US9034866, 96

ID: ALA3692450

PubChem CID: 86693188

Max Phase: Preclinical

Molecular Formula: C22H21N5O5

Molecular Weight: 435.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1c(C(N)=O)nc2n1CCOc1ccc(C#C[C@@](C)(O)c3cc(C)on3)cc1-2

Standard InChI:  InChI=1S/C22H21N5O5/c1-12-10-16(26-32-12)22(2,30)7-6-13-4-5-15-14(11-13)20-25-17(19(23)28)18(21(29)24-3)27(20)8-9-31-15/h4-5,10-11,30H,8-9H2,1-3H3,(H2,23,28)(H,24,29)/t22-/m1/s1

Standard InChI Key:  HYLUNVLDXOSFLG-JOCHJYFZSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  1  0  0  0  0  0999 V2000
    1.5890   -6.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082   -5.3712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -4.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302   -4.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5767   -2.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0899   -0.9120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913    1.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278    4.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1116    3.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193    4.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9593    5.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1993    5.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1093    7.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2894    4.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5519    5.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8010    3.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2875    3.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8568    2.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9375    4.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8526    6.0269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959   -3.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3124   -2.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -4.5291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  5  1  0
 18  8  1  0
 11 19  1  0
 19 20  3  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 24  2  0
  6 30  1  0
 30 31  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3692450

   10-[(3R)-3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-ynyl]-N3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 435.44

Molecular Weight (Monoisotopic): 435.1543

AlogP: 0.96

#Rotatable Bonds: 3

Polar Surface Area: 145.50

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.67

CX Basic pKa: 0.86

CX LogP: 0.73

CX LogD: 0.73

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.08

References

1.  (2015)  Tricyclic compounds and methods of use therefor, 

2. Castanedo GM, Blaquiere N, Beresini M, Bravo B, Brightbill H, Chen J, Cui HF, Eigenbrot C, Everett C, Feng J, Godemann R, Gogol E, Hymowitz S, Johnson A, Kayagaki N, Kohli PB, Knüppel K, Kraemer J, Krüger S, Loke P, McEwan P, Montalbetti C, Roberts DA, Smith M, Steinbacher S, Sujatha-Bhaskar S, Takahashi R, Wang X, Wu LC, Zhang Y, Staben ST..  (2017)  Structure-Based Design of Tricyclic NF-κB Inducing Kinase (NIK) Inhibitors That Have High Selectivity over Phosphoinositide-3-kinase (PI3K).,  60  (2): [PMID:28005357] [10.1021/acs.jmedchem.6b01363]

3. Song J,Zhu Y,Zu W,Duan C,Xu J,Jiang F,Wang X,Li S,Liu C,Gao Q,Li H,Zhang Y,Tang W,Lu T,Chen Y.  (2021)  The discovery of quinoline derivatives, as NF-κB inducing kinase (NIK) inhibitors with anti-inflammatory effects in vitro, low toxicities against T cell growth.,  29  [PMID:33199201] [10.1016/j.bmc.2020.115856]

Source

Source(2):

• Scientific Literature
• BindingDB Database