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
LM ID
LMPK13040015
Formula
Exact Mass
Calculate m/z
284.03209
Status
Curated



Classification

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cassia (#53851)
Magnoliopsida (#3398)
Identification of the antibiotic substance from Cassia reticulata as 4,5-dihydroxyanthraquinone-2-carboxylic acid.,
J Biol Chem, 1949
Pubmed ID: 18123056

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
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Updated at
27th Jul 2020