3-[7-(2-Hydroxy-2-methylpropyl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile

ID: ALA4536380

PubChem CID: 54766428

Max Phase: Preclinical

Molecular Formula: C22H23N7O3

Molecular Weight: 433.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(O)Cn1c(=O)n(C2CCOCC2)c2nc(-c3cnc4ccc(C#N)cn34)ncc21

Standard InChI:  InChI=1S/C22H23N7O3/c1-22(2,31)13-28-17-11-25-19(16-10-24-18-4-3-14(9-23)12-27(16)18)26-20(17)29(21(28)30)15-5-7-32-8-6-15/h3-4,10-12,15,31H,5-8,13H2,1-2H3

Standard InChI Key:  GVFYFXFHOOSHAM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    7.4331  -28.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1918  -26.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1907  -27.1223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987  -27.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970  -25.8939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056  -26.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6058  -27.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3845  -27.3706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8655  -26.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3841  -26.0460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885  -25.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950  -25.6201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421  -26.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035  -24.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060  -25.0849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9537  -24.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6396  -25.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4402  -25.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3485  -23.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0920  -24.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1486  -23.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6929  -24.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6827  -26.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6372  -28.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9800  -27.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6856  -29.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2214  -28.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2537  -23.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8029  -22.4857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
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  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
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  2 11  1  0
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 14 19  1  0
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 16 17  2  0
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 20 21  1  0
 20 23  1  0
 21 25  1  0
 22 23  1  0
 10 20  1  0
 22 24  1  0
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  9 26  2  0
  8 27  1  0
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  1 28  1  0
  1 29  1  0
  1 30  1  0
 31 32  3  0
 17 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536380

   3-[7-(2-Hydroxy-2-methylpropyl)-9-(oxan-4-yl)-8-oxopurin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile

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: 433.47

Molecular Weight (Monoisotopic): 433.1862

AlogP: 1.90

#Rotatable Bonds: 4

Polar Surface Area: 123.26

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.53

CX LogP: 1.29

CX LogD: 1.29

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.24

References

1. Bach J, Eastwood P, González J, Gómez E, Alonso JA, Fonquerna S, Lozoya E, Orellana A, Maldonado M, Calaf E, Albertí J, Pérez J, Andrés A, Prats N, Carreño C, Calama E, De Alba J, Calbet M, Miralpeix M, Ramis I..  (2019)  Identification of 2-Imidazopyridine and 2-Aminopyridone Purinones as Potent Pan-Janus Kinase (JAK) Inhibitors for the Inhaled Treatment of Respiratory Diseases.,  62  (20): [PMID:31609613] [10.1021/acs.jmedchem.9b00533]

Source

Source(1):

• Scientific Literature