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

ID: ALA544286

PubChem CID: 45260628

Max Phase: Preclinical

Molecular Formula: C28H32ClF2N3O2S

Molecular Weight: 511.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NCCCCN2CC[C@@H]3C(C2)c2cc(F)ccc2N3c2ccc(F)cc2)cc1.Cl

Standard InChI:  InChI=1S/C28H31F2N3O2S.ClH/c1-20-4-11-24(12-5-20)36(34,35)31-15-2-3-16-32-17-14-28-26(19-32)25-18-22(30)8-13-27(25)33(28)23-9-6-21(29)7-10-23;/h4-13,18,26,28,31H,2-3,14-17,19H2,1H3;1H/t26?,28-;/m1./s1

Standard InChI Key:  AYGDZDJRDOWUHP-DPTRRNGNSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
    7.5335   -1.7583    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
  -11.5014    0.8095    0.0000 S   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
  -12.8028    1.5569    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
  -11.4990   -0.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4611    0.2113    0.0000 O   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
  -10.2029    1.5620    0.0000 N   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
  -14.1002    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8063    3.0569    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
  -14.1070    3.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4009    1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4043    3.0510    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
   -8.9014    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4449    3.6486    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
   -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  7  1  0
  5  7  1  0
  4  8  1  0
  6  9  1  0
  3 10  1  0
  2 11  1  0
 10 12  1  0
  5 13  2  0
  6 14  2  0
  6 15  2  0
  7 16  2  0
  6 17  1  0
  8 18  1  0
 12 18  1  0
  9 19  2  0
  9 20  1  0
 11 21  1  0
 11 22  2  0
 16 23  1  0
 13 24  1  0
 23 24  2  0
 22 26  1  0
 25 26  2  0
 21 27  2  0
 25 27  1  0
 20 28  2  0
 19 29  1  0
 28 30  1  0
 29 30  2  0
 23 31  1  0
 25 32  1  0
 12 33  1  0
 17 34  1  0
 30 35  1  0
 33 36  1  0
 34 37  1  0
 36 37  1  0
  4 38  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: 511.64

Molecular Weight (Monoisotopic): 511.2105

AlogP: 5.34

#Rotatable Bonds: 8

Polar Surface Area: 52.65

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.41

CX Basic pKa: 7.91

CX LogP: 5.31

CX LogD: 4.68

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.41

Np Likeness Score: -1.46

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