N-{7-[8-Fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-heptyl}-acetamide hydrochloride

ID: ALA556616

PubChem CID: 45264586

Max Phase: Preclinical

Molecular Formula: C26H34ClF2N3O

Molecular Weight: 441.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NCCCCCCCN1CC[C@@H]2C(C1)c1cc(F)ccc1N2c1ccc(F)cc1.Cl

Standard InChI:  InChI=1S/C26H33F2N3O.ClH/c1-19(32)29-14-5-3-2-4-6-15-30-16-13-26-24(18-30)23-17-21(28)9-12-25(23)31(26)22-10-7-20(27)8-11-22;/h7-12,17,24,26H,2-6,13-16,18H2,1H3,(H,29,32);1H/t24?,26-;/m1./s1

Standard InChI Key:  SDKDWNPQJDFRBF-PICYYWTMSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    7.5335   -2.1339    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
  -15.4028    1.5518    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
  -16.4411    0.9501    0.0000 O   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
  -14.1014    0.8044    0.0000 N   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
   -5.0029    1.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4052    2.7518    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
   -6.3014    0.8196    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
   -7.6029    1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2029    1.5620    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
   -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  8  1  0
  2  9  1  0
  8 10  1  0
  5 11  2  0
  6 12  2  0
  7 14  1  0
 10 14  1  0
 13 15  2  0
  9 16  2  0
  9 17  1  0
 12 18  1  0
 13 19  1  0
 11 20  1  0
 18 20  2  0
 17 22  2  0
 21 22  1  0
 16 23  1  0
 21 23  2  0
 18 24  1  0
 21 25  1  0
 10 26  1  0
 13 27  1  0
 19 28  1  0
 26 29  1  0
 28 30  1  0
 29 31  1  0
 30 32  1  0
 31 33  1  0
 32 33  1  0
  4 34  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: 441.57

Molecular Weight (Monoisotopic): 441.2592

AlogP: 5.36

#Rotatable Bonds: 9

Polar Surface Area: 35.58

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.64

CX LogP: 4.52

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: -1.06

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