8-Fluoro-5-(4-fluoro-phenyl)-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole hydrochloride

ID: ALA539257

PubChem CID: 45264452

Max Phase: Preclinical

Molecular Formula: C18H19ClF2N2

Molecular Weight: 300.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC2C(C1)c1cc(F)ccc1N2c1ccc(F)cc1.Cl

Standard InChI:  InChI=1S/C18H18F2N2.ClH/c1-21-9-8-18-16(11-21)15-10-13(20)4-7-17(15)22(18)14-5-2-12(19)3-6-14;/h2-7,10,16,18H,8-9,11H2,1H3;1H

Standard InChI Key:  GQJPBGNXQQATRW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.5335   -2.8699    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006    0.8244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959   -3.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021   -3.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -5.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080   -5.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -5.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737    1.4291    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0167   -7.0197    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7428    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  4  1  0
  2  5  1  0
  3  6  1  0
  5  6  2  0
  4  7  1  0
  3  8  1  0
  2  9  1  0
  8 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
 10 13  1  0
  9 14  2  0
  9 15  1  0
 12 16  2  0
 11 17  2  0
 16 17  1  0
 15 19  2  0
 18 19  1  0
 14 20  1  0
 18 20  2  0
 16 21  1  0
 18 22  1  0
 10 23  1  0
M  END

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: 300.35

Molecular Weight (Monoisotopic): 300.1438

AlogP: 3.90

#Rotatable Bonds: 1

Polar Surface Area: 6.48

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.87

CX LogP: 3.59

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.99

References

1. Sarges R, Howard HR, Donahue KM, Welch WM, Dominy BW, Weissman A, Koe BK, Bordner J..  (1986)  Neuroleptic activity of chiral trans-hexahydro-gamma-carbolines.,  29  (1): [PMID:3941416] [10.1021/jm00151a002]

Source

Source(1):

• Scientific Literature