2-Methyl-6-{3-[1-(phenylsulfonyl)piperidin-4-ylidene]prop-1-yn-1-yl}pyridine

ID: ALA4535967

PubChem CID: 57574904

Max Phase: Preclinical

Molecular Formula: C20H20N2O2S

Molecular Weight: 352.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(C#CC=C2CCN(S(=O)(=O)c3ccccc3)CC2)n1

Standard InChI:  InChI=1S/C20H20N2O2S/c1-17-7-5-9-19(21-17)10-6-8-18-13-15-22(16-14-18)25(23,24)20-11-3-2-4-12-20/h2-5,7-9,11-12H,13-16H2,1H3

Standard InChI Key:  QMHJUOODIJYSDC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.6041  -14.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1996  -15.1634    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0166  -15.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8381  -14.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370  -15.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450  -16.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2547  -15.6110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518  -14.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5432  -14.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448  -16.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580  -14.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6626  -13.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668  -13.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0779  -13.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0786  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856  -15.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4923  -14.7597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4874  -13.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7758  -13.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2057  -15.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4977  -16.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5034  -17.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2160  -17.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9244  -17.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9152  -16.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  6 10  1  0
  8 11  1  0
 11 12  3  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17  2  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535967

   2-[3-[1-(Benzenesulfonyl)piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine

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: 352.46

Molecular Weight (Monoisotopic): 352.1245

AlogP: 3.15

#Rotatable Bonds: 2

Polar Surface Area: 50.27

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.19

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -1.22

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