4-Benzyl-1-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-propyl]-piperidine

ID: ALA147201

PubChem CID: 12045496

Max Phase: Preclinical

Molecular Formula: C18H25N3S2

Molecular Weight: 347.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc(SCCCN2CCC(Cc3ccccc3)CC2)s1

Standard InChI:  InChI=1S/C18H25N3S2/c1-15-19-20-18(23-15)22-13-5-10-21-11-8-17(9-12-21)14-16-6-3-2-4-7-16/h2-4,6-7,17H,5,8-14H2,1H3

Standard InChI Key:  AKHPGLXRXQHYOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.2875   -6.5792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2000   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9542   -5.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5042   -6.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -6.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -5.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -5.3417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -5.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4292   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  5  2  0
  5  1  1  0
  6 13  1  0
  7  2  1  0
  8  6  1  0
  9  6  1  0
 10 11  1  0
 11 14  1  0
 12 10  1  0
 13 16  1  0
 14  9  1  0
 15  8  1  0
 16 18  1  0
 17  5  1  0
 18  7  1  0
 19 12  2  0
 20 12  1  0
 21 19  1  0
 22 20  2  0
 23 22  1  0
  4  3  1  0
 11 15  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA147201

   2-(3-(4-Benzylpiperidin-1-yl)propylthio)-5-methyl-1,3,4-thiadiazole

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: 347.55

Molecular Weight (Monoisotopic): 347.1490

AlogP: 4.28

#Rotatable Bonds: 7

Polar Surface Area: 29.02

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 3.87

CX LogD: 2.47

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: -1.80

References

1. Gregory TF, Wright JL, Wise LD, Meltzer LT, Serpa KA, Konkoy CS, Whittemore ER, Woodward RM..  (2000)  Parallel synthesis of a series of subtype-selective NMDA receptor antagonists.,  10  (6): [PMID:10741546] [10.1016/s0960-894x(00)00035-4]

2. Mony L, Triballeau N, Paoletti P, Acher FC, Bertrand HO..  (2010)  Identification of a novel NR2B-selective NMDA receptor antagonist using a virtual screening approach.,  20  (18): [PMID:20692832] [10.1016/j.bmcl.2010.07.043]

Source

Source(1):

• Scientific Literature