3-[4-[(4-amino-1-bicyclo[2.2.2]octanyl)methoxy]-3-fluoro-phenyl]-1-methyl-pyrazolo[3,4-d]pyrimidin-6-amine

ID: ALA4748638

PubChem CID: 129073171

Max Phase: Preclinical

Molecular Formula: C21H25FN6O

Molecular Weight: 396.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(-c2ccc(OCC34CCC(N)(CC3)CC4)c(F)c2)c2cnc(N)nc21

Standard InChI:  InChI=1S/C21H25FN6O/c1-28-18-14(11-25-19(23)26-18)17(27-28)13-2-3-16(15(22)10-13)29-12-20-4-7-21(24,8-5-20)9-6-20/h2-3,10-11H,4-9,12,24H2,1H3,(H2,23,25,26)

Standard InChI Key:  JGBLHVKRSBVZJG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.3791  -14.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779  -15.1616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0901  -15.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0883  -13.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6630  -13.9213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8052  -14.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8100  -15.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5983  -15.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0797  -14.7363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5905  -14.0686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8426  -13.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8594  -16.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3049  -16.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5655  -17.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3748  -17.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9230  -17.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6637  -16.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7322  -17.2957    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.6370  -18.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4458  -18.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7038  -19.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1561  -20.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4153  -20.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2195  -21.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7723  -20.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5127  -19.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4787  -21.8323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6976  -20.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3620  -20.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
 10 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 21 20  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 21 28  1  0
 28 29  1  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4748638

   ---

2. Alternative Forms:

   

   ALA4748638

   ---

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: 396.47

Molecular Weight (Monoisotopic): 396.2074

AlogP: 3.18

#Rotatable Bonds: 4

Polar Surface Area: 104.87

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.73

CX LogP: 2.63

CX LogD: -0.23

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.00

References

1. Alper PB,Deane J,Betschart C,Buffet D,Collignon Zipfel G,Gordon P,Hampton J,Hawtin S,Ibanez M,Jiang T,Junt T,Knoepfel T,Liu B,Maginnis J,McKeever U,Michellys PY,Mutnick D,Nayak B,Niwa S,Richmond W,Rush JS,Syka P,Zhang Y,Zhu X.  (2020)  Discovery of potent, orally bioavailable in vivo efficacious antagonists of the TLR7/8 pathway.,  30  (17): [PMID:32738975] [10.1016/j.bmcl.2020.127366]

Source

Source(1):

• Scientific Literature