1-[[4-(6-amino-1-methyl-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluoro-phenoxy]methyl]bicyclo[2.2.2]octan-4-ol

ID: ALA4745239

PubChem CID: 162648844

Max Phase: Preclinical

Molecular Formula: C21H24FN5O2

Molecular Weight: 397.45

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H24FN5O2/c1-27-18-14(11-24-19(23)25-18)17(26-27)13-2-3-16(15(22)10-13)29-12-20-4-7-21(28,8-5-20)9-6-20/h2-3,10-11,28H,4-9,12H2,1H3,(H2,23,24,25)

Standard InChI Key:  LYETXVFKGDZVBY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   21.9761  -13.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9749  -14.7613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6871  -15.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6853  -13.5205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2600  -13.5209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4022  -13.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4070  -14.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1953  -15.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6768  -14.3359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1875  -13.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4396  -12.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4564  -15.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9019  -16.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1625  -17.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9718  -17.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5200  -16.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2607  -15.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3292  -16.8954    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.2340  -18.1361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0428  -18.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3008  -19.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7531  -19.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0123  -20.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8165  -20.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3693  -20.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1097  -19.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2946  -19.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9591  -19.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0251  -21.4327    0.0000 O   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
 21 27  1  0
 27 28  1  0
 28 24  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4745239

   ---

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: 397.45

Molecular Weight (Monoisotopic): 397.1914

AlogP: 3.22

#Rotatable Bonds: 4

Polar Surface Area: 99.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.89

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -0.84

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