Structure Database (LMSD)
Common Name
Cassic acid
Systematic Name
4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
Synonyms
- Rhein
- Rhubarb Yellow
- Monorhein
- Rheic acid
3D model of Cassic acid
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
Rhein is an anthraquinone derivative that has been found in R. rhabarbarum and is an active metabolite of diacerein that has diverse biological activities, including anticancer, antioxidant, and anti-inflammatory activities.1,2,3,4 It induces cell cycle arrest at the S phase and inhibits the proliferation of HepG2 cells when used at concentrations of 40 and 100 µM, respectively.1 Rhein (100 and 200 µM) also inhibits proliferation of MCF-7 and MDA-MB-435s breast cancer cells under normoxic and hypoxic conditions.2 It reduces controlled cortical impact-induced decreases in catalase and superoxide dismutase (SOD) activity and malondialdehyde (MDA), glutathione, and glutathione disulfide levels in the brain in a rat model of traumatic brain injury when administered at a dose of 12 mg/kg.3 Rhein (50 mg/kg per day) reduces cerulein-induced increases in serum TNF-α, IL-1β, and amylase levels, as well as reduces pancreatic glandular atrophy and fibrosis, in a mouse model of chronic pancreatitis.4
This information has been provided by Cayman Chemical
References
2. Xu, X., Lv, H., Xia, Z., et al. Rhein exhibits antioxidative effects similar to Rhubarb in a rat model of traumatic brain injury. BMC Complement. Altern. Med. 17(1), 140 (2017).
References
String Representations
InChiKey (Click to copy)
FCDLCPWAQCPTKC-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
SMILES (Click to copy)
C12C(O)=CC(C(=O)O)=CC=1C(=O)C1=C(C(O)=CC=C1)C2=O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
2
Rotatable Bonds
1
Van der Waals Molecular Volume
238.16
Topological Polar Surface Area
111.90
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
1.57
Molar Refractivity
70.04
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Created at
-
Updated at
27th Jul 2020