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

ID: ALA551380

PubChem CID: 45269766

Max Phase: Preclinical

Molecular Formula: C27H34O10

Molecular Weight: 518.56

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)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C27H34O10/c1-3-35-26(33)22(27(34)36-4-2)19(17-10-9-15-7-5-6-8-16(15)11-17)12-18(29)13-20-23(30)25(32)24(31)21(14-28)37-20/h5-11,19-25,28,30-32H,3-4,12-14H2,1-2H3/t19?,20-,21+,23-,24+,25+/m0/s1

Standard InChI Key:  OLTMNFSLVUGKED-LVXLBCKOSA-N

Molfile:  

     RDKit          2D

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   11.6937    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4054    0.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9779    0.0635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1213    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4069   -0.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1186    0.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8344    1.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4069    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.1220    2.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8368    2.5379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4079    2.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5509    2.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2657    2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6897   -0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6883   -1.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1180   -0.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 29  2  0
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 14 16  1  1
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  7  1  1  1
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  4 18  1  0
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 37 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA551380

   diethyl 2-[1-naphthalen-2-yl-3-oxo-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: 518.56

Molecular Weight (Monoisotopic): 518.2152

AlogP: 0.86

#Rotatable Bonds: 11

Polar Surface Area: 159.82

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: 0.61

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