9-(2-hydroxy-3-(4-methylpiperazin-1-yl)propyl)-9H-carbazole-3,6-dicarbonitrile

ID: ALA5278886

Max Phase: Preclinical

Molecular Formula: C22H23N5O

Molecular Weight: 373.46

Names and Identifiers

Canonical SMILES:  CN1CCN(CC(O)Cn2c3ccc(C#N)cc3c3cc(C#N)ccc32)CC1

Standard InChI:  InChI=1S/C22H23N5O/c1-25-6-8-26(9-7-25)14-18(28)15-27-21-4-2-16(12-23)10-19(21)20-11-17(13-24)3-5-22(20)27/h2-5,10-11,18,28H,6-9,14-15H2,1H3

Standard InChI Key:  FJIYHDSBZHRWFS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.6880   -0.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928    0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416    0.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642    0.5847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    1.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    1.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    2.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    1.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    1.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    0.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6196   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -1.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -2.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6414   -2.7029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2193    2.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7905    2.7029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7001    0.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -0.3030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585   -0.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082   -0.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508   -1.5321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437   -1.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940   -1.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -2.0238    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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  4  1  0
 16 11  2  0
 13 17  1  0
 17 18  3  0
  8 19  1  0
 19 20  3  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278886

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 373.46

Molecular Weight (Monoisotopic): 373.1903

AlogP: 2.15

#Rotatable Bonds: 4

Polar Surface Area: 79.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.28

CX LogP: 2.26

CX LogD: 1.33

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -1.14

References

1. Clausen JD, Kjellerup L, Cohrt KO, Hansen JB, Dalby-Brown W, Winther AL..  (2017)  Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives.,  27  (19): [PMID:28893470] [10.1016/j.bmcl.2017.08.067]

Source

Source(1):

• Scientific Literature