Compounds > alpha-lapachone
Page last updated: 2024-12-06

alpha-lapachone

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Description

Alpha-lapachone is a naturally occurring naphthoquinone compound found in the bark of the Lapacho tree (Tabebuia impetiginosa). It has been studied extensively for its potential anticancer activity, exhibiting promising effects against various cancer types, including leukemia, melanoma, and lung cancer. Alpha-lapachone targets the enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1), which is overexpressed in many cancer cells. By inhibiting NQO1, alpha-lapachone induces the production of reactive oxygen species (ROS) in cancer cells, leading to their apoptosis. Synthetic methods for alpha-lapachone involve multi-step reactions starting from readily available starting materials, often using Friedel-Crafts acylation and oxidation reactions. Despite its promising preclinical activity, alpha-lapachone faces challenges in clinical development due to its low bioavailability and toxicity. Ongoing research focuses on optimizing its delivery methods and developing analogs with improved pharmacological properties. The compound's unique mechanism of action and its ability to target NQO1 makes it an attractive target for further investigation and development as a potential cancer therapeutic.'

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

Cross-References

ID SourceID
PubMed CID72732
CHEMBL ID441441
CHEBI ID182892
SCHEMBL ID102553
MeSH IDM0371952

Synonyms (40)

Synonym
CHEBI:182892
nsc-629747
alpha-lapachone
.alpha.-lapachone
nsc-26327
2h-naphtho[2,10-dione, 3,4-dihydro-2,2-dimethyl-
NSC26327 ,
lapachone, alpha
4707-33-9
2,2-dimethyl-3,4-dihydro-2h-benzo[g]chromene-5,10-dione
2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
NSC629747 ,
pyranonaphthoquinone derivative, 51
2,2-dimethyl-2h,3h,4h,5h,10h-naphtho[2,3-b]pyran-5,10-dione
bdbm24810
CHEMBL441441
2h-naphtho[2,3-b]pyran-5,10-dione, 3,4-dihydro-2,2-dimethyl-
unii-vpe3aox9qv
lapachoone alpha
alpha lapachone
nsc 26327
2h-naphtho(2,3-b)pyran-5,10-dione, 3,4-dihydro-2,2-dimethyl-
vpe3aox9qv ,
nsc 629747
SCHEMBL102553
lapachone, .alpha.
PJWHOPKRRBUSDH-UHFFFAOYSA-N
2,2-dimethyl-3,4-dihydro-2h-benzo[g]chromene-5,10-dione #
AKOS028108462
CCG-231496
DTXSID00197020
3,4-dihydro-2,2-dimethyl-2h-naphtho[2,3-b]pyran-5,10-dione
E76367
nsc 26327; nsc 629747
Q27291952
MS-23427
CS-0023426
HY-N2848
GLXC-17776
AC-37066
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
organooxygen compoundAn organochalcogen compound containing at least one carbon-oxygen bond.
[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)
Indoleamine 2,3-dioxygenase 1Homo sapiens (human)IC50 (µMol)4.34000.05373.075710.0000AID1798473; AID326467
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
regulation of activated T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell tolerance inductionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of chronic inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of type 2 immune responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
female pregnancyIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic process to kynurenineIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
response to lipopolysaccharideIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of interleukin-10 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of interleukin-12 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
multicellular organismal response to stressIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
kynurenic acid biosynthetic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
swimming behaviorIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
'de novo' NAD biosynthetic process from tryptophanIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
electron transfer activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
heme bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
indoleamine 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
metal ion bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
cytosolIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
smooth muscle contractile fiberIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
stereocilium bundleIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
cytoplasmIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (111)

Assay IDTitleYearJournalArticle
AID379981Cytotoxicity against human multidrug resistant KB-V cells in presence of vinblastine2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1592252Inhibition of Schistosoma mansoni DHODH assessed as remaining enzyme activity at 500 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.
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.
AID1867401Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr1p transporter assessed as fractional inhibitory concentration index incubated for 48 hrs by checkboard assay based microplate reader analysis2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID672965Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as cell death at 50 uM after 72 hrs by propidium iodide staining-based flow cytometric analysis2012Bioorganic & medicinal chemistry, Aug-15, Volume: 20, Issue:16
New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms.
AID380856Antiproliferative activity against human HaCaT cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth.
AID386975Antitrypanosomal activity against Crithidia fasciculata2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Studies of trypanocidal (inhibitory) power of naphthoquinones: evaluation of quantum chemical molecular descriptors for structure-activity relationships.
AID334868Cytotoxicity against human SW626 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID744772Antileishmanial activity against antimony-sensitive Leishmania infantum MCAN/BR/2002/BH400 promastigote infected in Swiss mouse peritoneal macrophages after 72 hrs2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID1867454Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr2p transporter assessed as fractional inhibitory concentration incubated for 48 hrs in presence of lapachone by checkboard assay based microplate re2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID382236Trypanocidal activity against Trypanosoma cruzi Y blood stream trypomastigotes after 24 hrs2008Bioorganic & medicinal chemistry, May-01, Volume: 16, Issue:9
Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones.
AID324607Effect on oxygen uptake per mg of protein in Trypanosoma cruzi Tulahuen epimastigotes relative to control2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.
AID334860Cytotoxicity against mouse P388 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID672220Antiproliferative activity against human LoVo cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID744765Selectivity index, ratio of CC50 for Swiss mouse peritoneal macrophages to IC50 for antimony-sensitive Leishmania amazonensis MHOM/BR/1989/BA199 promastigote2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID1441539Substrate activity at recombinant human NQO1 expressed in Escherichia coli assessed as compound reduction rate by measuring NADPH consumption per umol of enzyme preincubated for 3 mins followed by NADPH addition measured for 5 mins at 2 sec time interval 2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
AID1657060Cytotoxicity against human MCF7 cells assessed as reduction in cell proliferation measured after 72 hrs by WST8 assay2020Bioorganic & medicinal chemistry, 03-15, Volume: 28, Issue:6
STAT3 inhibitory activity of naphthoquinones isolated from Tabebuia avellanedae.
AID324608Effect on oxygen redox cycling in Trypanosoma cruzi Tulahuen assessed as oxygen consumption per mg of protein relative to control2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.
AID379985Cytotoxicity against human SK-N-SH cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID334862Cytotoxicity against human LNCAP cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID665102Growth inhibition of human WiDr cells by SRB assay2012European journal of medicinal chemistry, Jul, Volume: 53β-Lapachone analogs with enhanced antiproliferative activity.
AID1274029Selectivity index, ratio of IC50 for MRC5 cells to IC50 for chloroquine-sensitive NF54 isolated Plasmodium falciparum 3D72016European journal of medicinal chemistry, Jan-27, Volume: 108Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives.
AID334866Cytotoxicity against human Col2 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID1657059Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell proliferation measured after 72 hrs by WST8 assay2020Bioorganic & medicinal chemistry, 03-15, Volume: 28, Issue:6
STAT3 inhibitory activity of naphthoquinones isolated from Tabebuia avellanedae.
AID672223Antiproliferative activity against human Hs683 cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID672225Antiproliferative activity against human U373 cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID672222Antiproliferative activity against human OE21 cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID1867391Antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr1p transporter assessed as reduction in fungal growth incubated for 48 hrs by checkboard assay based microplate reader analysis2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID1858853Cytotoxicity against human LLC-PK1 cells incubated for 24 hrs by MTT assay2021European journal of medicinal chemistry, Jan-15, Volume: 210Antimalarial application of quinones: A recent update.
AID672226Induction of apoptosis in human Jurkat cells assessed as apoptotic cells at 50 uM after 24 hrs using annexin-V/Propidium iodide by flow cytometry2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID1274027Antimalarial activity against chloroquine-sensitive NF54 isolated Plasmodium falciparum 3D7 infected in erythrocytes assessed as inhibition of parasitic growth after 48 hrs by optical microscopy2016European journal of medicinal chemistry, Jan-27, Volume: 108Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives.
AID379979Cytotoxicity against human Col2 cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1858855Antimalarial activity against Plasmodium falciparum W2 incubated for 24 hrs2021European journal of medicinal chemistry, Jan-15, Volume: 210Antimalarial application of quinones: A recent update.
AID1867457Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr2p transporter assessed as reduction in fungal growth incubated for 48 hrs in presence of fluconazole by checkboard assay based microplate reader an2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
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.
AID1858852Cytotoxicity against human A549 cells incubated for 24 hrs by MTT assay2021European journal of medicinal chemistry, Jan-15, Volume: 210Antimalarial application of quinones: A recent update.
AID1356022Antiproliferative activity against human K562 cells measured after 48 hrs by MTT assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells.
AID334863Cytotoxicity against human Lu1 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID334906Growth inhibition of human SW626 cells implanted subcutaneously to NCr nu/nu mouse at 128 to 512 umol/kg, ip administered from day 3 to 6 after implantation measured on day 7 by MTT-based hollow-fiber test2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID672966Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes after 72 hrs by Neubauer counter-based microscopic analysis2012Bioorganic & medicinal chemistry, Aug-15, Volume: 20, Issue:16
New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms.
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.
AID334865Cytotoxicity against human KB cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID672224Antiproliferative activity against human A549 cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID744764Selectivity index, ratio of CC50 for Swiss mouse peritoneal macrophages to IC50 for antimony-resistant Leishmania amazonensis MHOM/BR/1989/BA199 promastigote2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID672221Antiproliferative activity against human SK-MEL-28 cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID1867456Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr1p transporter assessed as reduction in fungal growth incubated for 48 hrs in presence of fluconazole by checkboard assay based microplate reader an2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID324605Growth inhibition of Trypanosoma cruzi Tulahuen epimastigotes assessed as drug level causing decrease in growth constant2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.
AID665100Growth inhibition of human HeLa cells by SRB assay2012European journal of medicinal chemistry, Jul, Volume: 53β-Lapachone analogs with enhanced antiproliferative activity.
AID1597869Selectivity index, ratio of IC50 for mouse J774.A1 cells to MIC for Mycobacterium tuberculosis INH R1 ATCC 35822
AID334905Growth inhibition of human SW626 cells implanted intraperitoneally to NCr nu/nu mouse at 128 to 512 umol/kg, ip administered from day 3 to 6 after implantation measured on day 7 by MTT-based hollow-fiber test2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID744771Antileishmanial activity against antimony-resistant Leishmania infantum MCAN/BR/2002/BH400 promastigote infected in Swiss mouse peritoneal macrophages after 72 hrs2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID744766Selectivity index, ratio of CC50 for Swiss mouse peritoneal macrophages to IC50 for antimony-resistant Leishmania infantum MCAN/BR/2002/BH400 promastigote2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID1867392Antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr2p transporter assessed as reduction in fungal growth incubated for 48 hrs by checkboard assay based microplate reader analysis2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID1597872Selectivity index, ratio of IC50 for mouse J774.A1 cells to MIC for Mycobacterium tuberculosis H37Rv
AID380857Cytotoxicity against human HaCaT cells assessed as LDH release at 2 uM1999Journal of natural products, Aug, Volume: 62, Issue:8
Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth.
AID744768Cytotoxicity against Swiss mouse peritoneal macrophages after 24 hrs by MTT assay2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID334864Cytotoxicity against human KBV1 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID334867Cytotoxicity against human BC1 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID1858851Cytotoxicity against human HepG2 cells incubated for 24 hrs by MTT assay2021European journal of medicinal chemistry, Jan-15, Volume: 210Antimalarial application of quinones: A recent update.
AID1441541Selectivity ratio of compound reduction rate catalyzed by recombinant human NQO1 expressed in Escherichia coli to compound reduction rate catalyzed by recombinant human CPR expressed in baculovirus infected insect cells2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
AID1657056Inhibition of IL-6 induced STAT3 phosphorylation at Tyr705 residue in human MCF7 cells at 1 uM preincubated for 1 hr followed by IL-6 stimulation and measured after 1 hr by Western blot analysis relative to control2020Bioorganic & medicinal chemistry, 03-15, Volume: 28, Issue:6
STAT3 inhibitory activity of naphthoquinones isolated from Tabebuia avellanedae.
AID1441540Substrate activity at recombinant human CPR expressed in baculovirus infected insect cells assessed as compound reduction rate by measuring NADPH consumption per umol of enzyme preincubated for 3 mins followed by NADPH addition measured for 5 mins at 2 se2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
AID1597874Antimycobacterial activity against isoniazid resistant Mycobacterium tuberculosis ATCC 35822 after 7 days by resazurin microtiter assay
AID386972Oxidation of dithiothreitol assessed as oxygen consumption at 50 uM2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Studies of trypanocidal (inhibitory) power of naphthoquinones: evaluation of quantum chemical molecular descriptors for structure-activity relationships.
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.
AID1867451Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr2p transporter assessed as reduction in fungal growth incubated for 48 hrs in presence of lapachone by checkboard assay based microplate reader anal2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID379980Cytotoxicity against human KB cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1597870Selectivity index, ratio of IC50 for mouse J774.A1 cells to MIC for Mycobacterium tuberculosis INH R2
AID379978Cytotoxicity against human Lo1 cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1867459Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr1p transporter assessed as fractional inhibitory concentration in presence of fluconazole incubated for 48 hrs by checkboard assay based microplate 2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID379986Cytotoxicity against human M109 cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1274028Cytotoxicity against human MRC5 cells assessed as cell growth inhibition after 48 hrs by alamar blue assay2016European journal of medicinal chemistry, Jan-27, Volume: 108Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives.
AID672967Cytotoxicity against african green monkey Vero cells after 72 hrs by spectrophotometric analysis2012Bioorganic & medicinal chemistry, Aug-15, Volume: 20, Issue:16
New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms.
AID379977Cytotoxicity against human BC1 cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1597873Antimycobacterial activity against isoniazid resistant Mycobacterium tuberculosis H37Rv ATCC 27294 measured after 7 days by resazurin microtiter assay
AID672229Antiproliferative activity against human MCF7/AZ cells assessed as reduction in cell viability after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID672227Antiproliferative activity against human Jurkat cells assessed as reduction in cell viability after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID1657061Cytotoxicity against human A549 cells assessed as reduction in cell proliferation measured after 72 hrs by WST8 assay2020Bioorganic & medicinal chemistry, 03-15, Volume: 28, Issue:6
STAT3 inhibitory activity of naphthoquinones isolated from Tabebuia avellanedae.
AID672219Antiproliferative activity against human PC3 cells assessed as reduction in cell viability after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID744769Antileishmanial activity against antimony-resistant Leishmania amazonensis MHOM/BR/1989/BA199 promastigote infected in Swiss mouse peritoneal macrophages after 72 hrs2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID379984Cytotoxicity against human SW626 cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1867453Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr1p transporter assessed as fractional inhibitory concentration incubated for 48 hrs in presence of lapachone by checkboard assay based microplate re2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID665099Growth inhibition of human HBL100 cells by SRB assay2012European journal of medicinal chemistry, Jul, Volume: 53β-Lapachone analogs with enhanced antiproliferative activity.
AID326467Inhibition of purified human recombinant IDO2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.
AID324609Antitrypanosomal activity against Trypanosoma cruzi Tulahuen assessed as trypomastigote viability at 0.21 uM by MTT assay relative to control2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.
AID1597875Antimycobacterial activity against isoniazid resistant Mycobacterium tuberculosis measured after 7 days by resazurin microtiter assay
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.
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.
AID386974Antitrypanosomal activity against Leptomonas seymouri2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Studies of trypanocidal (inhibitory) power of naphthoquinones: evaluation of quantum chemical molecular descriptors for structure-activity relationships.
AID1657057Inhibition of IL-6 induced STAT3 phosphorylation at Tyr705 residue in human MCF7 cells at 10 uM preincubated for 1 hr followed by IL-6 stimulation and measured after 1 hr by Western blot analysis relative to control2020Bioorganic & medicinal chemistry, 03-15, Volume: 28, Issue:6
STAT3 inhibitory activity of naphthoquinones isolated from Tabebuia avellanedae.
AID334861Cytotoxicity against human MCF7 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID744767Selectivity index, ratio of CC50 for Swiss mouse peritoneal macrophages to IC50 for antimony-sensitive Leishmania infantum MCAN/BR/2002/BH400 promastigote2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID735529Cytotoxicity against human WHCO1 cells after 24 hrs by MTT assay2013European journal of medicinal chemistry, Apr, Volume: 62Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells.
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.
AID379982Cytotoxicity against human multidrug resistant KB-V cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1597871Cytotoxicity against mouse J774.A1 cells measured after 24 hrs by resazurin based assay
AID1867450Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr1p transporter assessed as reduction in fungal growth incubated for 48 hrs in presence of lapachone by checkboard assay based microplate reader anal2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID379983Cytotoxicity against human LNCaP cells2000Journal of natural products, Apr, Volume: 63, Issue:4
Cytotoxic constituents of the roots of Ekmanianthe longiflora.
AID1858854Cytotoxicity against human MRC5 cells incubated for 24 hrs by MTT assay2021European journal of medicinal chemistry, Jan-15, Volume: 210Antimalarial application of quinones: A recent update.
AID672228Antiproliferative activity against human HeLa cells assessed as reduction in cell viability after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.
AID1867402Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr2p transporter assessed as fractional inhibitory concentration index incubated for 48 hrs by checkboard assay based microplate reader analysis2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID1867460Indifferent antifungal activity against fluconazole resistant Saccharomyces cerevisiae overexpressing CgCdr2p transporter assessed as fractional inhibitory concentration in presence of fluconazole incubated for 48 hrs by checkboard assay based microplate 2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Effects of β-lapachone and β-nor-lapachone on multidrug efflux transporters and biofilms of Candida glabrata.
AID665101Growth inhibition of human SW1573 cells by SRB assay2012European journal of medicinal chemistry, Jul, Volume: 53β-Lapachone analogs with enhanced antiproliferative activity.
AID335168Toxicity in NCr nu/nu mouse subcutaneously implanted with human SW626 cells assessed as body weight change at 128 to 512 umol/kg, ip administered from day 3 to 6 after implantation measured on day 72002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID386973Oxidation of dihydrolipoamide assessed as oxygen consumption at 50 uM2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Studies of trypanocidal (inhibitory) power of naphthoquinones: evaluation of quantum chemical molecular descriptors for structure-activity relationships.
AID744770Antileishmanial activity against antimony-sensitive Leishmania amazonensis MHOM/BR/1989/BA199 promastigote infected in Swiss mouse peritoneal macrophages after 72 hrs2013European journal of medicinal chemistry, May, Volume: 63Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.
AID1441542Electrochemical behavior of the compound assessed as electrochemical redox potential with reference to ferrocene at 1 mM using Ag/AgCl reference electrode measured up to -2 V at potential sweep rates of 50 mV/s by cyclic voltammetry2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
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.
AID334859Cytotoxicity against human SK-MEL-2 cells after 72 hrs by SRB assay2002Journal of natural products, Jun, Volume: 65, Issue:6
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests.
AID1356021Antiproliferative activity against human MDA-MB-231 cells measured after 48 hrs by MTT assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells.
AID1798473Enzyme Inhibition Assay from Article 10.1021/jm7014155: \\Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.\\2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.27)18.2507
2000's17 (38.64)29.6817
2010's21 (47.73)24.3611
2020's5 (11.36)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.50

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

MetricThis Compound (vs All)
Research Demand Index16.50 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (8.89%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (91.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		2.1310halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
mercaptoethanol
Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.		210alkanethiol;
primary alcohol		geroprotector
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.		210anthracenesantipsoriatic
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		3.4110aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
fluconazole
Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.		2.4110conazole antifungal drug;
difluorobenzene;
tertiary alcohol;
triazole antifungal drug		environmental contaminant;
P450 inhibitor;
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.		2.4520hydroxy-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.		10.7140
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.		6.28260benzochromenone;
orthoquinones		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
vitamin k 3
Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.		2.04101,4-naphthoquinones;
vitamin K		angiogenesis inhibitor;
antineoplastic agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
human urinary metabolite;
nutraceutical
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).		2.49201,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.0510mitomycinalkylating agent;
antineoplastic agent
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		2.0610amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.1110aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
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.		2.4920
dichlorodicyanobenzoquinone
dichlorodicyanobenzoquinone: request from searcher		2.1310
dichlone
dichlone: structure		2.7730
chloranil
Chloranil: A quinone fungicide used for treatment of seeds and foliage.. tetrachloro-1,4-benzoquinone : A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.		2.13101,4-benzoquinones;
organochlorine compound		EC 2.7.1.33 (pantothenate kinase) inhibitor;
metabolite
1,4-naphthoquinone
naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.		7.45201,4-naphthoquinones
phenylbenzoquinone
phenylbenzoquinone: RN given refers to parent cpd		2.0410
eleutherin
eleutherin: InChIKey: IAJIIJBMBCZPSW-DTWKUNHWSA-N		210benzoisochromanequinone;
p-quinones
thymoquinone
thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.		3.41101,4-benzoquinonesadjuvant;
anti-inflammatory agent;
antidepressant;
antineoplastic agent;
antioxidant;
cardioprotective agent;
plant metabolite
4-chromone
4-chromone: structure given in first source. chromone : The simplest member of the class of chromones that is 4H-chromene with an oxo group at position 4.		2.0410chromones;
enone
1,2-naphthoquinone
naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.		2.47201,2-naphthoquinonesaryl hydrocarbon receptor agonist;
carcinogenic agent
gentian violet
Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.		2.0410organic chloride saltanthelminthic drug;
antibacterial agent;
antifungal agent;
antiseptic drug;
histological dye
2-methyl-1,4-benzoquinone
cresoquinone: no further information available 6/2003		2.4920
2-chloro-1,4-naphthoquinone
2-chloro-1,4-naphthoquinone: Vitamin K dependent carboxylase antagonist		2.21101,4-naphthoquinones;
organochlorine compound
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.		2.77301,4-naphthoquinones;
enol ether		antimicrobial agent;
metabolite;
plant metabolite
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
2-hydroxyjuglone
2-hydroxyjuglone: structure in first source		2.0510
mansonone c
mansonone C: structure in first source		2.04101,2-naphthoquinones;
sesquiterpenoid
ferric chloride
ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents		2.1310iron coordination entityastringent;
Lewis acid
benzonidazole
benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.		2.7430C-nitro compound;
imidazoles;
monocarboxylic acid amide		antiprotozoal drug
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		2.0810pseudohalide anionmitochondrial respiratory-chain inhibitor
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).		2.0110taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
etoposide
[no description available]		210beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
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
chloroquine diphosphate
[no description available]		2.1310
rufigallol
rufigallol: structure given in first source		3.4110hexahydroxyanthraquinone
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.08101,2,3-triazole
xyloidone
[no description available]		2.9640
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.		3.7620hydroxy-1,2-naphthoquinone
hydrolapachol
hydrolapachol: inhibits mitochondrial respiratory chain		2.4920
naphtho(2,3-b)furan-4,9-dione
naphtho(2,3-b)furan-4,9-dione: structure given in first source		2.1710
mansonone e
mansonone E: a potent anti-bacterial sesquiterpenoid isolated from the dried root bark of Ulmus pumila; structure in first source		2.0410
mansonone f
mansonone F: a potent anti-bacterial sesquiterpenoid; structure in first source		2.0410
diosgenin
[no description available]		2.01103beta-sterol;
hexacyclic triterpenoid;
sapogenin;
spiroketal		antineoplastic agent;
antiviral agent;
apoptosis inducer;
metabolite
dioscin
[no description available]		2.0110hexacyclic triterpenoid;
spiroketal;
spirostanyl glycoside;
trisaccharide derivative		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 1.14.18.1 (tyrosinase) inhibitor;
hepatoprotective agent;
metabolite
e 64
E 64: cysteine protease inhibitor of microbial origin, which inhibits cathepsin B (EC 3.4.22.1) and cathepsin L (EC 3.4.22.-)		2.0610dicarboxylic acid monoamide;
epoxy monocarboxylic acid;
guanidines;
L-leucine derivative;
zwitterion		antimalarial;
antiparasitic agent;
protease inhibitor
singlet oxygen
Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.		2.0410chalcogen;
monoatomic oxygen;
nonmetal atom		macronutrient
norlapachol
norlapachol: structure in first source		2.7430
dunnione
dunnione: RN given for (+)-isomer; an industrial fungicide; structure in first source		2.1510naphthofuran
diospyrin
diospyrin: structure given in first source		3.4110hydroxy-1,4-naphthoquinone;
ring assembly
ochraceolide a
ochraceolide A: structure given in first source; isolated from Kokoona ochracea stem bark		2.0110
knipholone
knipholone: a binary compound of the anthraquinone chrysophanol and an acetylphloroglucinol. knipholone : An anthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 4 and 6, a methyl group at position 2 and a 3-acetyl-2,6-dihydroxy-4-methoxyphenyl group at position 1. It exhibits antioxidant, cytotoxic and antiplasmodial activities.		3.4110aromatic ketone;
dihydroxyanthraquinone;
methoxybenzenes;
methyl ketone;
polyphenol;
resorcinols		antineoplastic agent;
antioxidant;
antiplasmodial drug;
leukotriene antagonist;
metabolite
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		11.27260
nor-beta-lapachone
nor-beta-lapachone: has antineoplastic activity; structure in first source		3.0540
vitamin k 1
Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.		2.0410phylloquinones;
vitamin K		cofactor;
human metabolite;
plant metabolite
geldanamycin
[no description available]		3.41101,4-benzoquinones;
ansamycin;
carbamate ester;
organic heterobicyclic compound		antimicrobial agent;
antineoplastic agent;
antiviral agent;
cysteine protease inhibitor;
Hsp90 inhibitor
antimony
Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.		2.0810metalloid atom;
pnictogen
nifurtimox
Nifurtimox: A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.		2.0410nitrofuran antibiotic
artesunate
artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether		3.4110artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer
1-oxomiltirone
1-oxomiltirone: from roots of the Iranian medicinal plant Perovskia abrotanoides; structure in first source		3.4110
2-methylnaphtho(2,3-b)furan-4,9-dione
[no description available]		3.4110
2-acetylfuranonaphthoquinone
2-acetylfuranonaphthoquinone: has antineoplastic activity; structure in first source		2.9640
baricitinib
[no description available]		2.2510azetidines;
nitrile;
pyrazoles;
pyrrolopyrimidine;
sulfonamide		anti-inflammatory agent;
antirheumatic drug;
antiviral agent;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
immunosuppressive agent
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.4110ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
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
antipain
Antipain: An oligopeptide produced by various bacteria which acts as a protease inhibitor.		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Palmoplantaris Pustulosis
[description not available]		0210
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.		0210
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		02.4120
Cancer of Colon
[description not available]		02.0110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.4320
Malignant Melanoma
[description not available]		02.0110
Cancer of Ovary
[description not available]		02.0110
Cancer of Prostate
[description not available]		02.0110
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0110
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.0110
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.0110
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0110
Cancer of Esophagus
[description not available]		02.0810
Esophageal Neoplasms
Tumors or cancer of the ESOPHAGUS.		02.0810
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
Plasmodium falciparum Malaria
[description not available]		03.2310
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		03.2310
Leishmania Infection
[description not available]		02.610
Leishmaniasis
A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).		02.610
Leucocythaemia
[description not available]		02.5220
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.5220
Benign Neoplasms
[description not available]		03.0610
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.0610
Leishmaniasis, American
[description not available]		02.1110
Leishmaniasis, Cutaneous
An endemic disease that is characterized by the development of single or multiple localized lesions on exposed areas of skin that typically ulcerate. The disease has been divided into Old and New World forms. Old World leishmaniasis is separated into three distinct types according to epidemiology and clinical manifestations and is caused by species of the L. tropica and L. aethiopica complexes as well as by species of the L. major genus. New World leishmaniasis, also called American leishmaniasis, occurs in South and Central America and is caused by species of the L. mexicana or L. braziliensis complexes.		02.1110
American Trypanosomiasis
[description not available]		02.9810
Chagas Disease
Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.		02.9810