(R)-2-(5-Chloro-2-oxo-1,2-dihydropyridin-3-ylamino)-9-(8-fluorochroman-4-yl)-7H-purin-8(9H)-one

ID: ALA4482927

PubChem CID: 71061323

Max Phase: Preclinical

Molecular Formula: C19H14ClFN6O3

Molecular Weight: 428.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]cc(Cl)cc1Nc1ncc2[nH]c(=O)n([C@@H]3CCOc4c(F)cccc43)c2n1

Standard InChI:  InChI=1S/C19H14ClFN6O3/c20-9-6-12(17(28)22-7-9)24-18-23-8-13-16(26-18)27(19(29)25-13)14-4-5-30-15-10(14)2-1-3-11(15)21/h1-3,6-8,14H,4-5H2,(H,22,28)(H,25,29)(H,23,24,26)/t14-/m1/s1

Standard InChI Key:  HVJIWBVMMZRJNS-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

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   23.6216  -24.6524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3369  -25.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3351  -23.4112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0512  -23.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0514  -24.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8382  -24.9032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3242  -24.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8378  -23.5649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499  -24.2335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9075  -23.4116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9073  -22.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6248  -22.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6249  -21.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9092  -20.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1918  -21.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1952  -22.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4816  -22.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0915  -22.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6063  -21.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7974  -21.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5382  -22.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1561  -21.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8996  -22.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4466  -23.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2502  -23.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5038  -22.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9551  -21.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2095  -20.8773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.3401  -20.9376    0.0000 Cl  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  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  1 11  1  0
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 15 16  1  0
 16 17  1  0
 17 12  1  0
 17 18  2  0
 19 24  1  0
 19 22  1  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 19  9  1  6
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
 14 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4482927

   2-[(5-chloro-2-oxo-1H-pyridin-3-yl)amino]-9-[(4R)-8-fluoro-3,4-dihydro-2H-chromen-4-yl]-7H-purin-8-one

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: 428.81

Molecular Weight (Monoisotopic): 428.0800

AlogP: 2.72

#Rotatable Bonds: 3

Polar Surface Area: 117.69

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.68

CX Basic pKa: 1.89

CX LogP: 1.94

CX LogD: 1.94

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -1.32

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