2-(3-(4-amino-6-(1-methyl-1H-pyrazol-4-ylamino)-1,3,5-triazin-2-yl)-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one sulfate

ID: ALA4207531

PubChem CID: 121362176

Max Phase: Preclinical

Molecular Formula: C26H25FN8O6S

Molecular Weight: 498.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(Nc2nc(N)nc(-c3cccc(-n4ccc5cc(C6CC6)cc(F)c5c4=O)c3CO)n2)cn1.O=S(=O)(O)O

Standard InChI:  InChI=1S/C26H23FN8O2.H2O4S/c1-34-12-17(11-29-34)30-26-32-23(31-25(28)33-26)18-3-2-4-21(19(18)13-36)35-8-7-15-9-16(14-5-6-14)10-20(27)22(15)24(35)37;1-5(2,3)4/h2-4,7-12,14,36H,5-6,13H2,1H3,(H3,28,30,31,32,33);(H2,1,2,3,4)

Standard InChI Key:  RGIPSTHMPKGWBL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.0729  -17.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4886  -17.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9258  -11.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9246  -12.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6327  -12.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3395  -11.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5174  -11.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8107  -12.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4013  -12.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966  -13.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0974  -13.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182  -11.4194    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848  -13.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2724  -14.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9676  -13.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7677  -13.6162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1728  -12.9063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6228  -12.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9850  -12.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
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  6  7  2  0
  7  8  1  0
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  9 10  1  0
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  7 12  1  0
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 17 18  2  0
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  9 13  1  0
  8 19  1  0
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 15 22  1  0
 19 23  1  0
 12 24  1  0
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 24 29  1  0
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 31 32  1  0
 32 33  2  0
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 36 35  1  0
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 32 35  1  0
 21 38  1  0
 38 39  2  0
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 40 42  1  0
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: 498.52

Molecular Weight (Monoisotopic): 498.1928

AlogP: 3.41

#Rotatable Bonds: 6

Polar Surface Area: 136.77

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: 5.22

CX LogP: 3.83

CX LogD: 3.82

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.32

Np Likeness Score: -1.21

References

1. Kawahata W, Asami T, Kiyoi T, Irie T, Taniguchi H, Asamitsu Y, Inoue T, Miyake T, Sawa M..  (2018)  Design and Synthesis of Novel Amino-triazine Analogues as Selective Bruton's Tyrosine Kinase Inhibitors for Treatment of Rheumatoid Arthritis.,  61  (19): [PMID:30216722] [10.1021/acs.jmedchem.8b01147]

Source

Source(1):

• Scientific Literature