4-(((3-Methyl-5-(1H-pyrazolo[3,4-b]pyridin-4-yl)pyridin-2-yl)oxy)methyl)bicyclo[2.2.2]octan-1-amine

ID: ALA4634860

PubChem CID: 156014397

Max Phase: Preclinical

Molecular Formula: C21H25N5O

Molecular Weight: 363.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2ccnc3[nH]ncc23)cnc1OCC12CCC(N)(CC1)CC2

Standard InChI:  InChI=1S/C21H25N5O/c1-14-10-15(16-2-9-23-18-17(16)12-25-26-18)11-24-19(14)27-13-20-3-6-21(22,7-4-20)8-5-20/h2,9-12H,3-8,13,22H2,1H3,(H,23,25,26)

Standard InChI Key:  DWTASGLRYAARGP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    2.4303   -3.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650   -4.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -4.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0831   -3.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8182   -3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6420   -3.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -2.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812   -1.9039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288   -2.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -3.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3450   -4.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1693   -4.4893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550   -3.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1103   -3.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -3.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926   -2.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3800   -3.7253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7638   -2.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5888   -2.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0274   -3.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8488   -3.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2366   -2.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7968   -2.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9690   -2.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0617   -2.8762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2984   -2.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5194   -3.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  4 10  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 19 26  1  0
 22 27  1  0
 27 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4634860

   ---

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: 363.47

Molecular Weight (Monoisotopic): 363.2059

AlogP: 3.76

#Rotatable Bonds: 4

Polar Surface Area: 89.71

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: 10.94

CX LogP: 1.98

CX LogD: -0.13

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -0.56

References

1. Knoepfel T, Nimsgern P, Jacquier S, Bourrel M, Vangrevelinghe E, Glatthar R, Behnke D, Alper PB, Michellys PY, Deane J, Junt T, Zipfel G, Limonta S, Hawtin S, Andre C, Boulay T, Loetscher P, Faller M, Blank J, Feifel R, Betschart C..  (2020)  Target-Based Identification and Optimization of 5-Indazol-5-yl Pyridones as Toll-like Receptor 7 and 8 Antagonists Using a Biochemical TLR8 Antagonist Competition Assay.,  63  (15): [PMID:32786235] [10.1021/acs.jmedchem.0c00130]

2. 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