Page last updated: 2024-12-07

rubimaillin

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

Description

rubimaillin: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID124219
CHEMBL ID446008
CHEBI ID141063
SCHEMBL ID2115949
MeSH IDM0134078

Synonyms (37)

Synonym
rubimaillin
ccris 6432
2h-naphtho(1,2-b)pyran-5-carboxylic acid, 6-hydroxy-2,2-dimethyl-, methyl ester
mollugin
methyl 6-hydroxy-2,2-dimethylbenzo[h]chromene-5-carboxylate
CHEMBL446008
CHEBI:141063
55481-88-4
methyl 6-hydroxy-2,2-dimethyl-2h-benzo[h]chromene-5-carboxylate
SCHEMBL2115949
S9162
FT-0688300
m98n6a8z2f ,
unii-m98n6a8z2f
3'-carbomethoxy-4'-hydroxy-6,6-dimethylnaphtho(1',2'-2,3)pyran
AKOS015897118
c17h16o4
methyl 6-hydroxy-2,2-dimethyl-benzo[h]chromene-5-carboxylate
AC-34129
Q-100638
2h-naphtho[1,2-b]pyran-5-carboxylate, 2,2-dimethyl-6-hydroxy-, methyl ester
methyl 6-hydroxy-2,2-dimethyl-2h-benzo[h]chromene-5-carboxylate #
VLGATXOTCNBWIT-UHFFFAOYSA-N
rubimailin
DTXSID30204059
methyl 6-hydroxy-2,2-dimethyl-2h-benzeno[h]chromene-5-carboxylate
mollugin, >=98% (hplc)
M3091
HY-N0316
mfcd02752331
mollugin,(s)
A14851
CCG-267302
CS-0008814
BS-49147
A870182
Z3234884822

Research Excerpts

Overview

Rubimaillin (Rub) is a naphthoquinone compound extracted from Chinese herbal medicine. It has various biological activities.

ExcerptReferenceRelevance
"Rubimaillin (Rub) is a naphthoquinone compound extracted from Chinese herbal medicine, and it has various biological activities."( Analgesic action of Rubimaillin in vitro and in vivo.
Fan, F; Jiang, Z; Yan, W, 2020
)
1.6

Pharmacokinetics

ExcerptReferenceRelevance
"A specific, simple, sensitive Ultra High Performance Liquid Chromatography-tandem Mass Spectrometry (UHPLC-MS/MS) method has been developed and validated for the simultaneous determination and pharmacokinetic study of purpurin, munjistin, and mollugin in rat plasma."( Simultaneous Determination of Purpurin, Munjistin and Mollugin in Rat Plasma by Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry: Application to a Pharmacokinetic Study after Oral Administration of Rubia cordifolia L. Extract.
Gao, M; Kuang, H; Liu, L; Wang, L; Wang, Z; Yang, B; Yang, C; Yang, J, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
acyl-CoA:cholesterol acyltransferase 2 inhibitorA sterol O-acyltransferase inhibitor that specifically inhibits acyl-CoA:cholesterol acyltransferase 2.
NF-kappaB inhibitorAn inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
neuroprotective agentAny compound that can be used for the treatment of neurodegenerative disorders.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
[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 (3)

ClassDescription
benzochromene
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
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]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (49)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IINAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
base-excision repairNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
double-strand break repairNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromatin remodelingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein deacetylationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of cell population proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
determination of adult lifespanNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
response to UVNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
retrotransposon silencingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of double-strand break repair via homologous recombinationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of lipid metabolic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
pericentric heterochromatin formationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
subtelomeric heterochromatin formationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein destabilizationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of insulin secretionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of telomere maintenanceNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of proteasomal ubiquitin-dependent protein catabolic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
circadian regulation of gene expressionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of transcription elongation by RNA polymerase IINAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
ketone biosynthetic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of protein import into nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
glucose homeostasisNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of circadian rhythmNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
post-translational protein modificationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of fat cell differentiationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of gluconeogenesisNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of gene expression, epigeneticNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of glycolytic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of glucose importNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of protein export from nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of fibroblast proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of protein secretionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of lipid catabolic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein delipidationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
cardiac muscle cell differentiationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of cold-induced thermogenesisNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of protein localization to chromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of protein localization to chromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
DNA repair-dependent chromatin remodelingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of stem cell population maintenanceNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of chondrocyte proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of protein localization to plasma membraneNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of blood vessel branchingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of vascular endothelial cell proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein localization to site of double-strand breakNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of stem cell proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of stem cell differentiationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of cellular senescenceNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of double-strand break repairNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
chromatin bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
damaged DNA bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+ ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
zinc ion bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleotidyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromatin DNA bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleosome bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent protein lysine deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein homodimerization activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone H3K9 deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+ bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone H3K18 deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+-protein-arginine ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
DNA damage sensor activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone H3K56 deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent protein demyristoylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent protein depalmitoylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+- protein-lysine ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
TORC2 complex bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+-protein ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
transcription corepressor activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
nucleolusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
pericentric heterochromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
endoplasmic reticulumNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
site of double-strand breakNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
site of DNA damageNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleoplasmNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
intracellular membrane-bounded organelleNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromosome, subtelomeric regionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID354698Antiviral activity against Hepatitis B virus infected in human Hep3B cells assessed as suppression of viral surface antigen secretion after 48 hrs by enzyme immunoassay1996Journal of natural products, Mar, Volume: 59, Issue:3
Inhibition of hepatitis B surface antigen secretion on human hepatoma cells. Components from Rubia cordifolia.
AID1665221Activation of N-terminal his-tagged human SIRT6 expressed in Escherichia coli M15 [pREP4] assessed as increase in peptide demyristoylation at 100 uM incubated for 120 mins using Ac-EALPKK(Myr)-AMC substrate by FDL assay relative to control2020Journal of medicinal chemistry, 09-24, Volume: 63, Issue:18
Discovery of Potent Small-Molecule SIRT6 Activators: Structure-Activity Relationship and Anti-Pancreatic Ductal Adenocarcinoma Activity.
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.
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.
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.
AID354701Cytotoxicity against human Hep3B cells at >20 mg/mL by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Inhibition of hepatitis B surface antigen secretion on human hepatoma cells. Components from Rubia cordifolia.
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.
AID332378Antiplatelet activity against rabbit platelet assessed as inhibition of arachidonic acid-induced platelet aggregation treated 3 mins before arachidonic acid challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID1665222Activation of N-terminal his-tagged human SIRT6 expressed in Escherichia coli M15 [pREP4] assessed as increase in peptide demyristoylation incubated for 120 mins using Ac-EALPKK(Myr)-AMC substrate by FDL assay relative to control2020Journal of medicinal chemistry, 09-24, Volume: 63, Issue:18
Discovery of Potent Small-Molecule SIRT6 Activators: Structure-Activity Relationship and Anti-Pancreatic Ductal Adenocarcinoma Activity.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (46)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.17)18.7374
1990's2 (4.35)18.2507
2000's8 (17.39)29.6817
2010's24 (52.17)24.3611
2020's11 (23.91)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.51

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 Index11.51 (24.57)
Research Supply Index3.85 (2.92)
Research Growth Index5.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.51)

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%
Other46 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]