Structure Database (LMSD)
Common Name
Chrysophanol 8-O-beta-D-glucoside
Systematic Name
Synonyms
3D model of Chrysophanol 8-O-beta-D-glucoside
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Pulmatin is an anthraquinone glycoside that has been found in R. emodi and has diverse biological activities.1,2,3 It inhibits protein tyrosine phosphatase 1B (PTP1B; IC50 = 18.34 µM) and yeast and rat intestinal α-glucosidase when used at a concentration of 50 µg/ml.1,2 Pulmatin (25 µM) increases insulin-induced glucose transport by 255% in L6 myotubes.1 It lowers plasma levels of total cholesterol, phospholipids, LDL, VLDL, and triglycerides in a rat model of Triton WR-1339-induced dyslipidemia when administered at a dose of 100 mg/kg.3
This information has been provided by Cayman Chemical
References
1. Lee, M.S., and Sohn, C.B. Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome. Biol. Pharm. Bull. 31(11), 2154-2157 (2008).
2. Babu, K.S., Tiwari, A.K., Srinivas, P.V., et al. Yeast and mammalian a-glucosidase inhibitory constituents from Himalayan rhubarb Rheum emodi Wall.ex Meisson. Bioorg. Med. Chem. Lett. 14(14), 3841-3845 (2004).
String Representations
InChiKey (Click to copy)
WMMOMSNMMDMSRB-JNHRPPPUSA-N
InChi (Click to copy)
InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1
SMILES (Click to copy)
C12C(=O)C3=C(C=C(C=C3O)C)C(=O)C=1C=CC=C2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
4
Aromatic Rings
2
Rotatable Bonds
3
Van der Waals Molecular Volume
358.61
Topological Polar Surface Area
155.82
Hydrogen Bond Donors
5
Hydrogen Bond Acceptors
9
logP
1.37
Molar Refractivity
103.60
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Updated at
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