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

ID: ALA1095083

PubChem CID: 46224074

Max Phase: Preclinical

Molecular Formula: C19H18ClNO2S

Molecular Weight: 359.88

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H18ClNO2S/c20-16-8-6-14(7-9-16)18-11-19(22,15-4-2-1-3-5-15)10-17(23-18)12-24-13-21/h1-9,17-18,22H,10-12H2/t17-,18+,19-/m0/s1

Standard InChI Key:  FZAPPHMXVLWNFB-OTWHNJEPSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    6.3083  -10.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3083  -10.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0204  -11.3333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7324  -10.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7324  -10.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0204   -9.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -8.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134   -8.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5938   -7.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7621   -7.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3518   -8.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7738   -8.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -8.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5954  -11.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4462  -11.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1613  -10.9271    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8752  -11.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5875  -11.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820  -10.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1696  -11.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712  -12.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8912  -12.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007  -12.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583  -12.5807    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  3  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:

   

   ALA1095083

   (2R*,4R*,6S*)-2-(4-Chlorophenyl)tetrahydro-4-phenyl-6-(thiocyanatomethyl)-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: 359.88

Molecular Weight (Monoisotopic): 359.0747

AlogP: 4.66

#Rotatable Bonds: 4

Polar Surface Area: 53.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.81

Np Likeness Score: 0.13

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