N-{4-[8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-butyl}-benzamide hydrochloride

ID: ALA544994

PubChem CID: 45260640

Max Phase: Preclinical

Molecular Formula: C28H30ClF2N3O

Molecular Weight: 461.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(NCCCCN1CC[C@@H]2C(C1)c1cc(F)ccc1N2c1ccc(F)cc1)c1ccccc1

Standard InChI:  InChI=1S/C28H29F2N3O.ClH/c29-21-8-11-23(12-9-21)33-26-13-10-22(30)18-24(26)25-19-32(17-14-27(25)33)16-5-4-15-31-28(34)20-6-2-1-3-7-20;/h1-3,6-13,18,25,27H,4-5,14-17,19H2,(H,31,34);1H/t25?,27-;/m1./s1

Standard InChI Key:  FZWSQLMPZDGOHW-IMFLJNHTSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    7.5335   -1.7569    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
  -11.5014    0.8095    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
  -11.4990   -0.3905    0.0000 O   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
  -12.8028    1.5569    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
  -10.2029    1.5620    0.0000 N   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
    1.2900   -5.0749    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
    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
   -5.0029    1.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1018    0.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8033    3.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9014    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014    0.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6029    1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1025    3.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4010    1.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4014    3.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2338   -1.6045    0.0000 H   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  1  0
  4  7  1  0
  3  9  1  0
  2 10  1  0
  9 11  1  0
  5 12  2  0
  6 13  2  0
  8 14  2  0
  7 15  1  0
 11 15  1  0
  8 16  1  0
 10 17  1  0
 10 18  2  0
  8 19  1  0
 13 20  1  0
 12 21  1  0
 20 21  2  0
 17 23  2  0
 22 23  1  0
 18 24  1  0
 22 24  2  0
 20 25  1  0
 22 26  1  0
 11 27  1  0
 16 28  2  0
 16 29  1  0
 19 30  1  0
 27 31  1  0
 30 32  1  0
 31 32  1  0
 29 33  2  0
 28 34  1  0
 33 35  1  0
 34 35  2  0
  4 36  1  1
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: 461.56

Molecular Weight (Monoisotopic): 461.2279

AlogP: 5.48

#Rotatable Bonds: 7

Polar Surface Area: 35.58

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.34

CX LogP: 5.04

CX LogD: 4.06

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.47

Np Likeness Score: -1.23

References

1. Welch WM, Harbert CA, Sarges R, Weissman A, Koe BK..  (1986)  Neuroleptics from the 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole series. 3. Carboxamidoalkyl derivatives.,  29  (10): [PMID:2876105] [10.1021/jm00160a053]

Source

Source(1):

• Scientific Literature