[14C]-6-tert-butyl-2-(2-(hydroxymethyl)-3-(1-methyl-5-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one

ID: ALA4098685

PubChem CID: 137659731

Max Phase: Preclinical

Molecular Formula: C36H39N5O5

Molecular Weight: 621.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cccc(N3CCc4cc(C(C)(C)C)ccc4C3=O)c2[14CH2]O)cc(Nc2ccc(C(=O)N3CCOCC3)cn2)c1=O

Standard InChI:  InChI=1S/C36H39N5O5/c1-36(2,3)26-9-10-28-23(18-26)12-13-41(34(28)44)31-7-5-6-27(29(31)22-42)25-19-30(35(45)39(4)21-25)38-32-11-8-24(20-37-32)33(43)40-14-16-46-17-15-40/h5-11,18-21,42H,12-17,22H2,1-4H3,(H,37,38)/i22+2

Standard InChI Key:  HCJJXHLWABHYMG-FSEIIBCTSA-N

Molfile:  

     RDKit          2D

 46 51  0  0  0  0  0  0  0  0999 V2000
    5.6902  -20.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6890  -21.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4038  -22.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1202  -21.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174  -20.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4020  -20.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8278  -20.4851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5436  -20.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5397  -19.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8226  -19.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2556  -19.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2514  -20.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9629  -20.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6791  -20.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6792  -19.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9670  -19.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5454  -21.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3995  -19.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1127  -19.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763  -20.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9781  -19.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676  -19.2534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5509  -19.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490  -20.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641  -20.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706  -18.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378  -19.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333  -20.8988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306  -21.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147  -22.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117  -22.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254  -23.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5435  -22.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430  -22.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3936  -19.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1081  -19.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3934  -18.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1040  -18.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239  -24.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086  -24.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375  -24.6077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5385  -25.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481  -25.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9657  -25.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9693  -24.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551  -24.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  7 10  1  0
  8 12  1  0
 11  9  1  0
  9 10  1  0
  5  7  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 17  2  0
  6 18  1  0
 18 19  1  0
 20 21  2  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
  1 20  1  0
 22 26  1  0
 23 27  2  0
 24 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 15 35  1  0
 35 36  1  0
 35 37  1  0
 35 38  1  0
 32 39  1  0
 39 40  2  0
 39 41  1  0
 41 42  1  0
 41 46  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
M  ISO  1  18  14
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 621.74

Molecular Weight (Monoisotopic): 621.2951

AlogP: 4.66

#Rotatable Bonds: 6

Polar Surface Area: 117.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.38

CX Basic pKa: 3.94

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.32

Np Likeness Score: -0.99

References

1. Lou Y, Lopez F, Jiang Y, Han X, Brotherton C, Billedeau R, Gabriel S, Gleason S, Goldstein DM, Hilgenkamp R, Kocer B, Orzechowski L, Tan J, Wovkulich P, Wen B, Fry D, Di Lello P, Chen L, Zhang FJ, Fretland J, Nangia A, Yang T, Owens TD..  (2017)  Mitigation of reactive metabolite formation for a series of 3-amino-2-pyridone inhibitors of Bruton's tyrosine kinase (BTK).,  27  (3): [PMID:28025004] [10.1016/j.bmcl.2016.11.092]

Source

Source(1):

• Scientific Literature