6-(beta-D-glucopyranosyl)-2-carbethoxy-3-((R,S)4''-phenyl)-5-oxo-ethylhexanoate

ID: ALA549414

PubChem CID: 45270587

Max Phase: Preclinical

Molecular Formula: C23H31ClO10

Molecular Weight: 502.94

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(Cl)cc1

Standard InChI:  InChI=1S/C23H31ClO10/c1-3-32-22(30)18(23(31)33-4-2)15(12-5-7-13(24)8-6-12)9-14(26)10-16-19(27)21(29)20(28)17(11-25)34-16/h5-8,15-21,25,27-29H,3-4,9-11H2,1-2H3/t15?,16-,17+,19-,20+,21+/m0/s1

Standard InChI Key:  BVCMHWWPZJJODU-DXVIRTPJSA-N

Molfile:  

     RDKit          2D

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    1.5970    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118    2.5671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8829    2.5683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7407    2.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8778   -2.3787    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA549414

   diethyl 2-[1-(4-chlorophenyl)-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: 502.94

Molecular Weight (Monoisotopic): 502.1606

AlogP: 0.36

#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: 0.57

CX LogD: 0.57

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.25

Np Likeness Score: 0.48

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