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

ID: ALA564635

PubChem CID: 45268037

Max Phase: Preclinical

Molecular Formula: C25H36O12

Molecular Weight: 528.55

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)c1ccc(OC)c(OC)c1

Standard InChI:  InChI=1S/C25H36O12/c1-5-35-24(31)20(25(32)36-6-2)15(13-7-8-16(33-3)17(9-13)34-4)10-14(27)11-18-21(28)23(30)22(29)19(12-26)37-18/h7-9,15,18-23,26,28-30H,5-6,10-12H2,1-4H3/t15?,18-,19+,21-,22+,23+/m0/s1

Standard InChI Key:  ASLVIJCCFFAXMT-WIPWOYJKSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA564635

   diethyl 2-[1-(3,4-dimethoxyphenyl)-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: 528.55

Molecular Weight (Monoisotopic): 528.2207

AlogP: -0.28

#Rotatable Bonds: 13

Polar Surface Area: 178.28

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: -0.35

CX LogD: -0.35

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.19

Np Likeness Score: 0.68

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