Compounds > hydrolapachol
Page last updated: 2024-11-06

hydrolapachol

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

Description

hydrolapachol: inhibits mitochondrial respiratory chain [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID76864
CHEMBL ID155771
MeSH IDM0051480

Synonyms (21)

Synonym
4-hydroxy-3-(3-methylbutyl)naphthalene-1,2-dione
2-hydroxy-3-(3-methyl-butyl)-naphthalene-1,4-dione
2-hydroxy-3-(3-methylbutyl)-1,4-naphthoquinone
1,4-naphthoquinone, 2-hydroxy-3-isopentyl-
nsc 26695
1,4-naphthalenedione, 2-hydroxy-3-(3-methylbutyl)-
2-hydroxy-3-isopentyl-naphthalene-1,4-dione
nsc26695
hydrolapachol
1, 2-hydroxy-3-isopentyl-
1, 2-hydroxy-3-(3-methylbutyl)-
3343-38-2
nsc-26695
CHEMBL155771 ,
2-hydroxy-3-isopentylnaphthoquinone #
CBIBTBSDPZSTOE-UHFFFAOYSA-N
4-hydroxy-3-isopentylnaphthalene-1,2-dione
2-hydroxy-3-isopentylnaphthalene-1,4-dione
2-hydroxy-3-(3-methylbutyl)naphthalene-1,4-dione
DTXSID40955060
bdbm50523217
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase Schistosoma mansoniIC50 (µMol)0.02300.01901.94088.8000AID1592257
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)IC50 (µMol)0.70900.00050.742710.0000AID1592258
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
UDP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' UMP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
pyrimidine ribonucleotide biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' pyrimidine nucleobase biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
dihydroorotase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
protein bindingDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase (quinone) activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrionDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
cytosolDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1592256Inhibition of Schistosoma mansoni DHODH assessed as remaining enzyme activity at 125 uM using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay relative to control2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID1592263Non-competitive inhibition of human DHODH using DHO as substrate measured at 4 secs interval for 60 secs by Lineweaver-Burk plot analysis2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID618758Antitubercular activity against Mycobacterium tuberculosis H37Rv after 9 days by resazurin reduction assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Quinonoid and phenazine compounds: synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis.
AID277224Partition coefficient, log P of the compound2007Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4
Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line.
AID158505Antimalarial activity against Plasmodium berghei; Active1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Structure-activity analyzed by pattern recognition: the asymmetric case.
AID1592261Non-competitive inhibition of Schistosoma mansoni DHODH using DHO as substrate measured at 4 secs interval for 60 secs by Lineweaver-Burk plot analysis2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID1592258Inhibition of human DHODH using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID277223Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay2007Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4
Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line.
AID567495Cytotoxicity against human MDA-MB-435 cells after 72 hrs by MTT assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Synthesis and evaluation of quinonoid compounds against tumor cell lines.
AID567497Cytotoxicity against human SF295 cells after 72 hrs by MTT assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Synthesis and evaluation of quinonoid compounds against tumor cell lines.
AID567493Cytotoxicity against human PBMC cells after 72 hrs by Alamar Blue assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Synthesis and evaluation of quinonoid compounds against tumor cell lines.
AID1592259Selectivity Index, ratio of IC50 for human DHODH to IC50 for Schistosoma mansoni DHODH2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID1592257Inhibition of Schistosoma mansoni DHODH using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID618761Cytotoxicity against human PBMC after 72 hrs by Alamar blue assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Quinonoid and phenazine compounds: synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis.
AID618759Antitubercular activity against rifampicin-resistant Mycobacterium tuberculosis ATCC 35338 harboring His-526-Tri mutation in rpoB gene after 9 days by resazurin reduction assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Quinonoid and phenazine compounds: synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis.
AID567494Cytotoxicity against human HL60 cells after 72 hrs by MTT assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Synthesis and evaluation of quinonoid compounds against tumor cell lines.
AID23447Partition coefficient (logP)1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Structure-activity analyzed by pattern recognition: the asymmetric case.
AID618760Antitubercular activity against isoniazid-resistant Mycobacterium tuberculosis ATCC 35822 harboring Ser-315-Tri mutation in katG gene after 9 days by resazurin reduction assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Quinonoid and phenazine compounds: synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis.
AID567496Cytotoxicity against human HCT8 cells after 72 hrs by MTT assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Synthesis and evaluation of quinonoid compounds against tumor cell lines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (16.67)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's3 (50.00)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: 12.52

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 Index12.52 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.52)

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
embelin
embelin: from Embelia fruit (Myrsinaceae). embelin : A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease.		1.9510dihydroxy-1,4-benzoquinonesantimicrobial agent;
antineoplastic agent;
hepatitis C protease inhibitor;
plant metabolite
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.0610carbohydrazideantitubercular agent;
drug allergen
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.		2.7730
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.		2.4520benzochromenone;
orthoquinones		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
quinone
benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).		2.21101,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
lawsone
lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.		2.2110
phthiocol
phthiocol: antihemorrhagic antibiotic isolated from Mycobacterium tuberculosis; structure		1.9510
2-methyl-1,4-benzoquinone
cresoquinone: no further information available 6/2003		2.2110
2-chloro-1,4-naphthoquinone
2-chloro-1,4-naphthoquinone: Vitamin K dependent carboxylase antagonist		2.21101,4-naphthoquinones;
organochlorine compound
2,5-di-tert-butylbenzoquinone
[no description available]		2.2110benzoquinones;
p-quinones
2-tert-butyl-4-quinone
2-tert-butyl-4-quinone: a metabolite of butylated hydroxyanisole ; structure given in first source		2.2110
menoctone
[no description available]		1.9510
brequinar
brequinar : A quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties.		2.2110biphenyls;
monocarboxylic acid;
monofluorobenzenes;
quinolinemonocarboxylic acid		anticoronaviral agent;
antimetabolite;
antineoplastic agent;
antiviral agent;
EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor;
immunosuppressive agent;
pyrimidine synthesis inhibitor
alpha-lapachone
alpha-lapachone: structure in first source		2.4920organic heterotricyclic compound;
organooxygen compound
atovaquone
Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.		2.2110hydroxy-1,2-naphthoquinone
resorufin galactopyranoside
resorufin galactopyranoside: fluorogenic substrate for beta-galactosidase activity		2.0410
norlapachol
norlapachol: structure in first source		2.4520
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		2.0410
nor-beta-lapachone
nor-beta-lapachone: has antineoplastic activity; structure in first source		2.0610
teriflunomide
[no description available]		2.2110(trifluoromethyl)benzenes;
aromatic amide;
enamide;
enol;
nitrile;
secondary carboxamide		drug metabolite;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
hepatotoxic agent;
non-steroidal anti-inflammatory drug;
tyrosine kinase inhibitor
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.0610cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Schistosoma mansoni Infection
[description not available]		02.2110
Schistosomiasis mansoni
Schistosomiasis caused by Schistosoma mansoni. It is endemic in Africa, the Middle East, South America, and the Caribbean and affects mainly the bowel, spleen, and liver.		02.2110