(R,S)-diethyl 2-(3-oxo-1-phenyl-4-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)butyl)malonate

ID: ALA560567

PubChem CID: 45268915

Max Phase: Preclinical

Molecular Formula: C23H32O10

Molecular Weight: 468.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(C(=O)OCC)C(CC(=O)C[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccccc1

Standard InChI:  InChI=1S/C23H32O10/c1-3-31-22(29)18(23(30)32-4-2)15(13-8-6-5-7-9-13)10-14(25)11-16-19(26)21(28)20(27)17(12-24)33-16/h5-9,15-21,24,26-28H,3-4,10-12H2,1-2H3/t15?,16-,17+,19-,20+,21+/m0/s1

Standard InChI Key:  RDWCZGNDHGWJRW-DXVIRTPJSA-N

Molfile:  

     RDKit          2D

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   -0.8305   -5.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -5.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -5.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305   -6.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2580   -6.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422   -7.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739   -7.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739   -7.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -6.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9739   -5.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0271   -5.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7419   -5.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0264   -6.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -5.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708   -5.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -4.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -4.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995   -4.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7426   -4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574   -4.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187   -7.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201   -7.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -8.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3118   -7.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -7.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 15  1  0
  7  1  1  1
  4 18  1  0
  1  2  1  0
  6 19  1  0
  2  3  1  0
 19 20  1  0
  3  4  1  0
 19 21  2  0
  2  5  2  0
 20 22  1  0
  4  6  1  0
 22 23  1  0
  7  8  1  0
  6 24  1  0
  8  9  1  6
 24 25  1  0
  8 10  1  0
 24 26  2  0
 10 11  1  1
 25 27  1  0
 10 12  1  0
 27 28  1  0
 12 13  1  6
 18 29  2  0
 12 14  1  0
 29 30  1  0
 14 15  1  0
 30 31  2  0
 14 16  1  1
 31 32  1  0
 16 17  1  0
 32 33  2  0
 33 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA560567

   diethyl 2-[3-oxo-1-phenyl-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butyl]propanedioate

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: 468.50

Molecular Weight (Monoisotopic): 468.1995

AlogP: -0.30

#Rotatable Bonds: 11

Polar Surface Area: 159.82

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: -0.03

CX LogD: -0.03

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: 0.65

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