9-(4-aminobutyl)-1-(trifluoromethyl)-9H-pyrido[3,4-b]indol-7-ol

ID: ALA2012575

PubChem CID: 54575721

Max Phase: Preclinical

Molecular Formula: C16H16F3N3O

Molecular Weight: 323.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCCn1c2cc(O)ccc2c2ccnc(C(F)(F)F)c21

Standard InChI:  InChI=1S/C16H16F3N3O/c17-16(18,19)15-14-12(5-7-21-15)11-4-3-10(23)9-13(11)22(14)8-2-1-6-20/h3-5,7,9,23H,1-2,6,8,20H2

Standard InChI Key:  ZJHOWXOGPROKKN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.7315    1.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7304    0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4448    0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4430    2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1580    1.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1582    0.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9482    0.5407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9478    1.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4332    1.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2567    1.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5959    2.0531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1055    2.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2836    2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7397    0.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0161    0.3855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2041   -0.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6532   -0.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9091   -1.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3581   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6139   -3.0377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4026   -0.1244    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.5599    0.7122    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.3219    0.0458    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
 13  8  1  0
  3  6  2  0
 10 14  1  0
  6  7  1  0
  2 15  1  0
  7  9  1  0
  7 16  1  0
  8  5  1  0
 16 17  1  0
  1  2  2  0
 17 18  1  0
  5  4  2  0
 18 19  1  0
  8  9  2  0
 19 20  1  0
  4  1  1  0
 14 21  1  0
  9 10  1  0
 14 22  1  0
  5  6  1  0
 14 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2012575

   9-(4-aminobutyl)-1-(trifluoromethyl)-2H-pyrido[3,4-b]indol-7-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: 323.32

Molecular Weight (Monoisotopic): 323.1245

AlogP: 3.65

#Rotatable Bonds: 4

Polar Surface Area: 64.07

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.31

CX Basic pKa: 10.26

CX LogP: 1.97

CX LogD: 0.41

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: -0.21

References

1. Cuny GD, Ulyanova NP, Patnaik D, Liu JF, Lin X, Auerbach K, Ray SS, Xian J, Glicksman MA, Stein RL, Higgins JM..  (2012)  Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors.,  22  (5): [PMID:22335895] [10.1016/j.bmcl.2012.01.028]

Source

Source(1):

• Scientific Literature