(2R*,4R*,6S*)-2-(4-Chlorophenyl)-6-((ethylthio)methyl)tetrahydro-4-phenyl-2H-pyran-4-ol

ID: ALA1095082

PubChem CID: 46224073

Max Phase: Preclinical

Molecular Formula: C20H23ClO2S

Molecular Weight: 362.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSC[C@@H]1C[C@@](O)(c2ccccc2)C[C@H](c2ccc(Cl)cc2)O1

Standard InChI:  InChI=1S/C20H23ClO2S/c1-2-24-14-18-12-20(22,16-6-4-3-5-7-16)13-19(23-18)15-8-10-17(21)11-9-15/h3-11,18-19,22H,2,12-14H2,1H3/t18-,19+,20-/m0/s1

Standard InChI Key:  FPGNAQGJVPLCGL-ZCNNSNEGSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.4875  -10.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875  -11.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755  -11.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0635  -11.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0635  -10.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755   -9.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958   -9.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -8.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -7.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0338   -7.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440   -8.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220   -9.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -9.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004  -11.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3496  -11.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655  -11.1312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793  -11.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944  -11.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139  -11.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6263  -11.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6246  -12.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046  -12.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1951  -12.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3375  -12.7848    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12  7  1  0
  5  6  1  0
  6 13  1  1
  2 14  1  1
  6  7  1  0
  4 15  1  1
  1  2  1  0
 15 16  1  0
  7  8  2  0
 16 17  1  0
  1  6  1  0
 17 18  1  0
  8  9  1  0
 14 19  2  0
  2  3  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  3  4  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 14  1  0
  4  5  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1095082

   (2R*,4R*,6S*)-2-(4-Chlorophenyl)-6-((ethylthio)methyl)tetrahydro-4-phenyl-2H-pyran-4-ol

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: 362.92

Molecular Weight (Monoisotopic): 362.1107

AlogP: 5.20

#Rotatable Bonds: 5

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 0.02

References

1. Singh P, Bhardwaj A..  (2010)  Mono-, di-, and triaryl substituted tetrahydropyrans as cyclooxygenase-2 and tumor growth inhibitors. Synthesis and biological evaluation.,  53  (9): [PMID:20387815] [10.1021/jm1001327]

Source

Source(1):

• Scientific Literature