Compounds > emodin anthrone
Page last updated: 2024-12-07

emodin anthrone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Emodin anthrone is a natural anthraquinone derivative found in various plants, including Rheum palmatum and Aloe vera. It exhibits a range of biological activities, including antioxidant, anti-inflammatory, and anticancer effects. Research suggests that emodin anthrone may act as a potent inhibitor of certain enzymes and signaling pathways involved in cancer cell growth and proliferation. Studies have also investigated its potential therapeutic applications in treating conditions like diabetes, cardiovascular disease, and Alzheimer's disease. Its synthesis involves a multi-step process, often starting from emodin, another anthraquinone compound. Due to its multifaceted biological activities and potential therapeutic benefits, emodin anthrone has garnered significant interest within the scientific community.'

emodin anthrone: inhibits respiratory-driven solute transport in membrane vesicles of E coli [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

emodin anthrone : A member of the class of anthracenones that is anthracen-9(10H)-one which carries a methyl group at position 6 and hydroxy groups at positions 1, 3 and 8, respectively. It is an intermediate precursor in the synthesis of hypericin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID122635
CHEMBL ID122192
CHEBI ID150013
SCHEMBL ID6046328
MeSH IDM0142847

Synonyms (36)

Synonym
AC-1208
1,6,8-trihydroxy-3-methyl-10-hydroanthracen-9-one
9(10h)-anthracenone, 1,3,8-trihydroxy-6-methyl-
491-60-1
emodinanthrone
1,3,8-trihydroxy-6-methyl-10h-anthracen-9-one
emodin anthrone
1,3,8-trihydroxy-6-methylanthrone
CHEMBL122192 ,
bdbm50060878
1,3,8-trihydroxy-6-methylanthracen-9(10h)-one
CHEBI:150013
emodin-9-anthrone
2,4,5-trihydroxy-7-methylanthracen-10(9h)-one
77c500w1a2 ,
unii-77c500w1a2
1,3,8,9-tetrahydroxy-6-methylanthracene
frangula emodin anthrone
anthrone, 1,3,8-trihydroxy-6-methyl-
LAJSXCAVRQXZIO-UHFFFAOYSA-N
SCHEMBL6046328
AKOS025401350
DTXSID80197684
1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracen-9-one
emodinol
emodinanthranol
protophyscihydrone
frangulaemodinanthrone
1,3,8-trihydroxy-6-methyl-9(10h)-anthracenone
frangulaemodinanthranol
emodinanthrone pound>>1,3,8-trihydroxy-6-methyl-10h-anthracen-9-one 1,6,8-trihydroxy-3-methyl-10-hydroanthracen-9-one 9(10h)-anthracenone
BCP29231
Q27266578
emodin anthranol
HY-N9362
CS-0159524

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Their biodistribution and pharmacokinetic properties were determined in rat models of induced necrosis."( Effects of skeleton structure on necrosis targeting and clearance properties of radioiodinated dianthrones.
Feng, Y; Gao, M; Huang, D; Jiang, C; Ni, Y; Shao, H; Sun, Z; Wang, X; Yang, S; Yin, Z; Zhang, D; Zhang, J, 2016)		0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
anthracenoneAny member of the class of anthracenes in which the anthracene moiety is substituted by an oxo group.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
cuticular wax biosynthesis28
hypericin biosynthesis17
hypericin biosynthesis18

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-lipoxygenase Bos taurus (cattle)IC50 (µMol)14.00000.18001.75824.0000AID160507
P2Y purinoceptor 12Homo sapiens (human)Ki10.00000.00202.82209.8300AID375433
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor signaling pathwayP2Y purinoceptor 12Homo sapiens (human)
monoatomic ion transportP2Y purinoceptor 12Homo sapiens (human)
substrate-dependent cell migration, cell extensionP2Y purinoceptor 12Homo sapiens (human)
G protein-coupled receptor signaling pathwayP2Y purinoceptor 12Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayP2Y purinoceptor 12Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayP2Y purinoceptor 12Homo sapiens (human)
hemostasisP2Y purinoceptor 12Homo sapiens (human)
calcium-mediated signalingP2Y purinoceptor 12Homo sapiens (human)
cerebral cortex radial glia-guided migrationP2Y purinoceptor 12Homo sapiens (human)
cell projection organizationP2Y purinoceptor 12Homo sapiens (human)
lamellipodium assemblyP2Y purinoceptor 12Homo sapiens (human)
platelet activationP2Y purinoceptor 12Homo sapiens (human)
positive regulation of integrin activation by cell surface receptor linked signal transductionP2Y purinoceptor 12Homo sapiens (human)
positive regulation of cell adhesion mediated by integrinP2Y purinoceptor 12Homo sapiens (human)
G protein-coupled purinergic nucleotide receptor signaling pathwayP2Y purinoceptor 12Homo sapiens (human)
positive regulation of monoatomic ion transportP2Y purinoceptor 12Homo sapiens (human)
response to axon injuryP2Y purinoceptor 12Homo sapiens (human)
regulation of chemotaxisP2Y purinoceptor 12Homo sapiens (human)
positive regulation of chemotaxisP2Y purinoceptor 12Homo sapiens (human)
establishment of localization in cellP2Y purinoceptor 12Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionP2Y purinoceptor 12Homo sapiens (human)
platelet aggregationP2Y purinoceptor 12Homo sapiens (human)
cellular response to ATPP2Y purinoceptor 12Homo sapiens (human)
visual system developmentP2Y purinoceptor 12Homo sapiens (human)
positive regulation of ruffle assemblyP2Y purinoceptor 12Homo sapiens (human)
regulation of microglial cell migrationP2Y purinoceptor 12Homo sapiens (human)
positive regulation of microglial cell migrationP2Y purinoceptor 12Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityP2Y purinoceptor 12Homo sapiens (human)
G protein-coupled ADP receptor activityP2Y purinoceptor 12Homo sapiens (human)
guanyl-nucleotide exchange factor activityP2Y purinoceptor 12Homo sapiens (human)
G protein-coupled purinergic nucleotide receptor activityP2Y purinoceptor 12Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneP2Y purinoceptor 12Homo sapiens (human)
cell surfaceP2Y purinoceptor 12Homo sapiens (human)
membraneP2Y purinoceptor 12Homo sapiens (human)
cell projection membraneP2Y purinoceptor 12Homo sapiens (human)
cell body membraneP2Y purinoceptor 12Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID85482Antiproliferative (inhibition of cell growth) activity against HaCaT cells (human keratinocyte line)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID1434015Inhibition of ATP citrate lyase (unknown origin) at 10 uM using sodium citrate as substrate after 60 mins by ADP-Glo luminescence assay relative to control2017European journal of medicinal chemistry, Jan-27, Volume: 126Design and synthesis of emodin derivatives as novel inhibitors of ATP-citrate lyase.
AID233179Antioxidant potential was assessed from reducing activity against 2,2,di-phenyl-1-picrylhydrazyl.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID472353Cytotoxicity against human THP1 cells after 48 hrs assessed morphological changes compound exposed to light for 20 mins before treatment2009Journal of natural products, Oct, Volume: 72, Issue:10
Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis.
AID472354Cytotoxicity against human THP1 cells after 48 hrs assessed as morphological changes in the dark condition2009Journal of natural products, Oct, Volume: 72, Issue:10
Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis.
AID85486Cytotoxic activity (2 uM) was measured by the amount of LDH (mU) release in HaCaT cells.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID19630Partition coefficient (logP)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID375434Displacement of [3H]PSB0413 from human platelet P2Y12 receptor at 10 uM2009Journal of medicinal chemistry, Jun-25, Volume: 52, Issue:12
High-affinity, non-nucleotide-derived competitive antagonists of platelet P2Y12 receptors.
AID1605075-LO inhibitory activity was determined by inhibition of LTB4 biosynthesis in bovine polymorphonuclear leukocytes (PMNL)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID357642Cytotoxicity against human KB cells2001Journal of natural products, Sep, Volume: 64, Issue:9
Cytotoxicity of Rhamnosylanthraquinones and Rhamnosylanthrones from Rhamnus nepalensis.
AID231071Peroxidant property was expressed as ratio of uMol of malondialdehyde and mMol of deoxyribose released by 75 uM test compound1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
AID375433Displacement of [3H]PSB0413 from human platelet P2Y12 receptor2009Journal of medicinal chemistry, Jun-25, Volume: 52, Issue:12
High-affinity, non-nucleotide-derived competitive antagonists of platelet P2Y12 receptors.
AID493017Wombat Data for BeliefDocking1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's3 (30.00)18.2507
2000's3 (30.00)29.6817
2010's3 (30.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.02

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.02 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pyrogallol
benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.		1.9910benzenetriol;
phenolic donor		plant metabolite
anthralin
Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.		1.9910anthracenesantipsoriatic
danthron
danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.		1.9910dihydroxyanthraquinoneapoptosis inducer;
plant metabolite
emodin
Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.		8.6390trihydroxyanthraquinoneantineoplastic agent;
laxative;
plant metabolite;
tyrosine kinase inhibitor
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.0510nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
hypericin
[no description available]		8.1350
juglone
juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.		1.9910hydroxy-1,4-naphthoquinonegeroprotector;
herbicide;
reactive oxygen species generator
mitoxantrone
Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.		2.0510dihydroxyanthraquinoneanalgesic;
antineoplastic agent
anthrone
anthrone: used in colorimetric determination of sugar & animal starch in body fluids; structure. anthrone : A member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9.		1.9910anthracenoneradical scavenger
anthracene
acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.		1.9910acene;
anthracenes;
ortho-fused tricyclic hydrocarbon
perylene
Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.		2.7430ortho- and peri-fused polycyclic arene;
perylenes
naphthazarin
naphthazarin: fish toxin; isolated for first time from the walnut onigurmi, Juglans mandshurica maxim var. Sieboldiana Makino; structure. naphthazarin : A naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups.		1.9910hydroxy-1,4-naphthoquinoneacaricide;
antibacterial agent;
antineoplastic agent;
apoptosis inducer;
geroprotector;
plant metabolite
aloe emodin
aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.		2.4120aromatic primary alcohol;
dihydroxyanthraquinone		antineoplastic agent;
plant metabolite
chrysophanic acid
chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.		2.4320dihydroxyanthraquinoneanti-inflammatory agent;
antiviral agent;
plant metabolite
physcione
physcione: structure. physcion : A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources.		2.4320dihydroxyanthraquinoneanti-inflammatory agent;
antibacterial agent;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
hepatoprotective agent;
metabolite
2,2'-Dihydroxybenzophenone
[no description available]		1.9910benzophenones
rhein-9-anthrone
rhein-9-anthrone: metabolite of sennosides A+B formed in the colon; structure given in first source		1.9910anthracenes
aloe emodin anthrone
aloe emodin anthrone: structure given in first source		1.9910anthracenes
protohypericin
protohypericin: structure in first source		2.4820
frangulin b
frangulin B: found in bark of Frangula alnus (formerly called Rhamnus frangula)		2.0510anthraquinone
alloin
alloin: isolated from various species of aloe; structure		2.4220diastereoisomeric mixtureEC 1.14.18.1 (tyrosinase) inhibitor;
laxative
3,5-dichloro-2-hydroxy-N-(2-methoxy-5-phenylphenyl)benzenesulfonamide
[no description available]		2.1510biphenyls
acid blue 40
Acid Blue 40: a textile dye; structure in first source		2.0510
acid blue 25
[no description available]		2.0510
acid blue 129
[no description available]		2.0510
tetracycline
Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.		2.0510
chlortetracycline
Chlortetracycline: A TETRACYCLINE with a 7-chloro substitution.. chlortetracycline : A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens.		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Palmoplantaris Pustulosis
[description not available]		01.9910
Psoriasis
A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.		01.9910
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		01.9910
Leucocythaemia
[description not available]		0210
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		0210
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1310
Cancer of Lung
[description not available]		02.1310
Lung Neoplasms
Tumors or cancer of the LUNG.		02.1310
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.1310