(E)-1-(beta-D-glucopyranosyl)-4-(4'-chlorophenyl)but-3-en-2-one

ID: ALA559775

PubChem CID: 45268904

Max Phase: Preclinical

Molecular Formula: C16H19ClO6

Molecular Weight: 342.78

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H19ClO6/c17-10-4-1-9(2-5-10)3-6-11(19)7-12-14(20)16(22)15(21)13(8-18)23-12/h1-6,12-16,18,20-22H,7-8H2/b6-3+/t12-,13+,14-,15+,16+/m0/s1

Standard InChI Key:  ROGJKLXFRUDIER-UDKWCLLRSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.1077   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2440   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184   -3.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9588   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9588   -1.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6737   -0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -1.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6737   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0993   -0.7979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -3.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -3.6814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -3.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -4.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631   -3.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523   -3.6814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -2.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626   -2.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  9 12  1  0
  4  6  1  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 20 22  1  1
 22 23  1  0
 13 21  1  0
 13  1  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA559775

   (E)-1-(beta-D-glucopyranosyl)-4-(4''-chlorophenyl)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: 342.78

Molecular Weight (Monoisotopic): 342.0870

AlogP: 0.15

#Rotatable Bonds: 5

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: 0.50

CX LogD: 0.50

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: 1.00

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