Compounds > 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone
Page last updated: 2024-11-11

1,3,6-trihydroxy-2-methyl-9,10-anthraquinone

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

Description

2-methyl-1,3,6-trihydroxy-9,10-anthraquinone: anthraquinone derivative [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,3,6-trihydroxy-2-methyl-9,10-anthraquinone : A trihydroxyanthraquinone that is 9,10-anthraquinone substituted by hydroxy groups at positions 1, 3 and 6 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis. [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]

FloraRankFlora DefinitionFamilyFamily Definition
RubiagenusA plant genus of the family RUBIACEAE. The root is a source of red dyes (madder color and 1,2,4-trihydroxy-9,10-anthracenedione) and ANTHRAQUINONES.[MeSH]RubiaceaeThe Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]

Cross-References

ID SourceID
PubMed CID5319801
CHEMBL ID251491
CHEBI ID69519
SCHEMBL ID22719980

Synonyms (19)

Synonym
CHEMBL251491
chebi:69519 ,
1,3,6-trihydroxy-2-methylanthracene-9,10-dione
1,3,6-trihydroxy-2-methyl-9,10-anthraquinone
9,10-anthracenedione, 1,3,6-trihydroxy-2-methyl-
6-hydroxyrubiadin
1,3,6-trihydroxy-2-methylanthraquinone
87686-86-0
AKOS028108773
Q27137858
FS-9124
1,3,6-trihydroxy-2-methyl-9,10-anthracenedione; 1,3,6-trihydroxy-2-methylanthraquinone; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone; 2-methyl-1,3,6-trihydroxyanthraquinone
FT-0775879
SCHEMBL22719980
E88682
CS-0023190
DTXSID701257045
2-methyl-1,3,6-trihydroxy-9,10-anthraquinone
HY-N2714
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (1)

ClassDescription
trihydroxyanthraquinoneA member of the class of hydroxyanthraquinones carrying three hydroxy substituents.
[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]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID355821Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 10 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID623563Antibacterial activity against Staphylococcus aureus CGMCC1.2465 after 24 hrs by turbidimetric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis.
AID355820Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 3 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID355819Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 1 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID332370Inhibition of thrombin-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before thrombin challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID355823Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 100 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID312305Chemoprevention index, ratio of IC50 for mouse Hepa lclc7 cells to activity against mouse quinone reductase2007Journal of natural products, Dec, Volume: 70, Issue:12
Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots.
AID355825Toxicity in lipopolysaccharide-activated ddY mouse macrophages at 100 uM by MTT method2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID312303Induction of mouse quinone reductase in mouse Hepa lclc7 cells assessed as concentration required to double enzyme activity2007Journal of natural products, Dec, Volume: 70, Issue:12
Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots.
AID623564Antifungal activity against Candida albicans CGMCC 2.2086 after 24 hrs by turbidimetric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis.
AID332373Inhibition of platelet activating factor-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before platelet activating factor challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID332379Antiplatelet activity against rabbit platelet assessed as inhibition of collagen-induced platelet aggregation treated 3 mins before collagen challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID332371Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before arachidonic acid challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID312304Cytotoxicity against mouse Hepa lclc7 cells2007Journal of natural products, Dec, Volume: 70, Issue:12
Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots.
AID332372Inhibition of collagen-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before collagen challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID355822Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 30 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's2 (40.00)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: 12.87

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 Index12.87 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.87)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		1.9810benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
ampicillin
Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.		2.0610beta-lactam antibiotic;
penicillin allergen;
penicillin		antibacterial drug
alizarin
[no description available]		2.0310dihydroxyanthraquinonechromophore;
dye;
plant metabolite
vanillic acid
Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.		2.0110methoxybenzoic acid;
monohydroxybenzoic acid		plant metabolite
2-methoxy-1,4-naphthoquinone
2-methoxy-1,4-naphthoquinone: isolated from Swertia calycina; structure in first source. 2-methoxy-1,4-naphthoquinone : A naphthoquinone that is naphthalene-1,4-dione substituted by a methoxy group at position 2. It has been isolated from the roots of Rubia yunnanensis.		2.06101,4-naphthoquinones;
enol ether		antimicrobial agent;
metabolite;
plant metabolite
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.0610delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0610taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
secoisolariciresinol
secoisolariciresinol: RN given refers to ((R-(R*,R*))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.		2.0110secoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
miconazole nitrate
miconazole nitrate : A racemate composed of equimolar amounts of (R)- and (S)-miconazole nitrate. An antifungal used for the treatment of athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.		2.0610
rubiadin
rubiadin: highly genotoxic in Salmonella typhimurium. rubiadin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 3 and a methyl group at position 2. It has been isolated from Rubia yunnanensis.		2.0310dihydroxyanthraquinoneantibacterial agent;
antioxidant;
hepatoprotective agent;
plant metabolite
rubimaillin
rubimaillin: structure given in first source. rubimaillin : A benzochromene that is 2H-benzo[h]chromene which is substituted by two methyl groups at position 2, a methoxycarbonyl group at position 5, and a hydroxy group at position 6. Found in the Chinese medical plant Rubia cordifola, It has an anti-cancer effect by inhibition of TNF-alpha-induced NF-kappaB activation. It is also a dual inhibitor of acyl-CoA:cholesterol acyltransferase 1 and 2 (ACAT1 and ACAT2), but is more selective for the ACAT2 isozyme.		1.9810benzochromene;
methyl ester;
phenols		acyl-CoA:cholesterol acyltransferase 2 inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
neuroprotective agent;
NF-kappaB inhibitor;
plant metabolite
omega-n-methylarginine
omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.		2.0110amino acid zwitterion;
arginine derivative;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid
lucidin 3-o-beta-primveroside
lucidin 3-O-beta-primveroside: structure given in first source		1.9810
isolariciresinol
isolariciresinol: RN given refers to ((1-S-(1alpha,2beta,3alpha))-isomer); structure given in first source. (+)-isolariciresinol : A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.		2.0110guaiacols;
lignan;
polyphenol;
primary alcohol		plant metabolite
1-hydroxy-2-methylanthraquinone
1-hydroxy-2-methylanthraquinone: from root of Prismatomeris tetrandra. 1-hydroxy-2-methyl-9,10-anthraquinone : A member of the class of hydroxyanthraquinones that is anthracene-9,10-dione substituted by a hydroxy group at position 1 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis.		1.9810monohydroxyanthraquinoneplant metabolite
lariciresinol
lariciresinol: found in human urine. (+)-lariciresinol : A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).		2.0110aromatic ether;
lignan;
oxolanes;
phenols;
primary alcohol		antifungal agent;
plant metabolite
isoliquiritigenin
[no description available]		2.0310chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
ConditionIndicatedRelationship StrengthStudiesTrials