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lapachol
1,4-naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)- (9CI)

Supplier Sponsors

CAS Number: 84-79-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-563-7
FDA UNII: B221938VB6
Nikkaji Web:J4.900J
Beilstein Number:2051889
MDL:MFCD00001679
XlogP3-AA:2.80 (est)
Molecular Weight:242.27418000
Formula:C15 H14 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 139.50 °C. @ 760.00 mm Hg
Boiling Point: 398.57 °C. @ 760.00 mm Hg (est)
Flash Point: 408.00 °F. TCC ( 209.00 °C. ) (est)
logP (o/w): 2.516 (est)
Soluble in:
 water, 55.6 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Lapachol 98%
BOC Sciences
For experimental / research use only.
Lapachol > 95%
Odor: characteristic
Use: a reagent used in the synthesis of B-Lapachones for use in anti-proliferative tumor studies.
ExtraSynthese
For experimental / research use only.
Lapachol (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Lapachol 98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Lapachol 98%
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 400 mg/kg
Journal of Medicinal Chemistry. Vol. 26, Pg. 570, 1983.

oral-mouse LD50 487 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Toxicology and Applied Pharmacology. Vol. 17, Pg. 1, 1970.

oral-rat LDLo 1200 mg/kg
Toxicology and Applied Pharmacology. Vol. 17, Pg. 1, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for lapachol usage levels up to:
 not for fragrance use.
 
Recommendation for lapachol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3884
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
Chemidplus:0000084797
RTECS:QL8750000 for cas# 84-79-7
 
References:
 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):3884
Pubchem (sid):134972504
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C10366
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2914.69.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 bethabarra wood
 c.i. 75490
 C.I. natural yellow 16
 greenharten
 greenhartin
2-hydroxy-3-(3-methyl but-2-enyl)-1,4-naphthoquinone
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
 IPE-tobacco wood
 lapachic acid
 lapachol wood
1,4-naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)- (9CI)
1,4-naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-
 surinam greenheart wood
 taigu wood
 taiguic acid
 tecomin
 zlut prirodni 16
 

Articles:

PubMed:Blood shizonticidal activities of phenazines and naphthoquinoidal compounds against Plasmodium falciparum in vitro and in mice malaria studies.
PubMed:Determination of the depth profile distribution of guest species in microporous materials using the voltammetry of immobilized particles methodology: application to lapachol attachment to palygorskite and kaolinite.
PubMed:Vasorelaxation induced by a new naphthoquinone-oxime is mediated by NO-sGC-cGMP pathway.
PubMed:Selective modulation of plasmodial Hsp70s by small molecules with antimalarial activity.
PubMed:The pterocarpanquinone LQB-118 inhibits tumor cell proliferation by downregulation of c-Myc and cyclins D1 and B1 mRNA and upregulation of p21 cell cycle inhibitor expression.
PubMed:Isolation and identification of α-glucosidase and protein glycation inhibitors from Stereospermum colais.
PubMed:Antiparasitic activities of novel ruthenium/lapachol complexes.
PubMed:Chemical markers of occupational exposure to teak wood dust.
PubMed:Cytotoxicity of lapachol metabolites produced by probiotics.
PubMed:Selective binding of naphthoquinone derivatives to serum albumin proteins and their effects on cytotoxicity.
PubMed:1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.
PubMed:Electrochemical analysis in a liposome suspension using lapachol as a hydrophobic electro active species.
PubMed:Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives.
PubMed:Isolation of major components from the roots of Godmania aesculifolia and determination of their antifungal activities.
PubMed:Structural elucidation of the metabolites of lapachol in rats by liquid chromatography-tandem mass spectrometry.
PubMed:Beyond topoisomerase inhibition: antitumor 1,4-naphthoquinones as potential inhibitors of human monoamine oxidase.
PubMed:Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: electrochemical studies on the effects of the quinoidal moiety.
PubMed:β-Lapachone activity in synergy with conventional antimicrobials against methicillin resistant Staphylococcus aureus strains.
PubMed:Diterpenylquinone hybrids: synthesis and assessment of gastroprotective mechanisms of action in human cells.
PubMed:Anti-diabetic activity of active fractions of Stereospermum tetragonum DC and isolation of active principles.
PubMed:Cytotoxicity and In Vitro Antileishmanial Activity of Antimony (V), Bismuth (V), and Tin (IV) Complexes of Lapachol.
PubMed:The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives.
PubMed:A conserved lysine residue controls iron-sulfur cluster redox chemistry in Escherichia coli fumarate reductase.
PubMed:Organometallic anticancer complexes of lapachol: metal centre-dependent formation of reactive oxygen species and correlation with cytotoxicity.
PubMed:Electronic structure and gas-phase chemistry of protonated α- and β-quinonoid compounds: a mass spectrometry and computational study.
PubMed:Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells.
PubMed:Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: a computational and mass spectrometry study of lapachol congeners.
PubMed:Addition of thiols to o-quinone methide: new 2-hydroxy-3-phenylsulfanylmethyl[1,4]naphthoquinones and their activity against the human malaria parasite Plasmodium falciparum (3D7).
PubMed:A mechanistic study on the Hooker oxidation: synthesis of novel indane carboxylic acid derivatives from lapachol.
PubMed:From body art to anticancer activities: perspectives on medicinal properties of henna.
PubMed:Potential gastroprotective effect of novel cyperenoic acid/quinone derivatives in human cell cultures.
PubMed:Quinones derived from plant secondary metabolites as anti-cancer agents.
PubMed:Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds.
PubMed:A proteomic insight into the effects of the immunomodulatory hydroxynaphthoquinone lapachol on activated macrophages.
PubMed:Determination of lapachol in the presence of other naphthoquinones using 3MPA-CdTe quantum dots fluorescent probe.
PubMed:β-Lapachone analogs with enhanced antiproliferative activity.
PubMed:Lapacho tea (Tabebuia impetiginosa) extract inhibits pancreatic lipase and delays postprandial triglyceride increase in rats.
PubMed:Lapachol as an epithelial tumor inhibitor agent in Drosophila melanogaster heterozygote for tumor suppressor gene wts.
PubMed:A new type of pterocarpanquinone that affects Toxoplasma gondii tachyzoites in vitro.
PubMed:Antimony(V) and bismuth(V) complexes of lapachol: synthesis, crystal structure and cytotoxic activity.
PubMed:Synthesis and pharmacological activity of diterpenylnaphthoquinone derivatives.
PubMed:Coordination of lapachol to bismuth(III) improves its anti-inflammatory and anti-angiogenic activities.
PubMed:Genotoxicity of lapachol evaluated by wing spot test of Drosophila melanogaster.
PubMed:Lapachol suppresses cell proliferation and secretion of interleukin-6 and plasminogen activator inhibitor-1 of fibroblasts derived from hypertrophic scars.
PubMed:β-lapachone accelerates the recovery of burn-wound skin.
PubMed:Screening for small molecule modulators of Hsp70 chaperone activity using protein aggregation suppression assays: inhibition of the plasmodial chaperone PfHsp70-1.
PubMed:Natural products as starting points for future anti-malarial therapies: going back to our roots?
PubMed:Synthetic lapachol derivatives relax guinea-pig ileum by blockade of the voltage-gated calcium channels.
PubMed:Natural and synthetic naphthoquinones active against Trypanosoma cruzi: an initial step towards new drugs for Chagas disease.
PubMed:The hydroxy-naphthoquinone lapachol arrests mycobacterial growth and immunomodulates host macrophages.
PubMed:Combination of chiroptical, absorption and fluorescence spectroscopic methods reveals multiple, hydrophobicity-driven human serum albumin binding of the antimalarial atovaquone and related hydroxynaphthoquinone compounds.
PubMed:Fragmentation studies and electrospray ionization mass spectrometry of lapachol: protonated, deprotonated and cationized species.
PubMed:LQB-118, a pterocarpanquinone structurally related to lapachol [2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone]: a novel class of agent with high apoptotic effect in chronic myeloid leukemia cells.
PubMed:Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
PubMed:1,4-Naphthoquinones as inducers of oxidative damage and stress signaling in HaCaT human keratinocytes.
PubMed:Lapachol induces clastogenic effects in rats.
PubMed:Acanthamoeba castellanii Neff: In vitro activity against the trophozoite stage of a natural sesquiterpene and a synthetic cobalt(II)-lapachol complex.
PubMed:1,2-Dihydr-oxy-2-(3-methyl-but-2-en-yl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid monohydrate.
PubMed:Effect of hydroxy substituent on the prooxidant action of naphthoquinone compounds.
PubMed:The trypanocidal activity of naphthoquinones: a review.
PubMed:LC-APCI mass spectrometric method development and validation for the determination of atovaquone in human plasma.
PubMed:Modulatory effects of Tabebuia impetiginosa (Lamiales, Bignoniaceae) on doxorubicin-induced somatic mutation and recombination in Drosophila melanogaster.
PubMed:Crystal and molecular structure of manganese(II) lapacholate, a novel polymeric species undergoing temperature-reversible metal to ligand electron transfer.
PubMed:Comparison of the cytotoxic effect of lapachol, alpha-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells.
PubMed:Toxicological assessment of beta-lapachone on organs from pregnant and non-pregnant rats.
PubMed:Dolichandroside A, a new alpha-glucosidase inhibitor and DPPH free-radical scavenger from Dolichandrone falcata seem.
PubMed:Red Lapacho (Tabebuia impetiginosa)--a global ethnopharmacological commodity?
PubMed:Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.
PubMed:Antitumor activity of two derivatives from 2-acylamine-1, 4-naphthoquinone in mice bearing S180 tumor.
PubMed:Antitumoral activity of new polyamine-naphthoquinone conjugates.
PubMed:Development of lapachol topical formulation: anti-inflammatory study of a selected formulation.
PubMed:Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones.
PubMed:Promotion or suppression of experimental metastasis of B16 melanoma cells after oral administration of lapachol.
PubMed:Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.
PubMed:Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis.
PubMed:Cytotoxic and DNA-topoisomerase effects of lapachol amine derivatives and interactions with DNA.
PubMed:Quinones from plants of northeastern Brazil: structural diversity, chemical transformations, NMR data and biological activities.
PubMed:Reproductive toxicity of lapachol in adult male Wistar rats submitted to short-term treatment.
PubMed:Applications of counter-current chromatography in organic synthesis purification of heterocyclic derivatives of lapachol.
PubMed:Antifungal chemical compounds identified using a C. elegans pathogenicity assay.
PubMed:Novel rearranged abietane diterpenoids from the roots of Salvia sahendica.
PubMed:Antiplasmodial activity of naphthoquinones related to lapachol and beta-lapachone.
PubMed:Constituents of the root wood of Austroplenckia populnea var. ovata.
PubMed:Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis.
PubMed:Synthesis of naphthofuranquinones with activity against Trypanosoma cruzi.
PubMed:Microwave-assisted rapid cyclization of lapachol, a main constituent of Heterophragma adenophyllum.
PubMed:Newbouldiaquinone A: A naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis.
PubMed:Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori.
PubMed:Synthesis of 3-aryl-5-decapentyl-1,2,4-oxadiazoles possessing antiinflammatory and antitumor properties.
PubMed:Larvicidal activity of Cybistax antisyphilitica against Aedes aegypti larvae.
PubMed:New 1,2,3,4-tetrahydro-1-aza-anthraquinones and 2-aminoalkyl compounds from norlapachol with molluscicidal activity.
PubMed:Acrosome reaction in bovine spermatozoa: role of reactive oxygen species and lactate dehydrogenase C4.
PubMed:Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis.
PubMed:Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria.
PubMed:Cytotoxic pyranonaphthoquinones from Melloa quadrival vis (Bignoniaceae).
PubMed:Antileishmanial activity of lapachol analogues.
PubMed:Demonstration of the lapachol as a potential drug for reducing cancer metastasis.
PubMed:Molluscicidal activity of synthetic lapachol amino and hydrogenated derivatives.
PubMed:Photoreactions of 1,4-Naphthoquinones: effects of substituents and water on the intermediates and reactivity.
PubMed:NO reductase from Bacillus azotoformans is a bifunctional enzyme accepting electrons from menaquinol and a specific endogenous membrane-bound cytochrome c551.
PubMed:Isolation of colour components from native dye-bearing plants in northeastern India.
PubMed:Antimalarial activity of phenazines from lapachol, beta-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo.
PubMed:Glutamate 87 is important for menaquinol binding in DmsC of the DMSO reductase (DmsABC) from Escherichia coli.
PubMed:Monoarylhydrazones of alpha-lapachone: synthesis, chemical properties and antineoplastic activity.
PubMed:Naphthoquinone derivatives and lignans from the Paraguayan crude drug "tayï pytá" (Tabebuia heptaphylla, Bignoniaceae).
PubMed:Electrochemical study of oxygen interaction with lapachol and its radical anions.
PubMed:Inhibitory effects of lapachol derivatives on epstein-barr virus activation.
PubMed:Fetal growth in rats treated with lapachol.
PubMed:The anatomy and chemistry of the colour bands of grasstree stems (Xanthorrhoea preissii) used for plant age and fire history determination.
PubMed:New enamine derivatives of lapachol and biological activity.
PubMed:Toxicity of lapachol and isolapachol and their potassium salts against Biomphalaria glabrata, Schistosoma mansoni cercariae, Artemia salina and Tilapia nilotica.
PubMed:Synthesis and preliminary pharmacological evaluation of new (+/-) 1,4-naphthoquinones structurally related to lapachol.
PubMed:Radermachera xylocarpa: the highly efficient source of lapachol and synthesis of its derivatives.
PubMed:Toxicology of Lapachol in rats: embryolethality.
PubMed:Molluscicidal and trypanocidal activities of lapachol derivatives.
PubMed:Occupational allergic contact dermatitis caused by wood dusts.
PubMed:Chemical reactivity studies with naphthoquinones from Tabebuia with anti-trypanosomal efficacy.
PubMed:In vitro and in vivo Leishmanicidal activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol).
PubMed:Molluscicidal activity of 2-hydroxy-3-alkyl-1,4-naphthoquinones and derivatives.
PubMed:Chemical characterization and biological activity of Macfadyena unguis-cati (Bignoniaceae).
PubMed:Chemical constituents of Avicennia alba. Isolation and structural elucidation of new naphthoquinones and their analogues.
PubMed:Interceptive effect of Lapachol in rats.
PubMed:Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid.
PubMed:Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth.
PubMed:Antimicrobial and antiinflammatory activities of extracts and constituents of Oroxylum indicum (L.) Vent.
PubMed:Inhibition of nitric oxide formation by neuronal nitric oxide synthase by quinones: nitric oxide synthase as a quinone reductase.
PubMed:Hydroxylated naphthoquinones as substrates for Escherichia coli anaerobic reductases.
PubMed:Bioactivation of lapachol responsible for DNA scission by NADPH-cytochrome P450 reductase.
PubMed:The search for novel anticancer agents: a differentiation-based assay and analysis of a folklore product.
PubMed:Bioactive furonaphtoquinones from Tabebuia barbata (Bignoniaceae).
PubMed:Antibacterial and antifungal compounds from Kigelia pinnata.
PubMed:[Tumors caused by methylcholanthrene and lapachol. Follow-up of development with cytology].
PubMed:Activity of extracts of Kigelia pinnata against melanoma and renal carcinoma cell lines.
PubMed:Comparison of antibacterial and antifungal activities of lapachol and beta-lapachone.
PubMed:Radiosensitization by nickel lapachol.
PubMed:Phytochemical and analgesic investigation of Tabebuia chrysotricha.
PubMed:Screening in vitro of natural products against blood forms of Trypanosoma cruzi.
PubMed:Antiinflammatory action of lapachol.
PubMed:Vitamin K1 2,3-epoxide and quinone reduction: mechanism and inhibition.
PubMed:Sulfaquinoxaline inhibition of vitamin K epoxide and quinone reductase.
PubMed:Inhibition of potentially lethal DNA damage repair in human tumor cells by beta-lapachone, an activator of topoisomerase I.
PubMed:In vitro activity of natural and synthetic naphthoquinones against erythrocytic stages of Plasmodium falciparum.
PubMed:Effect of lapachol, a naphthaquinone isolated from Tectona grandis, on experimental peptic ulcer and gastric secretion.
PubMed:Antiviral activity of naphthoquinones. I. Lapachol derivatives against enteroviruses.
PubMed:Antiviral activity of naphthoquinones. I. Lapachol derivatives against enteroviruses.
PubMed:Lapachol inhibition of DT-diaphorase (NAD(P)H:quinone dehydrogenase).
PubMed:Isolation of lapachol from Diphysa robinoides.
PubMed:Modulation of cytotoxicity of menadione sodium bisulfite versus leukemia L1210 by the acid-soluble thiol pool.
PubMed:Partial transition-state inhibitors of glyoxalase I from human erythrocytes, yeast and rat liver.
PubMed:Potentiation of antimetabolite action by uridylate trapping.
PubMed:Uridylate-trapping sugar analogs in combination with inhibitors of uridylate synthesis de novo and 5-fluorouridine.
PubMed:Lapachol inhibition of vitamin K epoxide reductase and vitamin K quinone reductase.
PubMed:Oxidative ring fission of the naphthoquinones lapachol and dichloroallyl lawsone by Penicillium notatum.
PubMed:Naturally occurring quinones as potential bioreductive alkylating agents.
PubMed:Restoration of active transport of solutes and oxidative phosphorylation by naphthoquinones in irradiated membrane vesicles from Mycobacterium phlei.
PubMed:Microbial transformations of natural antitumor agents: conversion of lapachol to dehydro-alpha-lapachone by Curvularia lunata.
PubMed:Dichloroallyl lawsone.
PubMed:In vitro and in vivo evaluation of the toxicity of 1,4-naphthoquinone and 1,2-naphthoquinone derivatives against Trypanosoma cruzi.
PubMed:Microbial transformations of natural antitumor agents: oxidation of lapachol by Penicillium notatum.
PubMed:The sensitizing capacity of naturally occurring quinones. Experimental studies in guinea pigs. I. Naphthoquinones and related compounds.
PubMed:Schistosomiasis mansoni: blockage of cercarial skin penetration by chemical agents: i. naphthoquinones and derivatives.
PubMed:Pharmacology of antitumor agents from higher plants.
PubMed:Lapachol: a new acid-base indicator.
PubMed:A lapachol derivative active against mouse lymphocytic leukemia P-388.
PubMed:Early clinical studies with lapachol (NSC-11905).
PubMed:Quinone natural products: streptonigrin (NSC-45383) and lapachol (NSC-11905) structure-activity relationships.
PubMed:Schistosoma mansoni chemoprophylaxis with dietary lapachol.
PubMed:[Antimicrobial substances from higher plants. XXXV. Antimicrobial or antineoplastic activity of lawsona (2-hydroxy-1,4-naphthoquinone) in comparison with lapachol (2-hydroxy-3-(-3-methyl-2-butanyl)-1,4-naphthoquinone].
PubMed:Function of ubiquinone in electron transport from reduced nicotinamide adenine dinucleotide to nitrate and oxygen in Aerobacter aerogenes.
PubMed:Oral toxicology studies with lapachol.
PubMed:Fluorometric method for the determination of lapachol in serum.
PubMed:The induction of ATP energized mitochondrial volume changes by the combination of the two antitumor age agents showdomycin and lapachol.
PubMed:Lapachol.
PubMed:Syntheses in the lapachol series.
PubMed:Hooker's researches on lapachol in relation to new developments in the field of chemotherapy.
 
Notes:
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