(S)-4-bromo-7-methoxy-1-((5-oxopyrrolidin-2-yl)methoxy)isoquinoline-6-carboxamide

ID: ALA4536517

PubChem CID: 155548286

Max Phase: Preclinical

Molecular Formula: C16H16BrN3O4

Molecular Weight: 394.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(OC[C@@H]3CCC(=O)N3)ncc(Br)c2cc1C(N)=O

Standard InChI:  InChI=1S/C16H16BrN3O4/c1-23-13-5-10-9(4-11(13)15(18)22)12(17)6-19-16(10)24-7-8-2-3-14(21)20-8/h4-6,8H,2-3,7H2,1H3,(H2,18,22)(H,20,21)/t8-/m0/s1

Standard InChI Key:  IPUGCJLTEYLCFC-QMMMGPOBSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.5439   -5.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -6.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2508   -6.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2490   -5.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9576   -5.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584   -6.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -6.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3752   -6.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3704   -5.5736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6613   -5.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686   -7.6238    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6570   -4.3531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -3.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3582   -3.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0152   -2.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7586   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9413   -1.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6930   -2.6489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4574   -1.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -5.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -4.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8347   -6.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -6.4025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340   -7.6289    0.0000 O   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  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  7 11  1  0
 10 12  1  0
 12 13  1  0
 14 13  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 17 19  2  0
  1 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536517

   ---

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: 394.23

Molecular Weight (Monoisotopic): 393.0324

AlogP: 1.76

#Rotatable Bonds: 5

Polar Surface Area: 103.54

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.87

CX Basic pKa: 0.80

CX LogP: 0.95

CX LogD: 0.95

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.28

References

1. Nunes J, McGonagle GA, Eden J, Kiritharan G, Touzet M, Lewell X, Emery J, Eidam H, Harling JD, Anderson NA..  (2019)  Targeting IRAK4 for Degradation with PROTACs.,  10  (7): [PMID:31312412] [10.1021/acsmedchemlett.9b00219]

Source

Source(1):

• Scientific Literature