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

ID: ALA1096037

PubChem CID: 46224071

Max Phase: Preclinical

Molecular Formula: C20H23FO2S

Molecular Weight: 346.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H23FO2S/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:  CBOPNSRBBJCEGV-ZCNNSNEGSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.8792   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5912   -5.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3032   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3032   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5912   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -3.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5843   -2.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1646   -1.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -2.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3447   -3.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9958   -3.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1663   -5.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0171   -5.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7321   -5.0687    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4460   -5.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1611   -5.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -5.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404   -5.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420   -6.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4621   -6.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -6.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -6.7223    0.0000 F   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:

   

   ALA1096037

   (2S*,4R*,6R*)-2-((Ethylthio)methyl)-6-(4-fluorophenyl)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: 346.47

Molecular Weight (Monoisotopic): 346.1403

AlogP: 4.69

#Rotatable Bonds: 5

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: -0.08

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