(2-(4-Fluoro-1H-indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

ID: ALA4560897

PubChem CID: 155558474

Max Phase: Preclinical

Molecular Formula: C21H18FN3O4

Molecular Weight: 395.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)c2c[nH]c(-c3c[nH]c4cccc(F)c34)n2)cc(OC)c1OC

Standard InChI:  InChI=1S/C21H18FN3O4/c1-27-16-7-11(8-17(28-2)20(16)29-3)19(26)15-10-24-21(25-15)12-9-23-14-6-4-5-13(22)18(12)14/h4-10,23H,1-3H3,(H,24,25)

Standard InChI Key:  QCHSHTKZUYZPQH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   24.6865   -8.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3946   -8.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3928   -7.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1014   -7.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1062   -8.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8862   -8.5915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3636   -7.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8785   -7.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.8996   -6.2317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8948   -5.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1161   -5.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6398   -5.8305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7032   -4.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1109   -3.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8860   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9275   -3.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3352   -3.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9257   -2.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1043   -2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7003   -3.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3326   -1.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1524   -3.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6924   -1.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1498   -1.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5615   -3.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0977   -0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3903   -6.3020    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0
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 25 28  1  0
  4 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560897

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 395.39

Molecular Weight (Monoisotopic): 395.1281

AlogP: 3.95

#Rotatable Bonds: 6

Polar Surface Area: 89.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.82

CX Basic pKa: 3.86

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -0.29

References

1. Wang Q, Arnst KE, Wang Y, Kumar G, Ma D, White SW, Miller DD, Li W, Li W..  (2019)  Structure-Guided Design, Synthesis, and Biological Evaluation of (2-(1H-Indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) Methanone (ABI-231) Analogues Targeting the Colchicine Binding Site in Tubulin.,  62  (14): [PMID:31251599] [10.1021/acs.jmedchem.9b00706]

Source

Source(1):

• Scientific Literature