Compounds > rhein-9-anthrone
Page last updated: 2024-12-07

rhein-9-anthrone

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

Description

rhein-9-anthrone: metabolite of sennosides A+B formed in the colon; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119396
CHEMBL ID421615
CHEBI ID174546
SCHEMBL ID12774642
MeSH IDM0157045

Synonyms (27)

Synonym
4,5-dihydroxy-10-oxo-9,10-dihydroanthracene-2-carboxylic acid
CHEBI:174546
NCI60_020625
nsc-658580
rheinanthrone
2-anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-10-oxo-
rhein-9-anthrone
nsc658580
4,5-dihydroxy-10-oxo-9h-anthracene-2-carboxylic acid
480-09-1
CHEMBL421615 ,
bdbm50060855
4,5-dihydroxy-10-oxo-9,10-dihydro-anthracene-2-carboxylic acid
unii-0yqk3wbh32
nsc 658580
4,5-dihydroxy-10-oxo-9,10-dihydro-2-anthracenecarboxylic acid
0yqk3wbh32 ,
2-anthracenecarboxylicacid, 9,10-dihydro-4,5-dihydroxy-10-oxo-
SCHEMBL12774642
DTXSID10197374
9,10-dihydro-4,5-dihydroxy-10-oxo-2-anthroic acid, 8ci
DB13175
monorheinanthron
1,8-dihydroxy-9-anthrone-3-carboxylic acid
2-anthroic acid, 9,10-dihydro-4,5-dihydroxy-10-oxo-
9,10-dihydro-4,5-dihydroxy-10-oxo-2-anthracenecarboxylic acid
Q16888506
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
anthracenesCompounds containing an anthracene skeleton.
[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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-lipoxygenase Bos taurus (cattle)IC50 (µMol)3.00000.18001.75824.0000AID160507
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
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.
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.
AID19630Partition coefficient (logP)1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (18.18)18.7374
1990's16 (72.73)18.2507
2000's0 (0.00)29.6817
2010's2 (9.09)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: 11.58

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.58 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (87.50%)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.		2.0710trihydroxyanthraquinoneantineoplastic agent;
laxative;
plant metabolite;
tyrosine kinase inhibitor
hypericin
[no description available]		1.9910
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		3.0950aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
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
sennoside a&b
[no description available]		4.4870
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
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
rhein
[no description available]		3.77110dihydroxyanthraquinone
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.		2.0710aromatic primary alcohol;
dihydroxyanthraquinone		antineoplastic agent;
plant metabolite
dibenz(b,f)(1,4)oxazepine-10(11h)-carboxylic acid, 8-chloro-, 2-acetylhydrazide
Dibenz(b,f)(1,4)oxazepine-10(11H)-carboxylic acid, 8-chloro-, 2-acetylhydrazide: Inhibits the activity of prostaglandins.		2.3820
bw-755c
4,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine: A dual inhibitor of both cyclooxygenase and lipoxygenase pathways. It exerts an anti-inflammatory effect by inhibiting the formation of prostaglandins and leukotrienes. The drug also enhances pulmonary hypoxic vasoconstriction and has a protective effect after myocardial ischemia.		2.3820
2,2'-Dihydroxybenzophenone
[no description available]		1.9910benzophenones
sennidin a
dihydroxydianthrone: aglycone of senna glycosides		1.9710
1-hexadecyl-2-acetyl-glycero-3-phosphocholine
Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.		2.38202-acetyl-1-alkyl-sn-glycero-3-phosphocholineantihypertensive agent;
beta-adrenergic antagonist;
bronchoconstrictor agent;
hematologic agent;
vasodilator agent
emodin anthrone
emodin anthrone: inhibits respiratory-driven solute transport in membrane vesicles of E coli. 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.		1.9910anthracenone;
phenols		fungal metabolite
aloe emodin anthrone
aloe emodin anthrone: structure given in first source		1.9910anthracenes
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		3.0850prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
alloin
alloin: isolated from various species of aloe; structure		1.9910diastereoisomeric mixtureEC 1.14.18.1 (tyrosinase) inhibitor;
laxative
calcimycin
Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.		1.9810benzoxazole
acid phosphatase
Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.		1.9810
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
Cancer of Colon
[description not available]		02.110
Colonic Neoplasms
Tumors or cancer of the COLON.		02.110
Diarrhea
An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.		02.9140
Colonic Inertia
Symptom characterized by the passage of stool once a week or less.		02.0710
Constipation
Infrequent or difficult evacuation of FECES. These symptoms are associated with a variety of causes, including low DIETARY FIBER intake, emotional or nervous disturbances, systemic and structural disorders, drug-induced aggravation, and infections.		02.0710
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		01.9810
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9810
Electrolytes
Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)		02.3820
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		01.9710