N-(5-Bromo-1,2-dihydro-1-(4-fluorobenzyl)-4-hydroxy-2-oxopyridin-3-yl)cycloheptanecarboxamide

ID: ALA4531834

PubChem CID: 155546621

Max Phase: Preclinical

Molecular Formula: C20H22BrFN2O3

Molecular Weight: 437.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(O)c(Br)cn(Cc2ccc(F)cc2)c1=O)C1CCCCCC1

Standard InChI:  InChI=1S/C20H22BrFN2O3/c21-16-12-24(11-13-7-9-15(22)10-8-13)20(27)17(18(16)25)23-19(26)14-5-3-1-2-4-6-14/h7-10,12,14,25H,1-6,11H2,(H,23,26)

Standard InChI Key:  ZYIXJCBHLORBDA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.2426  -20.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2426  -21.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9479  -21.4575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6531  -21.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6531  -20.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9479  -19.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3602  -21.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3620  -19.8293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0685  -20.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7774  -19.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0661  -21.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7192  -19.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3201  -18.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4526  -20.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1272  -18.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2350  -20.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5323  -19.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9479  -22.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6556  -22.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6513  -23.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3582  -23.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0669  -23.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0643  -22.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3568  -22.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7751  -23.9090    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9479  -19.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5337  -19.8293    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  4  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 10 14  1  0
 13 15  1  0
 14 16  1  0
 15 17  1  0
 16 17  1  0
  3 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
  6 26  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531834

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 437.31

Molecular Weight (Monoisotopic): 436.0798

AlogP: 4.41

#Rotatable Bonds: 4

Polar Surface Area: 71.33

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -1.20

References

1. Gado F, Di Cesare Mannelli L, Lucarini E, Bertini S, Cappelli E, Digiacomo M, Stevenson LA, Macchia M, Tuccinardi T, Ghelardini C, Pertwee RG, Manera C..  (2018)  Identification of the First Synthetic Allosteric Modulator of the CB₂ Receptors and Evidence of Its Efficacy for Neuropathic Pain Relief.,  62  (1): [PMID:29990428] [10.1021/acs.jmedchem.8b00368]

Source

Source(1):

• Scientific Literature