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

ID: ALA556410

PubChem CID: 45264528

Max Phase: Preclinical

Molecular Formula: C24H30ClF2N3O2

Molecular Weight: 429.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H29F2N3O2.ClH/c1-2-31-24(30)27-12-3-4-13-28-14-11-23-21(16-28)20-15-18(26)7-10-22(20)29(23)19-8-5-17(25)6-9-19;/h5-10,15,21,23H,2-4,11-14,16H2,1H3,(H,27,30);1H/t21?,23-;/m1./s1

Standard InChI Key:  VIDWERLJWUFKAI-PZFASQSNSA-N

Molfile:  

     RDKit          2D

 33 35  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
  -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
  -10.2029    1.5620    0.0000 N   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
  -12.8028    1.5569    0.0000 O   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
   -8.9014    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1014    0.8044    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
  -15.1420    1.4020    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
 13 19  1  0
 12 20  1  0
 19 20  2  0
  8 21  1  0
 17 23  2  0
 22 23  1  0
 18 24  1  0
 22 24  2  0
 19 25  1  0
 22 26  1  0
 11 27  1  0
 16 28  1  0
 21 29  1  0
 27 30  1  0
 28 31  1  0
 30 31  1  0
 29 32  1  0
  4 33  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: 429.51

Molecular Weight (Monoisotopic): 429.2228

AlogP: 4.80

#Rotatable Bonds: 7

Polar Surface Area: 44.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.34

CX LogP: 4.16

CX LogD: 3.18

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: -1.24

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