Structure Database (LMSD)
Common Name
Chrysophanol
Systematic Name
1,8-dihydroxy-3-methyl-9,10-anthracenedione
Synonyms
- Chrysophanic Acid
- Turkey Rhubarb
3D model of Chrysophanol
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
Chrysophanol is an anthraquinone that has been found in R. palmatum and has diverse biological activities.1,2,3 It induces necrosis in J5 human liver cancer cells when used at concentrations of 25, 50, 75, 100, and 200 µM.2 Chrysophanol (5, 10, and 50 µM) reduces LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2) and inhibits LPS-induced DNA oxidation in BV-2 microglia.3 In vivo, chrysophanol (5 mg/kg) decreases colonic levels of IL-6 and activation of NF-κB and reduces weight loss, diarrhea, and rectal bleeding in a mouse model of colitis induced by dextran sulfate (DSS).4 Chrysophanol (0.1, 1, and 10 mg/kg) increases survival, reduces brain tissue loss, and ameliorates motor balance deficits in a mouse model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).5
This information has been provided by Cayman Chemical
References
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Rheum rhabarbarum
(#3621)
Magnoliopsida
(#3398)
The constituents of rhubarb,
J Chem Soc Trans, 1911
J Chem Soc Trans, 1911
DOI:
10.1039/CT9119900946
Talaromyces islandicus
(#28573)
Eurotiomycetes
(#147545)
Studies in the biochemistry of micro-organisms. 81. The colouring matters of Penicillium islandicum Sopp. Part 2. Chrysophanic acid, 4:5-dihydroxy-2-methylanthraquinone.,
Biochem J, 1950
Biochem J, 1950
Pubmed ID:
16748635
String Representations
InChiKey (Click to copy)
LQGUBLBATBMXHT-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
SMILES (Click to copy)
C12C=C(C=C(O)C=1C(=O)C1=C(C=CC=C1O)C2=O)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
3
Aromatic Rings
2
Rotatable Bonds
0
Van der Waals Molecular Volume
223.22
Topological Polar Surface Area
74.60
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
2.18
Molar Refractivity
67.82
Admin
Created at
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Updated at
13th Mar 2025