2-tert-butoxy-2-(1-(3-methoxyphenyl)-3-phenylisoquinolin-4-yl)acetic acid

ID: ALA4558632

PubChem CID: 145999096

Max Phase: Preclinical

Molecular Formula: C28H27NO4

Molecular Weight: 441.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2nc(-c3ccccc3)c(C(OC(C)(C)C)C(=O)O)c3ccccc23)c1

Standard InChI:  InChI=1S/C28H27NO4/c1-28(2,3)33-26(27(30)31)23-21-15-8-9-16-22(21)24(19-13-10-14-20(17-19)32-4)29-25(23)18-11-6-5-7-12-18/h5-17,26H,1-4H3,(H,30,31)

Standard InChI Key:  SRHRYEHCDLVWME-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    5.4507  -18.4776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4495  -19.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8644  -18.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558  -18.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672  -19.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567  -19.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1552  -20.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8634  -20.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5746  -20.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5726  -19.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5705  -18.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2798  -18.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5675  -17.2455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2736  -16.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2706  -16.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9829  -17.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9767  -16.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2829  -19.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9860  -18.0574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7445  -19.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0364  -19.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3293  -19.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3289  -20.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416  -20.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7459  -20.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505  -17.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8586  -16.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8565  -16.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1471  -15.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4383  -16.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438  -16.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446  -21.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384  -22.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  3 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 12 18  2  0
 12 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  2 20  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
  4 26  1  0
 24 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558632

   ---

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: 441.53

Molecular Weight (Monoisotopic): 441.1940

AlogP: 6.52

#Rotatable Bonds: 6

Polar Surface Area: 68.65

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.23

CX Basic pKa: 3.47

CX LogP: 5.81

CX LogD: 3.14

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -0.39

References

1. Wilson TA, Koneru PC, Rebensburg SV, Lindenberger JJ, Kobe MJ, Cockroft NT, Adu-Ampratwum D, Larue RC, Kvaratskhelia M, Fuchs JR..  (2019)  An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors.,  10  (2): [PMID:30783506] [10.1021/acsmedchemlett.8b00633]

Source

Source(1):

• Scientific Literature