2-[(8-hydroxy-7-quinolyl)methyl]-3,4-dihydro-1H-isoquinoline-6,7-diol

ID: ALA5207286

PubChem CID: 168295899

Max Phase: Preclinical

Molecular Formula: C19H18N2O3

Molecular Weight: 322.36

Names and Identifiers

Canonical SMILES:  Oc1cc2c(cc1O)CN(Cc1ccc3cccnc3c1O)CC2

Standard InChI:  InChI=1S/C19H18N2O3/c22-16-8-13-5-7-21(11-15(13)9-17(16)23)10-14-4-3-12-2-1-6-20-18(12)19(14)24/h1-4,6,8-9,22-24H,5,7,10-11H2

Standard InChI Key:  CGFGCVARRDNPQV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.4239    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4221   -1.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385   -1.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4221   -2.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8540   -1.4469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -1.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736   -0.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8591    0.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0025   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -1.0307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4318    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4318   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    1.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    1.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    1.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    0.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    2.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    1.4462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  5  7  1  0
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  9  8  2  0
 10  9  1  0
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  1 11  1  0
  4 12  1  0
 12 13  1  0
 14 13  1  0
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 16 15  2  0
 17 16  1  0
 18 17  1  0
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 15 19  1  0
 20 19  2  0
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 22 21  2  0
 16 22  1  0
 20 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5207286

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 322.36

Molecular Weight (Monoisotopic): 322.1317

AlogP: 2.91

#Rotatable Bonds: 2

Polar Surface Area: 76.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.47

CX Basic pKa: 8.39

CX LogP: 2.37

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.61

References

1. Pape VFS, Palkó R, Tóth S, Szabó MJ, Sessler J, Dormán G, Enyedy ÉA, Soós T, Szatmári I, Szakács G..  (2022)  Structure-Activity Relationships of 8-Hydroxyquinoline-Derived Mannich Bases with Tertiary Amines Targeting Multidrug-Resistant Cancer.,  65  (11.0): [PMID:35613553] [10.1021/acs.jmedchem.2c00076]

Source

Source(1):

• Scientific Literature