[18F]-(+/-)-cis-4-Methylbenzyl 1-[3-fluoro-4-(pyrimidin-2-ylamino)methylpiperidin-1-yl]carboxylate

ID: ALA2036513

PubChem CID: 60143318

Max Phase: Preclinical

Molecular Formula: C19H23FN4O2

Molecular Weight: 358.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(COC(=O)N2CC[C@H](CNc3ncccn3)[C@H]([18F])C2)cc1

Standard InChI:  InChI=1S/C19H23FN4O2/c1-14-3-5-15(6-4-14)13-26-19(25)24-10-7-16(17(20)12-24)11-23-18-21-8-2-9-22-18/h2-6,8-9,16-17H,7,10-13H2,1H3,(H,21,22,23)/t16-,17-/m1/s1/i20-1

Standard InChI Key:  RECBFDWSXWAXHY-CABYTMRRSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.3572   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
  8  9  1  0
  7  8  1  0
  4  7  1  1
  3 15  1  1
 16 17  2  0
 16 18  1  0
  1 16  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 23 26  1  0
 18 19  1  0
M  ISO  1  15  18
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: 358.42

Molecular Weight (Monoisotopic): 358.1805

AlogP: 3.19

#Rotatable Bonds: 5

Polar Surface Area: 67.35

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.42

CX LogP: 2.63

CX LogD: 2.63

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.89

Np Likeness Score: -1.18

References

1. Koudih R, Gilbert G, Dhilly M, Abbas A, Barré L, Debruyne D, Sobrio F..  (2012)  Synthesis and in vitro characterization of trans- and cis-[(18)F]-4-methylbenzyl 4-[(pyrimidin-2-ylamino)methyl]-3-fluoropiperidine-1-carboxylates as new potential PET radiotracer candidates for the NR2B subtype N-methyl-D-aspartate receptor.,  53  [PMID:22554495] [10.1016/j.ejmech.2012.04.011]

Source

Source(1):

• Scientific Literature