(E)-4-phenyl-1-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)but-3-en-2-one

ID: ALA559970

PubChem CID: 45268905

Max Phase: Preclinical

Molecular Formula: C16H20O6

Molecular Weight: 308.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)C[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H20O6/c17-9-13-15(20)16(21)14(19)12(22-13)8-11(18)7-6-10-4-2-1-3-5-10/h1-7,12-17,19-21H,8-9H2/b7-6+/t12-,13+,14-,15+,16+/m0/s1

Standard InChI Key:  PCQTVJXNLYAPQD-HXEHUVJKSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   11.8247   -3.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5354   -4.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2502   -3.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9609   -4.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5354   -5.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6758   -3.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6758   -3.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3907   -2.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1055   -3.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1055   -3.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3907   -4.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1098   -4.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1098   -5.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8247   -5.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3949   -5.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3949   -6.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6801   -5.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9694   -5.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6801   -4.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3949   -3.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9694   -3.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2545   -4.3263    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
  4  6  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19 21  1  1
 21 22  1  0
 12 20  1  0
 12  1  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA559970

   (E)-4-phenyl-1-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-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: 308.33

Molecular Weight (Monoisotopic): 308.1260

AlogP: -0.50

#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: -0.10

CX LogD: -0.10

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: 1.28

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