Structure Database (LMSD)

Common Name
Chrysophanol
Systematic Name
1,8-dihydroxy-3-methyl-9,10-anthracenedione
Synonyms
  • Chrysophanic Acid
  • Turkey Rhubarb
LM ID
LMPK13040006
Formula
Exact Mass
Calculate m/z
254.05791
Status
Curated

Classification

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
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
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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

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

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Created at
-
Updated at
13th Mar 2025