1-{4-[3-(6-Methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}-2-phenylethanone

ID: ALA4525950

PubChem CID: 87551058

Max Phase: Preclinical

Molecular Formula: C22H22N2O

Molecular Weight: 330.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(C#CC=C2CCN(C(=O)Cc3ccccc3)CC2)n1

Standard InChI:  InChI=1S/C22H22N2O/c1-18-7-5-11-21(23-18)12-6-10-19-13-15-24(16-14-19)22(25)17-20-8-3-2-4-9-20/h2-5,7-11H,13-17H2,1H3

Standard InChI Key:  RLOLKWLPQCITPX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   28.2483  -19.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9564  -20.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6660  -19.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6632  -19.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9546  -18.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9562  -21.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3694  -18.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0739  -18.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7782  -17.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4893  -18.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4899  -19.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1970  -19.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9037  -19.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8988  -18.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1872  -17.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6132  -19.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6170  -20.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3191  -19.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0287  -19.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0276  -20.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7363  -20.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4431  -20.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4367  -19.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7274  -19.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  5  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
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 15 16  1  0
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 17 18  2  0
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 19 20  1  0
 20 21  2  0
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 23 24  1  0
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 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525950

   2-Methyl-6-{3-[1-(phenylacetyl)piperidin-4-ylidene]prop-1-ynyl}pyridine

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: 330.43

Molecular Weight (Monoisotopic): 330.1732

AlogP: 3.53

#Rotatable Bonds: 2

Polar Surface Area: 33.20

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.19

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.78

References

1. Graziani D, Caligari S, Callegari E, De Toma C, Longhi M, Frigerio F, Dilernia R, Menegon S, Pinzi L, Pirona L, Tazzari V, Valsecchi AE, Vistoli G, Rastelli G, Riva C..  (2019)  Evaluation of Amides, Carbamates, Sulfonamides, and Ureas of 4-Prop-2-ynylidenecycloalkylamine as Potent, Selective, and Bioavailable Negative Allosteric Modulators of Metabotropic Glutamate Receptor 5.,  62  (3): [PMID:30624919] [10.1021/acs.jmedchem.8b01226]

Source

Source(1):

• Scientific Literature