(E)-1-(beta-D-xylopyranosyl)-4-(3,4-dimethoxyphenyl)but-3-en-2-one

ID: ALA561166

PubChem CID: 45268925

Max Phase: Preclinical

Molecular Formula: C17H22O7

Molecular Weight: 338.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)C[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)cc1OC

Standard InChI:  InChI=1S/C17H22O7/c1-22-13-6-4-10(7-14(13)23-2)3-5-11(18)8-15-17(21)16(20)12(19)9-24-15/h3-7,12,15-17,19-21H,8-9H2,1-2H3/b5-3+/t12-,15+,16+,17+/m1/s1

Standard InChI Key:  QJFIZZLOWVBGJH-TVWIMWAGSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    9.9162   -5.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6279   -6.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3437   -5.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0554   -6.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6279   -6.9781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2003   -6.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2003   -6.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9162   -7.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4844   -7.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4844   -8.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7686   -6.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0569   -7.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7686   -6.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4844   -5.7406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7674   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4819   -6.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1926   -5.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1864   -4.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4637   -4.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7560   -4.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4542   -3.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1639   -3.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8971   -4.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6153   -4.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 19 21  1  0
  7  9  1  0
 21 22  1  0
  9 10  1  1
 18 23  1  0
  9 11  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA561166

   (E)-4-(3,4-dimethoxyphenyl)-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: 338.36

Molecular Weight (Monoisotopic): 338.1366

AlogP: 0.16

#Rotatable Bonds: 6

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: ┄

CX LogP: 0.21

CX LogD: 0.21

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: 1.34

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