188] [10.1016/j.bmc.2021.116371]

Source

Source(1):

• Scientific Literature