3,4,5-Trihydroxy-benzoic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxy-phenyl)-vinyl]-phenoxy}-tetrahydro-pyran-2-ylmethyl ester

ID: ALA113598

Chembl Id: CHEMBL113598

Cas Number: 94356-23-7

PubChem CID: 10076782

Max Phase: Preclinical

Molecular Formula: C28H28O13

Molecular Weight: 572.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/c2cc(O)cc(O[C@@H]3O[C@H](COC(=O)c4cc(O)c(O)c(O)c4)[C@@H](O)[C@H](O)[C@H]3O)c2)cc1O

Standard InChI:  InChI=1S/C28H28O13/c1-38-21-5-4-13(8-18(21)30)2-3-14-6-16(29)11-17(7-14)40-28-26(36)25(35)24(34)22(41-28)12-39-27(37)15-9-19(31)23(33)20(32)10-15/h2-11,22,24-26,28-36H,12H2,1H3/b3-2+/t22-,24-,25+,26-,28-/m1/s1

Standard InChI Key:  HEOKFDGOFROELJ-XJVIDBJFSA-N

Alternative Forms

1. Parent:

   

   ALA113598

   Rhaponticin 6''-O-gallate

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: 572.52

Molecular Weight (Monoisotopic): 572.1530

AlogP: 1.44

#Rotatable Bonds: 8

Polar Surface Area: 215.83

Molecular Species: NEUTRAL

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.01

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.11

Np Likeness Score: 1.42

References

1. Matsuda H, Kageura T, Morikawa T, Toguchida I, Harima S, Yoshikawa M..  (2000)  Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages.,  10  (4): [PMID:10714491] [10.1016/s0960-894x(99)00702-7]

2. Park S, Kim YN, Kwak HJ, Jeong EJ, Kim SH..  (2018)  Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné.,  28  (4): [PMID:29402747] [10.1016/j.bmcl.2018.01.063]

Source

Source(1):

• Scientific Literature