2,6-Dimethyl-N-[3-[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-1H-indol-7-yl]pyridine-3-carboxamide

ID: ALA4536860

PubChem CID: 155548345

Max Phase: Preclinical

Molecular Formula: C25H24N8O

Molecular Weight: 452.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)Nc2cccc3c(-c4nc(Nc5cnn(C)c5)ncc4C)c[nH]c23)c(C)n1

Standard InChI:  InChI=1S/C25H24N8O/c1-14-10-27-25(30-17-11-28-33(4)13-17)32-22(14)20-12-26-23-19(20)6-5-7-21(23)31-24(34)18-9-8-15(2)29-16(18)3/h5-13,26H,1-4H3,(H,31,34)(H,27,30,32)

Standard InChI Key:  ZWZPVJXSWZWJLP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.8367   -8.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8356   -9.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5478  -10.1226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2616   -9.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2587   -8.8864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5460   -8.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9740  -10.1207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6811   -9.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5377   -7.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1211   -6.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8711   -7.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1248   -8.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9425   -6.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1974   -7.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9978   -7.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5441   -6.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2886   -5.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4888   -5.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4264  -10.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9722   -9.4287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5625   -8.7216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7635   -8.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8936   -7.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2340   -5.0074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7791   -4.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5243   -3.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5789   -4.5661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0721   -3.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8178   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0172   -2.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4714   -2.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7285   -3.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1866   -4.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7614   -1.3028    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
  4  7  1  0
  7  8  1  0
  9 14  1  0
 13 10  1  0
 10 11  1  0
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  6  9  1  0
  1 12  1  0
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 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22  8  2  0
 21 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 26  1  0
 32 33  1  0
 30 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536860

   ---

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: 452.52

Molecular Weight (Monoisotopic): 452.2073

AlogP: 4.67

#Rotatable Bonds: 5

Polar Surface Area: 113.41

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.24

CX Basic pKa: 5.24

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -1.64

References

1. Su Q, Banks E, Bebernitz G, Bell K, Borenstein CF, Chen H, Chuaqui CE, Deng N, Ferguson AD, Kawatkar S, Grimster NP, Ruston L, Lyne PD, Read JA, Peng X, Pei X, Fawell S, Tang Z, Throner S, Vasbinder MM, Wang H, Winter-Holt J, Woessner R, Wu A, Yang W, Zinda M, Kettle JG..  (2020)  Discovery of (2R)-N-[3-[2-[(3-Methoxy-1-methyl-pyrazol-4-yl)amino]pyrimidin-4-yl]-1H-indol-7-yl]-2-(4-methylpiperazin-1-yl)propenamide (AZD4205) as a Potent and Selective Janus Kinase 1 Inhibitor.,  63  (9): [PMID:32297743] [10.1021/acs.jmedchem.9b01392]

Source

Source(1):

• Scientific Literature