5-chloro-3-((9-methyl-9H-carbazol-3-yl)methylene)indolin-2-one

ID: ALA2206026

PubChem CID: 71457712

Max Phase: Preclinical

Molecular Formula: C22H15ClN2O

Molecular Weight: 358.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c2ccccc2c2cc(/C=C3\C(=O)Nc4ccc(Cl)cc43)ccc21

Standard InChI:  InChI=1S/C22H15ClN2O/c1-25-20-5-3-2-4-15(20)17-10-13(6-9-21(17)25)11-18-16-12-14(23)7-8-19(16)24-22(18)26/h2-12H,1H3,(H,24,26)/b18-11-

Standard InChI Key:  VFNSOYZWZXNWDN-WQRHYEAKSA-N

Molfile:  

     RDKit          2D

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   19.8494   -9.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5575  -10.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5557   -8.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2643   -8.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2645   -9.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0432   -9.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5242   -9.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0428   -8.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3414   -9.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2950   -7.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0943   -7.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6376   -8.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1373   -6.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3408   -6.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1427   -8.4775    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.6891   -7.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4375   -8.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5039   -7.3446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7559   -8.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0985   -8.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1826   -9.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9235   -9.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5812   -9.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4937   -8.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9841   -6.6834    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 18  1  0
 17 14  1  0
 14 15  2  0
 15 12  1  0
  1 16  1  0
 17 18  2  0
 18 21  1  0
 20 19  1  0
 19 17  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
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206026

   (3Z)-5-chloro-3-[(9-methylcarbazol-3-yl)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: 358.83

Molecular Weight (Monoisotopic): 358.0873

AlogP: 5.48

#Rotatable Bonds: 1

Polar Surface Area: 34.03

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.29

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 5.21

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -0.60

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