Compounds > 2-hydroxyjuglone
Page last updated: 2024-11-05

2-hydroxyjuglone

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

Description

2-Hydroxyjuglone is a natural product found in plants of the Juglandaceae family, such as walnut and hickory. It exhibits a wide range of biological activities, including antioxidant, antimicrobial, and anticancer properties. It is synthesized through a complex pathway involving the oxidation of juglone, another natural product found in these plants. The compound is known to interact with various biological targets, including enzymes, DNA, and cell membranes. Research focuses on understanding its mechanisms of action and exploring its potential applications in medicine and agriculture. The unique structure and biological properties of 2-hydroxyjuglone make it a valuable compound for further study.'

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

Cross-References

ID SourceID
PubMed CID21035
CHEMBL ID1089486
CHEMBL ID1576702
SCHEMBL ID109904
SCHEMBL ID8663341
MeSH IDM0379892

Synonyms (24)

Synonym
2,5-dihydroxynaphthoquinone
1,4-naphthalenedione, 2,5-dihydroxy-
brn 2049199
2-hydroxyjuglone
1,4-naphthoquinone, 2,5-dihydroxy-
2,5-dihydroxy-1,4-naphthalenedione
4,5-dihydroxynaphthalene-1,2-dione
CHEMBL1089486
NCGC00246349-01
AKOS006275567
CHEMBL1576702
4923-55-1
4-08-00-02949 (beilstein handbook reference)
SCHEMBL109904
SCHEMBL8663341
2,5-dihydroxy-1,4-naphthoquinone
WQASGOZUYRFMDF-UHFFFAOYSA-N
2,5-dihydroxynaphthalene-1,4-dione
mfcd01081395
DS-11554
DTXSID20964190
STL564656
O10612
CS-0332005
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency7.07950.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency6.29460.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency6.30960.177814.390939.8107AID2147
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency28.18380.125919.1169125.8920AID2549
phosphopantetheinyl transferaseBacillus subtilisPotency17.78280.141337.9142100.0000AID1490
ATAD5 protein, partialHomo sapiens (human)Potency10.31830.004110.890331.5287AID504467
Microtubule-associated protein tauHomo sapiens (human)Potency14.12540.180013.557439.8107AID1460
thioredoxin glutathione reductaseSchistosoma mansoniPotency50.11870.100022.9075100.0000AID485364
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency19.95260.28189.721235.4813AID2326
serine-protein kinase ATM isoform aHomo sapiens (human)Potency0.79430.707925.111941.2351AID485349
DNA polymerase betaHomo sapiens (human)Potency15.84890.022421.010289.1251AID485314
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency5.01190.00419.962528.1838AID2675
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency0.44670.251215.843239.8107AID504327
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
prothrombinHomo sapiens (human)IC50 (µMol)50.00000.00103.317014.6895AID1215
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1125073Cytotoxicity against human HeLa cells assessed as cell viability after 24 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID476716Growth inhibition of human T47D cells after 48 hrs by sulforhodamine B assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
AID1125075Cytotoxicity against tumor promotion-sensitive mouse JB6 Cl41 cells assessed as cell viability after 48 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID1125074Cytotoxicity against human HeLa cells assessed as cell viability after 48 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID476712Growth inhibition of human A2780 cells after 48 hrs by sulforhodamine B assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
AID1125077Ratio of IC50 to INCC50 for human HeLa cells2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID476714Growth inhibition of human HeLa cells after 48 hrs by sulforhodamine B assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
AID476715Growth inhibition of human SW1573 cells after 48 hrs by sulforhodamine B assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
AID1125076Cytotoxicity against human HeLa cells assessed as inhibition of number of colonies formed in soft agar after 14 days by microscopic analysis2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID476717Growth inhibition of human WiDr cells after 48 hrs by sulforhodamine B assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
AID1125110Inhibition of p53-dependent transcriptional activity in tumor promotion-sensitive mouse JB6 Cl41 cells after 12 hrs by luciferase-based method2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID476713Growth inhibition of human HBL100 cells after 48 hrs by sulforhodamine B assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
AID1392765Antiproliferative activity against human COLO205 cells after 72 hrs by CellTiter-Glo assay2018Bioorganic & medicinal chemistry letters, 06-15, Volume: 28, Issue:11
Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity.
AID1392766Antiproliferative activity against human T47D cells after 72 hrs by CellTiter-Glo assay2018Bioorganic & medicinal chemistry letters, 06-15, Volume: 28, Issue:11
Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity.
AID1392767Antiproliferative activity against human K562 cells after 72 hrs by CellTiter-Glo assay2018Bioorganic & medicinal chemistry letters, 06-15, Volume: 28, Issue:11
Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity.
[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's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's4 (80.00)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: 12.72

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 Index12.72 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.4820hydroxy-1,4-naphthoquinonegeroprotector;
herbicide;
reactive oxygen species generator
lapachol
lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.		2.0510
beta-lapachone
beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.		2.0510benzochromenone;
orthoquinones		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
methylglucoside, (alpha-d)-isomer
methyl alpha-D-glucopyranoside : An alpha-D-glucopyranoside having a methyl substituent at the anomeric position.		2.110alpha-D-glucoside;
methyl D-glucoside
alpha-lapachone
alpha-lapachone: structure in first source		2.0510organic heterotricyclic compound;
organooxygen compound
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		210
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		210
2-methoxyjuglone
2-methoxyjuglone: from Juglan; structure in first source		2.5320
ConditionIndicatedRelationship StrengthStudiesTrials