US9150577, 20

ID: ALA3974341

PubChem CID: 89523841

Max Phase: Preclinical

Molecular Formula: C20H18N6O2

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ncc2cc(NC(=O)c3ccc4cc5n(c4c3)CCCNC5=O)cnc21

Standard InChI:  InChI=1S/C20H18N6O2/c1-25-18-14(10-23-25)7-15(11-22-18)24-19(27)13-4-3-12-8-17-20(28)21-5-2-6-26(17)16(12)9-13/h3-4,7-11H,2,5-6H2,1H3,(H,21,28)(H,24,27)

Standard InChI Key:  GCLXDYUBPVLGMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -0.8134  -13.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662  -12.8580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494  -12.6344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951  -11.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643  -10.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869   -9.0126    0.0000 C   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
    1.1276   -9.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502  -11.1181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958  -11.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 16  1  0
 23 24  1  0
 24 14  1  0
 24 25  2  0
 25 11  1  0
  7 26  2  0
 26 27  1  0
 27 28  2  0
 28  2  1  0
 28  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3974341

   N-(1-methylpyrazolo[3,4-b]pyridin-5-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: 374.40

Molecular Weight (Monoisotopic): 374.1491

AlogP: 2.31

#Rotatable Bonds: 2

Polar Surface Area: 93.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.26

CX LogP: 0.87

CX LogD: 0.87

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -1.52

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