(Ss,Rc)-2-Amino-3-cyano-4-p-chloroyphenyl-6-(2-pyridyl)-5-ptolylsulfinyl-4H-pyran

ID: ALA4218818

PubChem CID: 145970085

Max Phase: Preclinical

Molecular Formula: C24H18ClN3O2S

Molecular Weight: 447.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc([S@+]([O-])C2=C(c3ccccn3)OC(N)=C(C#N)[C@H]2c2ccc(Cl)cc2)cc1

Standard InChI:  InChI=1S/C24H18ClN3O2S/c1-15-5-11-18(12-6-15)31(29)23-21(16-7-9-17(25)10-8-16)19(14-26)24(27)30-22(23)20-4-2-3-13-28-20/h2-13,21H,27H2,1H3/t21-,31+/m1/s1

Standard InChI Key:  CWLWRNDCAJBTOF-UKPGIYTDSA-N

Molfile:  

     RDKit          2D

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    4.9375  -20.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375  -21.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494  -22.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3614  -21.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3614  -20.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494  -20.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2218  -20.4602    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086  -20.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494  -19.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660  -19.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664  -18.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6513  -17.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9346  -18.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0739  -20.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7895  -20.0491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7934  -20.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0807  -20.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827  -21.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8033  -22.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5131  -21.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3499  -22.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507  -22.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635  -22.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1747  -23.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785  -23.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622  -23.0744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0753  -22.1091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700  -22.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194  -19.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6502  -17.1554    0.0000 Cl  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  2  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  6  9  1  6
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  3  0
  5 15  1  0
  8 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  4 28  1  0
 19 29  1  0
  7 30  1  6
 12 31  1  0
M  CHG  2   7   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4218818

   ---

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: 447.95

Molecular Weight (Monoisotopic): 447.0808

AlogP: 5.03

#Rotatable Bonds: 4

Polar Surface Area: 94.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.82

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -1.09

References

1. Recio R, Vengut-Climent E, Mouillac B, Orcel H, López-Lázaro M, Calderón-Montaño JM, Álvarez E, Khiar N, Fernández I..  (2017)  Design, synthesis and biological studies of a library of NK1-Receptor Ligands Based on a 5-arylthiosubstituted 2-amino-4,6-diaryl-3-cyano-4H-pyran core: Switch from antagonist to agonist effect by chemical modification.,  138  [PMID:28710964] [10.1016/j.ejmech.2017.06.056]

Source

Source(1):

• Scientific Literature