1-(3-(9H-carbazol-9-yl)propyl)-4-(4-methoxyphenyl)piperidin-4-ol

ID: ALA1164505

PubChem CID: 5311322

Max Phase: Preclinical

Molecular Formula: C27H30N2O2

Molecular Weight: 414.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(O)CCN(CCCn3c4ccccc4c4ccccc43)CC2)cc1

Standard InChI:  InChI=1S/C27H30N2O2/c1-31-22-13-11-21(12-14-22)27(30)15-19-28(20-16-27)17-6-18-29-25-9-4-2-7-23(25)24-8-3-5-10-26(24)29/h2-5,7-14,30H,6,15-20H2,1H3

Standard InChI Key:  XZPJYOWZGPSDDJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   11.7000   -8.9719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7029   -9.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9888  -10.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9917  -11.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2776  -11.4539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9697  -11.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5201  -11.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2664  -10.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624  -10.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9128  -10.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1695  -11.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1941  -12.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3899  -12.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1366  -13.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6907  -13.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4973  -13.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7426  -12.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4123   -8.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4113   -7.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7002   -7.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9843   -7.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9836   -8.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1108   -6.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4095   -6.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1303   -7.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8432   -6.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8358   -6.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1096   -5.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3996   -6.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5469   -5.6470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5380   -4.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  6  7  2  0
 15 16  1  0
  3  4  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  7  8  1  0
  8  9  2  0
  4  5  1  0
  9 10  1  0
  1 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  5  7  1  0
 20 23  1  0
 10 11  2  0
 20 24  1  0
 11  6  1  0
 24 25  2  0
  6 13  1  0
 25 26  1  0
 12  5  1  0
 26 27  2  0
 12 13  2  0
 27 28  1  0
  2  3  1  0
 28 29  2  0
 29 24  1  0
 13 14  1  0
 27 30  1  0
  1  2  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1164505

   1-(3-Carbazol-9-ylpropyl)-4-(4-methoxyphenyl)piperidin-4-ol

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: 414.55

Molecular Weight (Monoisotopic): 414.2307

AlogP: 5.18

#Rotatable Bonds: 6

Polar Surface Area: 37.63

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.64

CX LogP: 4.20

CX LogD: 1.99

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -0.45

References

1. Faust MR, Höfner G, Pabel J, Wanner KT..  (2010)  Azetidine derivatives as novel gamma-aminobutyric acid uptake inhibitors: synthesis, biological evaluation, and structure-activity relationship.,  45  (6): [PMID:20219271] [10.1016/j.ejmech.2010.02.029]

2. Hack S, Wörlein B, Höfner G, Pabel J, Wanner KT..  (2011)  Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.,  46  (5): [PMID:21353350] [10.1016/j.ejmech.2011.01.042]

Source

Source(1):

• Scientific Literature