(E)-9-Ethyl-6,6-dimethyl-8-(3-morpholinoprop-1-en-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

ID: ALA3747585

PubChem CID: 127038283

Max Phase: Preclinical

Molecular Formula: C28H29N3O2

Molecular Weight: 439.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc2c(cc1/C=C/CN1CCOCC1)C(C)(C)c1[nH]c3cc(C#N)ccc3c1C2=O

Standard InChI:  InChI=1S/C28H29N3O2/c1-4-19-15-22-23(16-20(19)6-5-9-31-10-12-33-13-11-31)28(2,3)27-25(26(22)32)21-8-7-18(17-29)14-24(21)30-27/h5-8,14-16,30H,4,9-13H2,1-3H3/b6-5+

Standard InChI Key:  KNORADHWAQAYMG-AATRIKPKSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    0.0000   -0.3300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -0.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    1.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    1.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2800    1.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5200    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7800    1.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7800    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2800    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500    2.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600    1.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -0.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    3.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5712   -0.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649   -0.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6520    2.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6406    3.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -0.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194   -0.9505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6665   -0.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6812   -1.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9878   -2.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024   -4.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3072   -4.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3188   -6.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0256   -7.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7208   -6.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7092   -4.8390    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  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  1 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  4 17  2  0
  5 14  2  0
  6 18  2  0
  3 19  1  0
  3 20  1  0
 21 22  1  0
 15 21  1  0
 23 24  3  0
 11 23  1  0
 16 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3747585

   ---

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: 439.56

Molecular Weight (Monoisotopic): 439.2260

AlogP: 4.82

#Rotatable Bonds: 4

Polar Surface Area: 69.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.17

CX Basic pKa: 5.61

CX LogP: 5.30

CX LogD: 5.30

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.63

Np Likeness Score: -0.06

References

1. Hatcher JM, Bahcall M, Choi HG, Gao Y, Sim T, George R, Jänne PA, Gray NS..  (2015)  Discovery of Inhibitors That Overcome the G1202R Anaplastic Lymphoma Kinase Resistance Mutation.,  58  (23): [PMID:26568289] [10.1021/acs.jmedchem.5b01136]

Source

Source(1):

• Scientific Literature