(E)-4-(4-chlorophenyl)-1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)but-3-en-2-one

ID: ALA551762

PubChem CID: 45272309

Max Phase: Preclinical

Molecular Formula: C15H17ClO5

Molecular Weight: 312.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(Cl)cc1)C[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H17ClO5/c16-10-4-1-9(2-5-10)3-6-11(17)7-13-15(20)14(19)12(18)8-21-13/h1-6,12-15,18-20H,7-8H2/b6-3+/t12-,13+,14+,15+/m1/s1

Standard InChI Key:  ONSPIITXJAAAAE-WTSOPZKSSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.6380   -4.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263   -5.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -4.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5013   -5.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263   -6.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3539   -5.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3539   -6.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6380   -6.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697   -6.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697   -7.4656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7856   -6.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4973   -6.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7856   -5.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697   -4.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9277   -5.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -4.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323   -4.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9095   -3.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018   -4.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3429   -3.7252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
  6 14  1  0
  6  1  1  1
  4 15  1  0
  1  2  1  0
 15 16  2  0
  2  3  1  0
 16 17  1  0
  3  4  2  0
 17 18  2  0
  2  5  2  0
 18 19  1  0
  6  7  1  0
 19 20  2  0
 20 15  1  0
  7  8  1  6
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA551762

   (E)-4-(4-chlorophenyl)-1-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]but-3-en-2-one

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: 312.75

Molecular Weight (Monoisotopic): 312.0765

AlogP: 0.79

#Rotatable Bonds: 4

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: ┄

CX LogP: 1.13

CX LogD: 1.13

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: 1.19

References

1. Bisht SS, Fatima S, Tamrakar AK, Rahuja N, Jaiswal N, Srivastava AK, Tripathi RP..  (2009)  Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity.,  19  (10): [PMID:19362832] [10.1016/j.bmcl.2009.03.136]

Source

Source(1):

• Scientific Literature