US9150577, 184

ID: ALA3981997

PubChem CID: 68323386

Max Phase: Preclinical

Molecular Formula: C22H17FN4O3

Molecular Weight: 404.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(-c2ccc(F)cc2)on1)c1ccc2cc3n(c2c1)CCCNC3=O

Standard InChI:  InChI=1S/C22H17FN4O3/c23-16-6-4-13(5-7-16)19-12-20(26-30-19)25-21(28)15-3-2-14-10-18-22(29)24-8-1-9-27(18)17(14)11-15/h2-7,10-12H,1,8-9H2,(H,24,29)(H,25,26,28)

Standard InChI Key:  DNWADSCQPSZJGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    2.5843  -16.1906    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630  -15.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5672  -14.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843  -13.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580  -12.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559  -12.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074  -13.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2097  -11.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421  -10.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -9.1403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0590   -8.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -7.1617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -6.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -7.6082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675   -5.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7135   -4.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -3.4619    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 C   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
    2.2896    1.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   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
    1.5767   -2.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -4.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0172   -9.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 20  1  0
 27 28  1  0
 28 18  1  0
 28 29  2  0
 29 15  1  0
 11 30  1  0
 30  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3981997

   N-[5-(4-fluorophenyl)-1,2-oxazol-3-yl]-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-8-carboxamide

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: 404.40

Molecular Weight (Monoisotopic): 404.1285

AlogP: 3.82

#Rotatable Bonds: 3

Polar Surface Area: 89.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.66

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -1.37

References

1.  (2015)  Heterocyclic compounds containing an indole core, 

2. Zarrinkar, Patrick P PP and 15 more authors.  2009-10-01  AC220 is a uniquely potent and selective inhibitor of FLT3 for the treatment of acute myeloid leukemia (AML).  [PMID:19654408]

3. Costales, Abran A and 17 more authors.  2014-03-15  2-Amino-7-substituted benzoxazole analogs as potent RSK2 inhibitors.  [PMID:24534486]

4. Narayan, Satya S and 7 more authors.  2019-01-01  ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells.  [PMID:30384048]

5. Casalvieri, Kimberly A; Matheson, Christopher J; Backos, Donald S and Reigan, Philip.  2020-03-01  Substituted pteridinones as p90 ribosomal S6 protein kinase (RSK) inhibitors: A structure-activity study.  [PMID:31982240]

Source

Source(1):

• BindingDB Database