3-(4-(4-(dimethylamino)phenyl)diazenyl)benzylidene)indolin-2-one

ID: ALA2206023

PubChem CID: 71459623

Max Phase: Preclinical

Molecular Formula: C23H20N4O

Molecular Weight: 368.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(/N=N/c2ccc(/C=C3\C(=O)Nc4ccccc43)cc2)cc1

Standard InChI:  InChI=1S/C23H20N4O/c1-27(2)19-13-11-18(12-14-19)26-25-17-9-7-16(8-10-17)15-21-20-5-3-4-6-22(20)24-23(21)28/h3-15H,1-2H3,(H,24,28)/b21-15-,26-25+

Standard InChI Key:  GMYSOINRJLKZRC-RTKJFNHXSA-N

Molfile:  

     RDKit          2D

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   32.8967   -3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8956   -4.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6036   -4.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6018   -3.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3105   -3.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3107   -4.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0894   -4.6915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5704   -4.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0889   -3.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3876   -4.0287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3412   -2.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1405   -2.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6837   -3.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4823   -2.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7353   -2.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1835   -1.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3869   -1.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5343   -1.9113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0822   -2.5177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8812   -2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4264   -2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2248   -2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4767   -2.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9241   -1.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1278   -1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2755   -1.8323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8241   -2.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5257   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206023

   (3Z)-3-[[4-[[4-(dimethylamino)phenyl]diazenyl]phenyl]methylidene]-1H-indol-2-one

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: 368.44

Molecular Weight (Monoisotopic): 368.1637

AlogP: 5.66

#Rotatable Bonds: 4

Polar Surface Area: 57.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.31

CX Basic pKa: 3.58

CX LogP: 5.78

CX LogD: 5.78

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.66

References

1. Amombo GM, Kramer T, Lo Monte F, Göring S, Fach M, Smith S, Kolb S, Schubenel R, Baumann K, Schmidt B..  (2012)  Modification of a promiscuous inhibitor shifts the inhibition from γ-secretase to FLT-3.,  22  (24): [PMID:23107479] [10.1016/j.bmcl.2012.10.016]

Source

Source(1):

• Scientific Literature