(4-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)piperazin-1-yl)(phenyl)methanone

ID: ALA4473965

PubChem CID: 2860262

Max Phase: Preclinical

Molecular Formula: C26H25Br2N3O2

Molecular Weight: 571.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccccc1)N1CCN(CC(O)Cn2c3ccc(Br)cc3c3cc(Br)ccc32)CC1

Standard InChI:  InChI=1S/C26H25Br2N3O2/c27-19-6-8-24-22(14-19)23-15-20(28)7-9-25(23)31(24)17-21(32)16-29-10-12-30(13-11-29)26(33)18-4-2-1-3-5-18/h1-9,14-15,21,32H,10-13,16-17H2

Standard InChI Key:  DFPFJDYKYMTSJK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.0132   -8.2690    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.4605   -7.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7089   -6.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1562   -6.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6594   -7.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1067   -7.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3551   -6.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6880   -5.9715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6854   -5.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3938   -4.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1063   -5.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3938   -3.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1064   -3.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1023   -2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8149   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5234   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2360   -2.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2319   -1.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5236   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5234   -0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2320    0.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9445   -0.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9403   -1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9446   -2.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5234   -3.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8150   -3.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -6.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2854   -7.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424   -7.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9385   -7.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3915   -8.2936    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.6818   -6.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2247   -6.2926    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
  2  5  2  0
  5  6  1  0
  6  7  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 18 23  1  0
 17 24  2  0
 16 25  1  0
 25 26  1  0
 13 26  1  0
  8 27  1  0
 27 28  2  0
  6 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 27 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4473965

   1-(4-Benzoylpiperazin-1-YL)-3-(3,6-dibromo-9H-carbazol-9-YL)propan-2-OL

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: 571.31

Molecular Weight (Monoisotopic): 569.0314

AlogP: 5.14

#Rotatable Bonds: 5

Polar Surface Area: 48.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.42

CX LogP: 5.17

CX LogD: 4.86

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: -1.09

References

1. Wang T, Mäser P, Picard D..  (2016)  Inhibition of Plasmodium falciparum Hsp90 Contributes to the Antimalarial Activities of Aminoalcohol-carbazoles.,  59  (13): [PMID:27312008] [10.1021/acs.jmedchem.6b00591]

Source

Source(1):

• Scientific Literature