(+/-)-(4-((2S,3S)-2-(Benzo[d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-azetidin-1-yl)piperidin-1-yl)(1H-1,2,4-triazol-1-yl)methanone

ID: ALA3787453

PubChem CID: 127033069

Max Phase: Preclinical

Molecular Formula: C24H24FN5O3

Molecular Weight: 449.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCC(N2C[C@H](c3ccc(F)cc3)[C@H]2c2ccc3c(c2)OCO3)CC1)n1cncn1

Standard InChI:  InChI=1S/C24H24FN5O3/c25-18-4-1-16(2-5-18)20-12-29(23(20)17-3-6-21-22(11-17)33-15-32-21)19-7-9-28(10-8-19)24(31)30-14-26-13-27-30/h1-6,11,13-14,19-20,23H,7-10,12,15H2/t20-,23-/m1/s1

Standard InChI Key:  IWSLFABPEBZJJD-NFBKMPQASA-N

Molfile:  

     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
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   -5.4118    2.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0201    1.0775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004    4.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374    4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    5.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    7.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    6.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870    5.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7510   -0.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2474   -1.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2167   -2.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6928   -2.5108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1995   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2301    0.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    8.1659    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6650   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2616   -4.7843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1415   -3.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2072   -4.4221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5260   -3.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2538   -2.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7668   -2.0354    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  1  1  0
  5  6  2  0
  6 23  1  0
 22  7  1  0
  7  8  2  0
  8  5  1  0
  4  5  1  1
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  1  9  1  6
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  3 15  1  0
 12 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 18 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3787453

   ---

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: 449.49

Molecular Weight (Monoisotopic): 449.1863

AlogP: 3.42

#Rotatable Bonds: 3

Polar Surface Area: 72.72

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.06

CX LogP: 2.10

CX LogD: 1.36

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.61

Np Likeness Score: -0.80

References

1. Brindisi M, Maramai S, Gemma S, Brogi S, Grillo A, Di Cesare Mannelli L, Gabellieri E, Lamponi S, Saponara S, Gorelli B, Tedesco D, Bonfiglio T, Landry C, Jung KM, Armirotti A, Luongo L, Ligresti A, Piscitelli F, Bertucci C, Dehouck MP, Campiani G, Maione S, Ghelardini C, Pittaluga A, Piomelli D, Di Marzo V, Butini S..  (2016)  Development and Pharmacological Characterization of Selective Blockers of 2-Arachidonoyl Glycerol Degradation with Efficacy in Rodent Models of Multiple Sclerosis and Pain.,  59  (6): [PMID:26888301] [10.1021/acs.jmedchem.5b01812]

Source

Source(1):

• Scientific Literature