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

ID: ALA557086

PubChem CID: 44187734

Max Phase: Preclinical

Molecular Formula: C19H26O9

Molecular Weight: 398.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)C[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H26O9/c1-25-13-6-10(7-14(26-2)19(13)27-3)4-5-11(21)8-12-16(22)18(24)17(23)15(9-20)28-12/h4-7,12,15-18,20,22-24H,8-9H2,1-3H3/b5-4+/t12-,15+,16-,17+,18+/m0/s1

Standard InChI Key:  NDHRABWBLXURQY-JQHRHNRZSA-N

Molfile:  

     RDKit          2D

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    0.5554  -23.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661  -23.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1594  -24.2984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810  -23.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810  -22.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959  -21.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2999  -24.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999  -25.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7254  -23.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4403  -23.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959  -21.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093  -20.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240  -21.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8377  -22.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240  -23.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237  -24.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
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 17 19  1  0
 19 20  1  0
 19 21  1  1
 21 22  1  0
 12 20  1  0
 12  1  1  1
  8 23  1  0
  1  2  1  0
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  2  3  1  0
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  3  4  2  0
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  2  5  2  0
 10 27  1  0
  6  7  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA557086

   (E)-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-(3,4,5-trimethoxyphenyl)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: 398.41

Molecular Weight (Monoisotopic): 398.1577

AlogP: -0.47

#Rotatable Bonds: 8

Polar Surface Area: 134.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: -0.58

CX LogD: -0.58

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.43

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