Compounds > avarone
Page last updated: 2024-12-06

avarone

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Description

avarone: antileukemic agent; isolated from Dysidea avara [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72186
CHEMBL ID464645
SCHEMBL ID1014559
MeSH IDM0134391

Synonyms (19)

Synonym
2,5-cyclohexadiene-1,4-dione, 2-((1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-, (1r-(1-alpha,2-beta,4a-beta,8a-alpha))-
nsc 607774
brn 1991429
avarone
2,5-cyclohexadiene-1,4-dione, 2-[[(1r,2s,4as,8as)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]methyl]-
NSC607774 ,
2-[[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-1,4-benzoquinone
CHEMBL464645
avrone
neoavarone
SCHEMBL1014559
VPRHEJGLNUDEEH-LWILDLIXSA-N
DTXSID40203851
awaron
2-[[(1r,2s,4as,8as)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]methyl]-2,5-cyclohexadiene-1,4-dione
2,5-cyclohexadiene-1,4-dione, 2-[(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl]-, [1r-(1alpha,2beta,4abeta,8aalpha)]-
avarone, (+)-
ZR36JQ984T
(+)-avarone

Research Excerpts

Overview

Avarone (AQ) is a naturally occurring sesquiterpenoid benzoquinone possessing antileukaemic activity.

ExcerptReferenceRelevance
"Avarone (AQ) is a naturally occurring sesquiterpenoid benzoquinone possessing antileukaemic activity. "( Arylation of sulfhydryl groups in vitro by the naturally occurring sesquiterpenoid benzoquinone avarone.
Belisario, MA; De Rosa, S; Maturo, M; Pecce, R, 1994)		1.95
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (64)

Assay IDTitleYearJournalArticle
AID1253989Cytotoxicity against human Fem-X cells assessed as cell survival after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1254017Antifungal activity against Aspergillus brasiliensis ATCC 16404 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1310601Induction of apoptosis in human NCI-H460 cells assessed as dead cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 1.2%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310606Induction of apoptosis in human HaCaT cells assessed as live cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 96.8%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1253990Cytotoxicity against human K562 cells assessed as cell survival after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1253991Cytotoxicity against human MDA-MB-453 cells assessed as cell survival after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1254014Antibacterial activity against Pseudomonas aeruginosa ATCC 9027 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID466581Cytotoxicity against human K562 cells by MTT assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1310608Induction of apoptosis in human HaCaT cells assessed as late apoptotic/necrotic cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 0.2%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310604Induction of apoptosis in multidrug resistant human NCI-H460 cells assessed as late apoptotic/necrotic cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 1%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1254006Antibacterial activity against Kocuria rhizophila ATCC 9341 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1666596Induction of DNA damage in human SU8686 cells assessed as increase in gammaH2AX phosphorylation at ser193 at cytotoxic IC50 in presence of 5 uM cisplatin by fluorometry method2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID1310605Induction of apoptosis in multidrug resistant human NCI-H460 cells assessed as dead cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 1.5%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310575Cytotoxicity against human HaCaT cells after 72 hrs by MTT assay2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1666597Induction of DNA damage in human SU8686 cells assessed as increase in gammaH2AX phosphorylation at ser193 at cytotoxic IC50 in presence of 0.3 uM doxorubicin by fluorometry method2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID436264Antimicrobial activity against Escherichia coli DSM 498 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID392420Antiviral activity against HIV12009Bioorganic & medicinal chemistry letters, Jan-15, Volume: 19, Issue:2
A novel sesquiterpene quinone from Hainan sponge Dysidea villosa.
AID436261Antimicrobial activity against Bacillus subtilis subsp. spizizenii DMS 347 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID1253988Cytotoxicity against human A549 cells assessed as cell survival after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID436260Antioxidant activity assessed as DPPH radical scavenging activity2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID1254015Antifungal activity against Candida albicans ATCC 10231 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1310579Selectivity ratio of IC30/IC50 for human NCI-H460 cells to IC30/IC50 for multidrug resistant human NCI-H460 cells2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310574Cytotoxicity against multidrug resistant human NCI-H460 cells after 72 hrs by MTT assay2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID436266Inhibition of acetylcholinesterase2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID466601Antibacterial activity against Escherichia coli ATCC 35218 by serial dilution method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1254012Antibacterial activity against Proteus hauseri ATCC 13315 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID9027Cytotoxic activity against cultured cells of A-549 human lung carcinoma.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID106308Cytotoxic activity against cultured cells of MEL-28 malign human melanoma.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID355617Antitumor activity against Agrobacterium tumefaciens-induced crown gall tumors in potato tubers by potato disk assay
AID466583Cytotoxicity against human phytohemagglutininin-stimulated PBMC cells assessed as growth inhibition by MTT assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID355616Toxicity in brine shrimp
AID1254013Antibacterial activity against Salmonella enterica ATCC 13076 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID436263Antimicrobial activity against Saccharomyces cerevisiae DMS 70449 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID466600Antibacterial activity against Staphylococcus aureus ATCC 25923 by serial dilution method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1310573Cytotoxicity against human NCI-H460 cells after 72 hrs by MTT assay2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310576Selectivity ratio of IC30/IC50 for human HaCaT cells to IC30/IC50 for human NCI-H460 cells2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1254010Antibacterial activity against Clostridium sporogenes ATCC 19404 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID152264Cytotoxic Activity against cultured cells of P-388 murine leukemia.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID1310581Induction of superoxide anion generation in multidrug resistant human NCI-H460 cells at 25 uM after 72 hrs by DHE staining-based flow cytometric analysis relative to control2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1254005Antibacterial activity against Staphylococcus aureus ATCC 6538 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1254007Antibacterial activity against Bacillus subtilis ATCC 6633 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1310603Induction of apoptosis in multidrug resistant human NCI-H460 cells assessed as early apoptotic cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 1.1%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310599Induction of apoptosis in human NCI-H460 cells assessed as early apoptotic cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 0.3%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310598Induction of apoptosis in human NCI-H460 cells assessed as live cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 98.3%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID466582Cytotoxicity against human PBMC cells by MTT assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1254009Antibacterial activity against Micrococcus flavus ATCC 10240 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1254016Antifungal activity against Saccharomyces cerevisiae ATCC 9763 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID436265Toxicity against Artemia salina after 24 hrs2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID466604Toxicity against freshly hatched nauplii of brine shrimp after 24 hrs2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID466579Cytotoxicity against human HeLa cells assessed as decrease in total cellular protein by kenacid blue R binding method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1310602Induction of apoptosis in multidrug resistant human NCI-H460 cells assessed as live cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 96.4%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID466580Cytotoxicity against human Fem-X cells assessed as decrease in total cellular protein by kenacid blue R binding method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1253992Cytotoxicity against human MRC5 cells assessed as cell survival after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1254008Antibacterial activity against Micrococcus luteus ATCC 4698 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1310600Induction of apoptosis in human NCI-H460 cells assessed as late apoptotic/necrotic cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 0.2%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1253987Cytotoxicity against human HeLa cells assessed as cell survival after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID436262Antimicrobial activity against Micrococcus luteus DMS 348 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID1310609Induction of apoptosis in human HaCaT cells assessed as dead cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 2.8%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1254018Cytotoxicity in Brine shrimp assessed as nauplii mortality after 24 hrs2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1310577Selectivity ratio of IC30/IC50 for human HaCaT cells to IC30/IC50 for multidrug resistant human NCI-H460 cells2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID83585Cytotoxic activity against cultured cells of HT-29 human colon carcinoma.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID1254011Antibacterial activity against Escherichia coli ATCC 25922 after 24 hrs by microbroth double dilution method2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
AID1310580Induction of superoxide anion generation in human NCI-H460 cells at 25 uM after 72 hrs by DHE staining-based flow cytometric analysis relative to control2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
AID1310607Induction of apoptosis in human HaCaT cells assessed as early apoptotic cells at 25 uM after 72 hrs by annexin-V/propidium iodide staining-based flow cytometric analysis (Rvb = 0.2%)2016European journal of medicinal chemistry, Aug-08, Volume: 118Simple avarone mimetics as selective agents against multidrug resistant cancer cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (17.86)18.7374
1990's6 (21.43)18.2507
2000's7 (25.00)29.6817
2010's8 (28.57)24.3611
2020's2 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.86

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 Index30.86 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.86)

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%
Other30 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
hydroquinone
[no description available]		2.1310benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
3-methylcholanthrene
Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.		1.9710ortho- and peri-fused polycyclic arenearyl hydrocarbon receptor agonist;
carcinogenic agent
ethidium
Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.		2.0810phenanthridinesfluorochrome;
intercalator
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		1.9810aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
kojic acid
[no description available]		2.25104-pyranones;
enol;
primary alcohol		Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent
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).		7.51201,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		1.9710barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
temozolomide
[no description available]		2.1710imidazotetrazine;
monocarboxylic acid amide;
triazene derivative		alkylating agent;
antineoplastic agent;
prodrug
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		1.9910adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
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.		7.110amino 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
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.0410benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
aloe emodin
aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.		2.2510aromatic primary alcohol;
dihydroxyanthraquinone		antineoplastic agent;
plant metabolite
caproamide
[no description available]		2.2510primary carboxamide;
primary fatty amide
2-tert-butyl-4-quinone
2-tert-butyl-4-quinone: a metabolite of butylated hydroxyanisole ; structure given in first source		2.5220
tetradecanoylphorbol acetate
Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.		1.9810acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
amikacin
Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.		2.5220alpha-D-glucoside;
amino cyclitol glycoside;
aminoglycoside;
carboxamide		antibacterial drug;
antimicrobial agent;
nephrotoxin
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.0410chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
viridicatin
viridicatin: structure. viridicatin : A hydroxyquinolone that is 3-hydroxyuinolin-2(1H)-one which is substituted at position 4 by a phenyl groups. Isolated from the mycelium of several Penicillium species, it exhibits strong antibiotic activity against M. tuberculosis and also against B. subtilis, S. aureus and S. cerevisiae.		2.2510hydroxyquinolineantibacterial agent;
Aspergillus metabolite;
marine metabolite;
Penicillium metabolite
pinocembrin
pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.		2.2510(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent
avarol
avarol: RN given refers to parent cpd; extract from Dysidea avara(sea sponge)		4.4210
illimaquinone
illimaquinone: structure given in first source; isolated from the Red Sea sponge Smenospongia; inhibits the RNase H. activity of HIV-1 reverse transcriptase		2.0110monohydroxy-1,4-benzoquinones;
prenylquinone		metabolite
skyrin
skyrin: main pigment of toxin rice fungus Penicillium islandicum; RN given refers to parent cpd; structure		2.2510biaryl;
trihydroxyanthraquinone
altersolanol a
altersolanol A: isolated from fermentation product of fungus Alternaria porri(Ellis) Ciferri;RN given refers to (1R-(1alpha,2beta,3beta,4alpha))-isomer; structure given in first source		2.2510pentahydroxyanthraquinone
xanthorrhizol
xanthorrhizol: structure in first source		2.2510sesquiterpenoid
aeroplysinin i
aeroplysinin I: isolated from sponge Aplysina sp.; RN refers to (1S-trans)-isomer; structure given in second source		2.2510tertiary alcohol
matairesinol
matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).		2.2510gamma-lactone;
lignan;
polyphenol		angiogenesis inhibitor;
anti-asthmatic agent;
phytoestrogen;
plant metabolite
macrosporin
macrosporin: isolated from fermentation product of fungus Alternaria porri (Ellis) Ciferri; structure given in first source		2.2510
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.3920icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
farnesol
Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.		2.0210farnesolplant metabolite
sesquiterpenes
[no description available]		4.53240
nadp
[no description available]		1.9810
beauvericin
[no description available]		2.2510cyclodepsipeptideantibiotic insecticide;
antifungal agent;
antineoplastic agent;
apoptosis inhibitor;
fungal metabolite;
ionophore;
mycotoxin;
P450 inhibitor
8-hydroxymanzamine a
8-hydroxymanzamine A: active against HIV-II; isolated from the sponge Pachypellina; structure in first source. 8-hydroxymanzamine A : An alkaloid that is manzamine A with a hydroxy substituent at position 8. Isolated from Pachypellina and Acanthostrongylophora, it exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).		2.2510alkaloid;
beta-carbolines;
isoquinolines		anti-HSV-2 agent;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
metabolite
thromboxane b2
Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.		1.9910thromboxanes Bhuman metabolite;
mouse metabolite
neobavaisoflavone
neobavaisoflavone: isolated from Psoralea corylifolia; structure in first source. neobavaisoflavone : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone with an additonal hydroxy group at position 4' and a prenyl group at position 3'. Isolated from seeds of Psoralea corylifolia, it exhibits inhibitory activity against DNA polymerase and platelet aggregation.		2.25107-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
plant metabolite;
platelet aggregation inhibitor
alternariol monomethyl ether
djalonensone : A benzochromenone that is alternariol in which the hydroxy group at position 9 has been converted into the corresponding methyl ether. A natural product found in Chaetomium globosum as well as being one of the two most important compounds belonging to the group of Altenaria mycotoxins.		2.2510aromatic ether;
benzochromenone		antifungal agent;
fungal metabolite;
mycotoxin
luffariellolide
luffariellolide: structure given in first source; a partially reversible phospholipase A2 inhibitor; a major metabolite of the sponge Luffariella; do not confuse with luffolide, a minor metabolite of the same species		2.2510diterpene lactone
bakuchiol
bakuchiol: chief component of Psoralea corylifolia Linn; structure		2.2510
aureol
aureol: from the Jamaican sponge Smenospongia aurea; structure in first source		7.0410coumestans
bavachalcone
bavachalcone: structure in first source		2.2510chalcones
gentamicin sulfate
[no description available]		2.0410
bolinaquinone
bolinaquinone: a marine sesquiterpenoid from sponge Dysidea sp. with anti-inflammatory activity; structure in first source		2.0510
aerothionin
[no description available]		2.2510isoxazolesmetabolite
nystatin a1
Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.		2.7830nystatins
roquefortine
[no description available]		2.2510pyrroloindole
muramidase
Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.		2.0710
deoxyguanosine triphosphate
[no description available]		1.9710deoxyguanosine phosphate;
guanyl deoxyribonucleotide;
purine 2'-deoxyribonucleoside 5'-triphosphate		Arabidopsis thaliana metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
dacarbazine
(E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.		2.1710dacarbazine
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Cervix
[description not available]		02.0510
Uterine Cervical Neoplasms
Tumors or cancer of the UTERINE CERVIX.		02.0510
Benign Neoplasms, Brain
[description not available]		02.1710
Glial Cell Tumors
[description not available]		02.1710
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.1710
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		07.1710
Cancer of Lung
[description not available]		02.110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.110
Anasarca
[description not available]		01.9810
Innate Inflammatory Response
[description not available]		01.9810
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		01.9810
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		01.9810
Cancer of Liver
[description not available]		01.9810
Liver Neoplasms
Tumors or cancer of the LIVER.		01.9810
Hepatoblastoma
A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)		01.9810
Acquired Immune Deficiency Syndrome
[description not available]		06.9710
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		01.9710
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		01.9710
Leucocythaemia
[description not available]		01.9610
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)		01.9610