(E)-((2R,3S,4S,5R,6S)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 3-(4-hydroxyphenyl)acrylate

ID: ALA3960983

PubChem CID: 5321781

Max Phase: Preclinical

Molecular Formula: C21H22O10

Molecular Weight: 434.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1)OC[C@H]1O[C@@H](Oc2cc(O)cc(O)c2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C21H22O10/c22-12-4-1-11(2-5-12)3-6-17(25)29-10-16-18(26)19(27)20(28)21(31-16)30-15-8-13(23)7-14(24)9-15/h1-9,16,18-24,26-28H,10H2/b6-3+/t16-,18-,19+,20-,21-/m1/s1

Standard InChI Key:  XUJRENMDCSKMFE-JSYAWONVSA-N

Molfile:  

     RDKit          2D

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   15.2440  -25.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3960983

   [(2R,3S,4S,5R,6S)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

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: 434.40

Molecular Weight (Monoisotopic): 434.1213

AlogP: 0.25

#Rotatable Bonds: 6

Polar Surface Area: 166.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.97

CX Basic pKa: ┄

CX LogP: 1.52

CX LogD: 1.51

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: 1.68

References

1. Zhang X, Chen C, Li Y, Chen D, Dong L, Na W, Wu C, Zhang J, Li Y..  (2016)  Tadehaginosides A-J, Phenylpropanoid Glucosides from Tadehagi triquetrum, Enhance Glucose Uptake via the Upregulation of PPARγ and GLUT-4 in C2C12 Myotubes.,  79  (5): [PMID:27100993] [10.1021/acs.jnatprod.5b00820]

Source

Source(1):

• Scientific Literature