Compounds > beauvericin
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beauvericin

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Description

Beauvericin is a cyclic hexadepsipeptide mycotoxin produced by various fungi, particularly Fusarium and Beauveria species. It exhibits a wide range of biological activities, including immunosuppressive, cytotoxic, and antibiotic effects. Its synthesis involves the condensation of three amino acids (D-hydroxyisovaleric acid, L-N-methyl-L-valine, and L-phenylalanine) and three non-proteinogenic amino acids (L-N-methyl-L-isoleucine, L-N-methyl-L-phenylalanine, and L-N-methyl-L-leucine). Beauvericin's toxicity stems from its ability to disrupt cellular ion transport, particularly potassium, leading to mitochondrial dysfunction and apoptosis. It is studied extensively due to its potential implications in food safety, animal health, and human health. Its presence in contaminated food products poses a risk to consumers, and it can cause various health problems in animals. Research on beauvericin focuses on understanding its biosynthesis, toxicity mechanisms, and developing strategies for its detection and mitigation. It is also investigated for its potential as a biocontrol agent against insects and fungi.'

beauvericin: 18-membered cyclodepsipeptides [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

beauvericin : A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues. [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]

Cross-References

ID SourceID
PubMed CID3007984
CHEMBL ID249052
CHEBI ID3000
SCHEMBL ID29355
MeSH IDM0045517
PubMed CID105014
CHEMBL ID1977672
SCHEMBL ID6452789
MeSH IDM0045517

Synonyms (30)

Synonym
(3s,6r,9s,12r,15s,18r)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
CHEBI:3000 ,
(3s,6r,9s,12r,15s,18r)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
unii-26s048ls2r
26s048ls2r ,
SCHEMBL29355
CHEMBL249052
(3s,6r,9s,12r,15s,18r)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexaone
NCGC00380798-01
AKOS030622850
DTXSID00891834
CS-W020817
HY-N6739
cyclo(d-.alpha.-hydroxyisovaleryl-n-methyl-l-phenylalanyl-d~ -.alpha.-hydroxyisovaleryl-n-methyl-l-phenylalanyl-d-.alpha.-hydroxyisovaleryl-n-methyl-l-phenylalanyl)
NCI60_038416
beauvericin
26048-05-5
beauvericin, >=97% (hplc)
nsc-708472
1,13-trioxa-4,10,16-triazacyclooctadecane, cyclic peptide deriv.
nsc708472
3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
FT-0602893
SCHEMBL6452789
CHEMBL1977672
beauvericin, vetranal(tm), analytical standard
J-016236
cyclo(d-??-hydroxyisovaleryl-l-n-methyl-phe)3
(3s,6r,9s,12r,15s,18r)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tripropan-2-yl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
n-methylcyclo(l-phe-d-hmb-n-methyl-l-phe-d-hmb-n-methyl-l-phe-d-hmb-)

Research Excerpts

Overview

Beauvericin (BEA) is a depsipeptide with antimicrobial, anti-inflammatory, and anti-cancer activities isolated from Beaveria bassiana. It is a world-spread mycotoxin isolated from the traditional Chinese medicine, Bombyx batryticatus.

ExcerptReferenceRelevance
"Beauvericin (BEA) is a secondary metabolite produced by the fungus Beauveria bassiana."( In silico evidence of beauvericin antiviral activity against SARS-CoV-2.
Al Khoury, C; Bashir, Z; Merhi, G; Nemer, G; Nemer, N; Tokajian, S, 2022)		1.76
"Beauvericin (BEA) is a well-known mycotoxin produced by many fungi, including Beaveria bassiana. "( Study on In Vitro Metabolism and In Vivo Pharmacokinetics of Beauvericin.
Li, Y; Meng, G; Wu, C; Yuan, Y, 2022)		2.41
"Beauvericin (BEA) is a depsipeptide with antimicrobial, anti-inflammatory, and anti-cancer activities isolated from Beauveria bassiana. "( In vitro anti-cancer effects of beauvericin through inhibition of actin polymerization and Src phosphorylation.
Cho, JY; Kim, HG; Kim, JH; Sung, NY, 2023)		2.64
"Beauvericin is a world-spread mycotoxin isolated from the traditional Chinese medicine, Bombyx batryticatus (BB), which has been widely used to treat various neoplastic diseases. "( Beauvericin exerts an anti-tumor effect on hepatocellular carcinoma by inducing PI3K/AKT-mediated apoptosis.
Jin, M; Li, J; Li, M; Liu, W; Qiao, Y; Song, Y; Wang, G; Yang, D; Yin, J; Zhao, Y, 2023)		3.8
"Beauvericin (BEA) is an emerging mycotoxin produced by some species of Fusarium genera that widely contaminates food and feed. "( Beauvericin Immunotoxicity Prevention by
Cimbalo, A; Di Matteo, G; Mannina, L; Manyes, L, 2023)		3.8
"Beauvericin (BEA) is a mycotoxin produced by Beauveria bassiana and Fusarium species recently reported as toxic on porcine oocyte maturation and embryo development. "( The mycotoxin beauvericin induces oocyte mitochondrial dysfunction and affects embryo development in the juvenile sheep.
Ciani, E; Dell'Aquila, ME; Lacalandra, GM; Martino, NA; Marzano, G; Mastrorocco, A; Minervini, F; Roelen, BAJ, 2019)		2.32
"Beauvericin (BEA) is a natural bioactive compound, with a dual nature. "( Beauvericin: The beauty and the beast.
Anadón, A; Bertero, A; Caloni, F; Fossati, P, 2020)		3.44
"Beauvericin (BEA) is a non-legislated emergent mycotoxin while Ochratoxin A (OTA) has been widely studied and legislated."( Beauvericin and ochratoxin A mycotoxins individually and combined in HepG2 cells alter lipid peroxidation, levels of reactive oxygen species and glutathione.
Ben-Mahmoud, M; Carbone, S; Juan-García, A; Mañes, J; Sagratini, G, 2020)		2.72
"Beauvericin (BEA) is a member of the enniatin family of mycotoxins which has received increasing interest because of frequent occurrence in food and feed. "( Beauvericin alters the expression of genes coding for key proteins of the mitochondrial chain in ovine cumulus-oocyte complexes.
Ciani, E; Dell'Aquila, ME; Mastrorocco, A; Minervini, F; Nicassio, L; Roelen, BAJ, 2021)		3.51
"Beauvericin is an ubiquitous mycotoxin with relevant occurrence in food and feed. "( The mycotoxin beauvericin impairs development, fertility and life span in the nematode Caenorhabditis elegans accompanied by increased germ cell apoptosis and lipofuscin accumulation.
Baier, S; Büchter, C; Freyer, M; Honnen, S; Koch, K; Saier, C; Wätjen, W, 2020)		2.36
"Beauvericin (BEA) is a mycotoxin present in cereals that produces cytotoxicity, intracellular reactive oxygen species and lipid peroxidation."( Antioxidant capacity of trans-resveratrol dietary supplements alone or combined with the mycotoxin beauvericin.
Brandolini, V; Font, G; Maietti, A; Mallebrera, B; Ruiz, MJ; Tedeschi, P, 2017)		1.39
"Beauvericin (BEA) is a mycotoxin produced by many species of fungus Fusarium and by Beauveria bassiana; BEA is a natural contaminant of cereals and cereals based products and possesses a wide variety of biological properties. "( In vitro mechanisms of Beauvericin toxicity: A review.
Font, G; Mallebrera, B; Prosperini, A; Ruiz, MJ, 2018)		2.23
"Beauvericin is a mycotoxin which has insecticidal, anti-microbial, anti-viral and anti-cancer activities. "( Beauvericin synthetase contains a calmodulin binding motif in the entomopathogenic fungus Beauveria bassiana.
Kim, J; Sung, GH, 2018)		3.37
"Beauvericin (BEA) is a cyclic hexadepsipeptide, which derives from Cordyceps cicadae. "( Beauvericin, A Fusarium Mycotoxin: Anticancer Activity, Mechanisms, and Human Exposure Risk Assessment.
Kuca, K; Patocka, J; Wu, Q, 2019)		3.4
"Beauvericin (BEA) is a bioactive compound produced by the secondary metabolism of several Fusarium strains with a strong antibacterial, antifungal, and insecticidal activities. "( A chemical approach for the reduction of beauvericin in a solution model and in food systems.
Luciano, FB; Mañes, J; Manyes, L; Meca, G, 2014)		2.11
"Beauvericin is a world-spread mycotoxin with a high toxicity in mammalian cells. "( The mycotoxin beauvericin induces apoptotic cell death in H4IIE hepatoma cells accompanied by an inhibition of NF-κB-activity and modulation of MAP-kinases.
Chovolou, Y; Debbab, A; Hohlfeld, A; Proksch, P; Wätjen, W, 2014)		2.21
"Beauvericin (BEA) is a secondary metabolite produced by many species of fungus Fusarium. "( Mechanisms of beauvericin toxicity and antioxidant cellular defense.
Font, G; Juan-Garcia, A; Mallebrera, B; Ruiz, MJ, 2016)		2.24
"Beauvericin (BEA) is a cyclic hexadepsipeptide that derives from Codyceps cicadae. "( Beauvericin-induced cell apoptosis through the mitogen-activated protein kinase pathway in human nonsmall cell lung cancer A549 cells.
Chen, BF; Jow, GM; Lin, HI; Lu, CL, 2016)		3.32
"Beauvericin is a secondary metabolite natural product from microorganisms and has been shown to have a new potential antifungal activity. "( An inhibition study of beauvericin on human and rat cytochrome P450 enzymes and its pharmacokinetics in rats.
Dai, R; Mei, L; Zhang, L, 2009)		2.11
"Beauvericin is a naturally occurring cyclohexadepsipeptide originally described from Beauveria bassiana but also reported from several Fusarium species as well as members of the genus Isaria. "( A beauvericin hot spot in the genus Isaria.
Berkaew, P; Hywel-Jones, NL; Isaka, M; Luangsa-Ard, JJ; Ridkaew, R, 2009)		2.52
"Beauvericin (BEA) is a cyclic hexadepsipeptide mycotoxin with notable phytotoxic and insecticidal activities. "( Modeling of Fusarium redolens Dzf2 mycelial growth kinetics and optimal fed-batch fermentation for beauvericin production.
Liu, YS; Wu, JY; Xu, LJ; Zhou, LG, 2011)		2.03
"Beauvericin is a mycotoxin with antiviral, antibacterial, nematicidal, insecticidal, cytotoxic, and apoptotic activity. "( Beauvericin induced erythrocyte cell membrane scrambling.
Kucherenko, Y; Lang, F; Qadri, SM, 2011)		3.25
"Beauvericin is a cyclic hexadepsipeptide mycotoxin, which has insecticidal, antimicrobial, antiviral and cytotoxic activities. "( Beauvericin, a bioactive compound produced by fungi: a short review.
Wang, Q; Xu, L, 2012)		3.26
"Beauvericin (BEA) is a bioactive compound produced by the secondary metabolism of several Fusarium strains and is known to have various biological activities. "( Influence of different soluble dietary fibers on the bioaccessibility of the minor Fusarium mycotoxin beauvericin.
Font, G; Mañes, J; Meca, G; Meneghelli, G; Ritieni, A, 2012)		2.04
"Beauvericin (BEA) is a bioactive compound produced by the secondary metabolism of several Fusarium strains and known to have various biological activities. "( Chemical reduction of the mycotoxin beauvericin using allyl isothiocyanate.
Luciano, FB; Mañes, J; Meca, G; Tsao, R; Zhou, T, 2012)		2.1
"Beauvericin (BEA) is a cyclohexadepsipeptide mycotoxin which has insecticidal properties and produces cytotoxic effects in mammalian cells. "( Study of the cytotoxic activity of beauvericin and fusaproliferin and bioavailability in vitro on Caco-2 cells.
Font, G; Meca, G; Prosperini, A; Ruiz, MJ, 2012)		2.1
"Beauvericin is a mycotoxin that infects a wide variety of cereal grains. "( Beauvericin activates Ca2+-activated Cl- currents and induces cell deaths in Xenopus oocytes via influx of extracellular Ca2+.
Chen, YW; Chou, CJ; Jeng, CJ; Jow, GM; Tang, CY, 2005)		3.21
"Beauvericin (BEA) is a cyclic hexadepsipeptide produced by Beauveria bassiana, Paecilomyces fumosoroseus, Paecilomyces tenuipes, Polyporus sulphurous, and a variety of Fusarium species. "( [Beauvericin: chemical and biological aspects and occurrence].
Klarić, MS; Pepeljnjak, S, 2005)		2.68
"Beauvericin is a cyclohexadepsipeptide mycotoxin which has insecticidal properties and which can induce apoptosis in mammalian cells. "( Beauvericin production by Fusarium species.
Castella, G; Chelkowski, J; Golinski, P; Kostecki, M; Logrieco, A; Moretti, A; Ritieni, A, 1998)		3.19

Effects

ExcerptReferenceRelevance
"New beauvericins have been synthesized using the nonribosomal peptide synthetase BbBEAS from the entomopathogenic fungus Beauveria bassiana. "( In vitro chemoenzymatic and in vivo biocatalytic syntheses of new beauvericin analogues.
Denisiuk, A; Espinosa-Artiles, P; Feifel, SC; Matthes, D; Molnár, I; Müller, J; Richter, L; Süssmuth, RD; Xu, Y, 2012)		1.17

Actions

ExcerptReferenceRelevance
"Beauvericin at a lower concentration (10(-6) M) competitively inhibited the Ca2+-induced contraction in depolarized muscle, whereas higher concentrations (3 x 10(-6) or 10(-5) M) non-competitively inhibited this contraction."( Inhibitory effect of beauvericin on a high K+-induced tonic contraction in guinea-pig taenia coli.
Kimura, M; Kitayama, T; Matsuoka, K; Nakajyo, S; Shimizu, K; Urakawa, N; Yamamura, Y, 1987)		1.31

Toxicity

Beauvericin (BEA) and enniatins are toxic ionophoric cyclodepsipeptides that mainly occur in grains.

ExcerptReferenceRelevance
"The cyclic hexadepsipeptide beauvericin, initially known as a secondary metabolite produced by the entomopathogenic fungus Beauveria bassiana and toxic to Artemia salina larvae, has been more recently recognized as an important mycotoxin synthesized by a number of Fusarium strains, which parasite maize, wheat and rice."( Beauvericin cytotoxicity to the invertebrate cell line SF-9.
Caiaffa, MF; Calo', L; Fornelli, F; Macchia, L; Nenna, S; Tursi, A, 2003)		2.06
" This study indicates that enniatins, fungal metabolites that are commonly found in grain in Northern Europe, may have an underestimated toxic potential."( Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum.
Eriksen, GS; Ivanova, L; Skjerve, E; Uhlig, S, 2006)		0.33
" However, data from the brine shrimp bioassay showed that further toxic metabolites within this complex need to be characterized."( Further data on the production of beauvericin, enniatins and fusaproliferin and toxicity to Artemia salina by Fusarium species of Gibberella fujikuroi species complex.
Logrieco, A; Moretti, A; Mulè, G; Ritieni, A, 2007)		0.62
"5) estimated by MTT reduction assay shows that BEA is three times more toxic than OTA."( Beauvericin and ochratoxin A genotoxicity evaluated using the alkaline comet assay: single and combined genotoxic action.
Darabos, D; Kasuba, V; Klarić, MS; Pepeljnjak, S; Rozgaj, R, 2010)		1.8
" Once the potential interaction has been detected, a quantitative assessment is necessary to ensure and characterize these interactions, that is, each mycotoxin contributes to the toxic effect in accord with its own potency."( Cytotoxic effects of mycotoxin combinations in mammalian kidney cells.
Font, G; Juan-García, A; Macáková, P; Ruiz, MJ, 2011)		0.37
" Our results indicate that the co-occurrence of low concentrations of mycotoxin in food may increase their toxic effects."( Cytotoxic effects induced by patulin, sterigmatocystin and beauvericin on CHO-K1 cells.
Abid-Essefi, S; Bacha, H; Berrada, H; Mallebrera, B; Ruiz, MJ; Zouaoui, N, 2016)		0.68
" Unfortunately, we still know very little about the bioavailability and toxic potentials of many of these less characterized mycotoxins, including the large family of enniatins."( Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform.
Have Rasmussen, P; Jensen, U; Lund Hansen, N; Svingen, T; Taxvig, C; Vinggaard, AM, 2017)		0.81
"Emerging Fusarium mycotoxins include the toxic secondary metabolites fusaproliferin, enniatins, beauvericin (BEA), and moniliform."( Occurrence, toxicity, bioaccessibility and mitigation strategies of beauvericin, a minor Fusarium mycotoxin.
Luciano, FB; Luz, C; Mañes, J; Meca, G; Saladino, F, 2017)		0.91
" OTA was the least toxic mycotoxin and DON and BEA showed similar acute toxicity."( Cytotoxicity against fish and mammalian cell lines and endocrine activity of the mycotoxins beauvericin, deoxynivalenol and ochratoxin-A.
Fernández-Cruz, ML; García-Herranz, V; Navas, JM; Valdehita, A, 2019)		0.73
"Beauvericin (BEA) and enniatins are toxic ionophoric cyclodepsipeptides that mainly occur in grains."( Counteracting in Vitro Toxicity of the Ionophoric Mycotoxin Beauvericin-Synthetic Receptors to the Rescue.
De Saeger, S; Decleer, M; Madder, A; Ornelis, V; Rajkovic, A; Sas, B, 2019)		2.2
" Cyclodepsipeptides are fungal molecules with potentially adverse and positive effects."( Comparative Structure-Activity Analysis of the Antimicrobial Activity, Cytotoxicity, and Mechanism of Action of the Fungal Cyclohexadepsipeptides Enniatins and Beauvericin.
Baydoun, E; Courvoisier-Dezord, E; Hijazi, A; Lafond, M; Maresca, M; Nicoletti, C; Olleik, H; Perrier, J; Xue, P, 2019)		0.71

Pharmacokinetics

ExcerptReferenceRelevance
"o administration alone and co-administration with ketoconazole, which indicated a pharmacodynamic function may play a role in the synergistic effect on antifungal activity."( An inhibition study of beauvericin on human and rat cytochrome P450 enzymes and its pharmacokinetics in rats.
Dai, R; Mei, L; Zhang, L, 2009)		0.66
" The purpose of this study was to evaluate the in vitro distribution and metabolism characteristics as well as the in vivo pharmacokinetic (PK) profile of BEA."( Study on In Vitro Metabolism and In Vivo Pharmacokinetics of Beauvericin.
Li, Y; Meng, G; Wu, C; Yuan, Y, 2022)		0.96

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51
" However, both mycotoxins potently interact with ABCB1 and ABCG2 transport functions suggesting influences on bioavailability of xenobiotics and pharmaceuticals."( Interactions between ABC-transport proteins and the secondary Fusarium metabolites enniatin and beauvericin.
Berger, W; Chiba, P; Dornetshuber, R; Heffeter, P; Koellensperger, G; Kopp, S; Lemmens-Gruber, R; Micksche, M; Schumacher, R; Sulyok, M, 2009)		0.57
" The aim of this study was to determine the cytotoxicity of BEA and FUS in human epithelial colorectal adenocarcinoma HT-29 and Caco-2 cells, the transepithelial transport and the bioavailability using Caco-2 cells as a simulated in vitro gastrointestinal model of the human intestinal epithelium."( Study of the cytotoxic activity of beauvericin and fusaproliferin and bioavailability in vitro on Caco-2 cells.
Font, G; Meca, G; Prosperini, A; Ruiz, MJ, 2012)		0.66
" Unfortunately, we still know very little about the bioavailability and toxic potentials of many of these less characterized mycotoxins, including the large family of enniatins."( Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform.
Have Rasmussen, P; Jensen, U; Lund Hansen, N; Svingen, T; Taxvig, C; Vinggaard, AM, 2017)		0.81
" Finally, the absolute bioavailability of BEA was evaluated by intravenous and oral administration in rats."( Study on In Vitro Metabolism and In Vivo Pharmacokinetics of Beauvericin.
Li, Y; Meng, G; Wu, C; Yuan, Y, 2022)		0.96

Dosage Studied

ExcerptRelevanceReference
" Specifically, a microbial natural product library was screened for hits that synergize the effect of a low dosage of ketoconazole (KTC) that alone shows little detectable fungicidal activity."( High-throughput synergy screening identifies microbial metabolites as combination agents for the treatment of fungal infections.
An, R; Bian, J; Chen, X; Chen, Z; Dai, H; Fu, C; Gao, H; Goodfellow, M; Huang, R; Jiang, Y; Kuai, J; Liu, J; Liu, Z; Min, F; Pei, G; Song, Y; Sun, H; Sun, N; Wang, J; Yan, K; Yang, K; You, J; Yu, Z; Zhang, L; Zhang, S; Zhang, X; Zhang, Y; Zhao, W; Zheng, C; Zhou, G; Zhuo, Y, 2007)		0.34
" For example, the accuracy and the precision of the method were determined by a recovery study at 80, 100 and 120% of the tablet dosage levels."( Development and Validation of Stability-Indicating Method for the Simultaneous Determination of Ketoconazole and Beauvericin in Pharmaceutical Tablets.
Liu, Y; Luan, Y; Tang, X; Tian, T; Yang, M; Zhao, Z; Zhu, M, 2016)		0.65
" BEA showed a weak antagonistic effect at the androgen receptor and OTA produced a biphasic dose-response curve at the estrogen receptor."( Cytotoxicity against fish and mammalian cell lines and endocrine activity of the mycotoxins beauvericin, deoxynivalenol and ochratoxin-A.
Fernández-Cruz, ML; García-Herranz, V; Navas, JM; Valdehita, A, 2019)		0.73
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (8)

RoleDescription
mycotoxinPoisonous substance produced by fungi.
antibiotic insecticidenull
apoptosis inhibitorAny substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ionophoreA compound which can carry specific ions through membranes of cells or organelles.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
P450 inhibitorAn enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role 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]

Drug Classes (1)

ClassDescription
cyclodepsipeptideA depsipeptide in which the amino and hydroxy carboxylic acid residues are connected in a ring.
[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]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1875557Antiproliferative activity against human Huh-7 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay2022Journal of natural products, 11-25, Volume: 85, Issue:11
Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus
AID1666601Induction of DNA damage in human SU8686 cells assessed as increase gammaH2AX protein level at IC50 for 24 hrs in presence of 5 uM cisplatin by western blot analysis2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID1270927Potentiation of antifungal activity of fluconazole against Candida albicans ATCC 24433 by checkerboard assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1875559Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay2022Journal of natural products, 11-25, Volume: 85, Issue:11
Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus
AID1666600Induction of DNA damage in human SU8686 cells assessed as tail DNA formation at IC50 by alkaline Comet assay2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID1270909Antifungal activity against Candida albicans ATCC 24433 assessed as growth inhibition after 24 hrs by broth microdilution assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1270917Antibiofilm activity against Candida albicans ATCC 24433 after 24 hrs in presence of fluconazole by XTT-based colorimetric assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1270919Synergistic antibiofilm activity against Candida albicans ATCC 24433 assessed as fractional inhibition concentration index after 24 hrs in presence of fluconazole checkerboard assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1875558Antiproliferative activity against rat MRMT-1 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay2022Journal of natural products, 11-25, Volume: 85, Issue:11
Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus
AID1270916Antibiofilm activity against Candida albicans ATCC 24433 after 24 hrs by XTT-based colorimetric assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1666603Induction of DNA damage in human SU8686 cells assessed as increase in gammaH2AX nuclear foci under basal condition at IC50 by fluorometry method2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID1270918Synergistic antibiofilm activity against Candida albicans ATCC 24433 assessed as fractional inhibition concentration ratio after 24 hrs in presence of fluconazole by checkerboard assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1270913Antifungal activity against Candida albicans ATCC 24433 assessed as synergistic growth inhibition after 24 hrs in presence of fluconazole by broth microdilution assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1270914Antifungal activity against Candida albicans ATCC 24433 assessed as fractional inhibition concentration ratio in presence of fluconazole by checkerboard assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1270915Antifungal activity against Candida albicans ATCC 24433 assessed as fractional inhibition concentration index in presence of fluconazole by checkerboard assay2015Journal of natural products, Nov-25, Volume: 78, Issue:11
Synergistic Antifungal Meroterpenes and Dioxolanone Derivatives from the Endophytic Fungus Guignardia sp.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (266)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (3.01)18.7374
1990's23 (8.65)18.2507
2000's61 (22.93)29.6817
2010's123 (46.24)24.3611
2020's51 (19.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.99

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

MetricThis Compound (vs All)
Research Demand Index40.99 (24.57)
Research Supply Index5.59 (2.92)
Research Growth Index5.18 (4.65)
Search Engine Demand Index62.80 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (40.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews12 (4.51%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
Other254 (95.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.1110conazole antifungal drug;
difluorobenzene;
tertiary alcohol;
triazole antifungal drug		environmental contaminant;
P450 inhibitor;
xenobiotic
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.4110nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
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
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
amoxicillin
Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.		2.1110penicillin allergen;
penicillin		antibacterial drug
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)		2.2510
avarone
avarone: antileukemic agent; isolated from Dysidea avara		2.2510
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
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
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
bavachalcone
bavachalcone: structure in first source		2.2510chalcones
aerothionin
[no description available]		2.2510isoxazolesmetabolite
roquefortine
[no description available]		2.2510pyrroloindole
alpha-ketoisovalerate
alpha-ketoisovalerate: RN given refers to parent cpd. 3-methyl-2-oxobutanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 3-methyl-2-oxobutanoic acid, arising from deprotonation of the carboxy group.. 3-methyl-2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.		2.13102-oxo monocarboxylic acid;
branched-chain keto acid		human metabolite;
Saccharomyces cerevisiae metabolite
gamma-aminobutyric acid
gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.		2.0110amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
4-hydroxyphenylacetic acid
4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.		2.3110monocarboxylic acid;
phenols		fungal metabolite;
human metabolite;
mouse metabolite;
plant metabolite
acetaldehyde
Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.		210aldehydecarcinogenic agent;
EC 3.5.1.4 (amidase) inhibitor;
electron acceptor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
mutagen;
oxidising agent;
Saccharomyces cerevisiae metabolite;
teratogenic agent
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		2.0210halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
hydrochloric acid
Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.		2.1110chlorine molecular entity;
gas molecular entity;
hydrogen halide;
mononuclear parent hydride		mouse metabolite
nickel
Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.		2.0210metal allergen;
nickel group element atom		epitope;
micronutrient
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		2.0410monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
nitrites
Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)		210monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species		human metabolite
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		1.9710aromatic ether;
nitrile;
polyether;
tertiary amino compound
carbonyl cyanide p-trifluoromethoxyphenylhydrazone
Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.		2.0210aromatic ether;
hydrazone;
nitrile;
organofluorine compound		ATP synthase inhibitor;
geroprotector;
ionophore
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.		2.1710conazole antifungal drug;
difluorobenzene;
tertiary alcohol;
triazole antifungal drug		environmental contaminant;
P450 inhibitor;
xenobiotic
fusaric acid
Fusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.		8.0140aromatic carboxylic acid;
pyridines
gabapentin
Gabapentin: A cyclohexane-gamma-aminobutyric acid derivative that is used for the treatment of PARTIAL SEIZURES; NEURALGIA; and RESTLESS LEGS SYNDROME.. gabapentin : A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.		2.0110gamma-amino acidanticonvulsant;
calcium channel blocker;
environmental contaminant;
xenobiotic
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		7.7530dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
patulin
Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.		2.4820furopyran;
gamma-lactone;
lactol		antimicrobial agent;
Aspergillus metabolite;
carcinogenic agent;
mutagen;
mycotoxin;
Penicillium metabolite
phenindione
Phenindione: An indandione that has been used as an anticoagulant. Phenindione has actions similar to WARFARIN, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)		2.0510aromatic ketone;
beta-diketone		anticoagulant
allyl isothiocyanate
allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.		7.0710alkenyl isothiocyanate;
isothiocyanate		antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
lachrymator;
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.		2.0510amino 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
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		6.9710aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9610amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		1.9910antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
egtazic acid
Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.		2.0210diether;
tertiary amino compound;
tetracarboxylic acid		chelator
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		2.420L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
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.		2.0810aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
taurocholic acid
Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.		210amino sulfonic acid;
bile acid taurine conjugate		human metabolite
nitrobenzene
nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.		2.0810nitroarene;
nitrobenzenes
oleanolic acid
[no description available]		2.4110hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.0510dialdehydebiomarker
trinitrobenzenesulfonic acid
Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.		2.0810arenesulfonic acid;
C-nitro compound		epitope;
explosive;
reagent
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.110acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
tricarballylic acid
tricarballylic acid: RN given refers to parent cpd. tricarballylic acid : A tricarboxylic acid that is glutaric acid in which one of the beta-hydrogens is substituted by a carboxy group.		2.0110tricarboxylic acid
sodium nitrate
sodium nitrate : The inorganic nitrate salt of sodium.		2.0410inorganic nitrate salt;
inorganic sodium salt		fertilizer;
NMR chemical shift reference compound
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.0110benzenes;
phenyl acetates
ursodeoxycholic acid
Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.		210bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human metabolite;
mouse metabolite
nigericin
Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.		1.9710polycyclic etherantibacterial agent;
antimicrobial agent;
bacterial metabolite;
potassium ionophore
etoposide
[no description available]		210beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
deoxynivalenol
deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.		4.12140cyclic ketone;
enone;
primary alcohol;
secondary alpha-hydroxy ketone;
trichothecene;
triol		mycotoxin
moniliformin
moniliformin: RN given refers to parent cpd; structure; do not confuse with plant product, moniliformin		6.36290
fura-2
Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.		2.0110
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.1710D-glucopyranoseepitope;
mouse metabolite
aurofusarin
aurofusarin: from Fusarium graminearum; structure given in first source		2.1310organic heterotricyclic compound;
organooxygen compound
2-hydroxyisovaleric acid
2-hydroxyisovaleric acid: RN given refers to parent cpd without isomeric designation. 2-hydroxy-3-methylbutyric acid : A valine derivative that is valine in which the amino group has been replaced by a hydroxy group.		2.05102-hydroxy monocarboxylic acidhuman metabolite
valerates
Valerates: Derivatives of valeric acid, including its salts and esters.		2.4520short-chain fatty acid anion;
straight-chain saturated fatty acid anion		plant metabolite
culmorin
culmorin: tricyclic sesquiterpene metabolite of fungus Fusarium culmorium; structure. culmorin : A sesquiterpenoid fungal metabolite isolated from Fusarium culmorum.		2.2510
enniatin b
enniatins: cyclohexadepsipeptides containing valine, isoleucine & valeric acid from Fusarian; form complexes with cations & cellular membranes; there are at least three different enniatins H, B & C; minor descriptor (76-86); on-line & INDEX MEDICUS search PEPTIDES, CYCLIC (76-86); see also record for enniatin D, E, F. enniatin B : An enniatin obtained from formal cyclocondensation of three N-[(2R)-2-hydroxy-3-methylbutanoyl]-N-methyl-L-valine units.		7.99800enniatinantimicrobial agent
aflatoxin b1
Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.		2.1110aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human metabolite
lateritin
lateritin: isolated from the mycelial cake of Gibberella lateritium; structure in first source; bassiatin is the (3S,6R) isomer		2.7530
Bardoxolone
[no description available]		2.4110cyclohexenones
nivalenol
nivalenol: RN given refers to 3alpha,4beta,7alpha-isomer		3.0340trichothecene
monensin
Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.		1.9710cyclic hemiketal;
monocarboxylic acid;
polyether antibiotic;
spiroketal		antifungal agent;
coccidiostat;
ionophore
ryanodine
Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.		2.0210
ochratoxin a
ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.		3.5880isochromanes;
monocarboxylic acid amide;
N-acyl-L-phenylalanine;
organochlorine compound;
phenylalanine derivative		Aspergillus metabolite;
calcium channel blocker;
carcinogenic agent;
mycotoxin;
nephrotoxin;
Penicillium metabolite;
teratogenic agent
ergosterol
[no description available]		2.52203beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite
resveratrol
trans-resveratrol : A resveratrol in which the double bond has E configuration.		2.5320resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
tacrolimus
Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.		2.2110macrolide lactambacterial metabolite;
immunosuppressive agent
dactinomycin
Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)		1.9910actinomycinmutagen
glycosides
[no description available]		2.2510
stilbenes
Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.		2.5320stilbene
sesquiterpenes
[no description available]		2.2510
fumonisin b1
fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.		9.29180diester;
fumonisin;
primary amino compound;
triol		carcinogenic agent;
metabolite
fumonisin b2
fumonisin B2: produced by Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting ability. fumonisin B2 : A fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with R configuration in each case).		3.1350diester;
diol;
fumonisin;
primary amino compound		Aspergillus metabolite;
carcinogenic agent
zeranol
Zeranol: A non-steroidal estrogen analog.		3.240macrolide
valinomycin
Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.		3.9940cyclodepsipeptide;
macrocycle		antimicrobial agent;
antiviral agent;
bacterial metabolite;
potassium ionophore
u 0126
U 0126: protein kinase kinase inhibitor; structure in first source		2.1310aryl sulfide;
dinitrile;
enamine;
substituted aniline		antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
osteogenesis regulator;
vasoconstrictor agent
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
[no description available]		2.0210
mtt formazan
MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes		2.4420
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		2.1310
sterigmatocystin
[no description available]		7.4820sterigmatocystinsmetabolite
zeaxanthin
Zeaxanthins: Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA.		2.6320carotenolantioxidant;
bacterial metabolite;
cofactor
tentoxin
tentoxin: cyclic peptide from fungus Alternaria tenuis Auct.; structure		2.2510lactam
lutein
Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.		2.6320carotenolfood colouring;
plant metabolite
zearalenone
Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.		3.88110macrolide;
resorcinols		fungal metabolite;
mycoestrogen
barium
Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.		6.9510alkaline earth metal atom;
elemental barium
strontium
Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.		2.0810alkaline earth metal atom
lasalocid
Lasalocid: Cationic ionophore antibiotic obtained from Streptomyces lasaliensis that, among other effects, dissociates the calcium fluxes in muscle fibers. It is used as a coccidiostat, especially in poultry.. lasalocid : A polyether antibiotic used for prevention and treatment of coccidiosis in poultry.		6.9510beta-hydroxy ketone;
monocarboxylic acid;
monohydroxybenzoic acid;
oxanes;
oxolanes;
polyether antibiotic;
secondary alcohol;
tertiary alcohol		bacterial metabolite;
coccidiostat;
ionophore
zearalenol
zearalenol: RN given refers to (3S-(3R*,7S*,11E))-isomer		8.240
hygromycin a
hygromycin A: a cinnamide derivative produced by Streptomyces hygroscopicus; structure differs from HYGROMYCIN B		210hydroxycinnamic acidmetabolite
asteltoxin
asteltoxin: polyenic alpha-pyrone mycotoxin closely related to aurovertins isolated from Aspergillus stellatus; structure given in first source		2.1110furofuran
fusaproliferin
fusaproliferin: isolated from Fusarium proliferatum; structure in first source		6.23180
sq-23377
Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.		2.3720cyclic ether;
enol;
polyunsaturated fatty acid;
very long-chain fatty acid		calcium ionophore;
metabolite
formazans
Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.		2.4420
cereulide
cereulide: a cyclic dodecadepsipeptide; isolated from Bacillus cereus; a HEp-2 cell-vacuolation factor		7.1310
15-acetyldeoxynivalenol
15-acetyldeoxynivalenol : A trichothecene mycotoxin that is deoxynivalenol acetylated on the oxygen at C-15. A skin and eye irritant, along with its 3-acetyl regioisomer and its parent deoxynivalenol it is considered among the most commonly and widely distributed cereal contaminants.		2.1310trichotheceneepitope;
mycotoxin
virginiamycin
Virginiamycin: A cyclic polypeptide antibiotic complex from Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. It consists of 2 major components, VIRGINIAMYCIN FACTOR M1 and virginiamycin Factor S1. It is used to treat infections with gram-positive organisms and as a growth promoter in cattle, swine, and poultry.. virginiamycin : A mixture of cyclic polypeptide streptogramin antibiotics produced by Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. The two major components are virginiamycin M1 (also known as pristinamycin IIA) and virginiamycin S1. Virginiamycin has been widely used as a growth promotion agent in livestock and has been to have bacteriostatic activity against Gram-positive organisms such as staphylococci and streptococci.		6.9510
glycoursodeoxycholic acid
glycoursodeoxycholic acid : A bile acid glycine conjugate derived from ursoodeoxycholic acid.. glycoursodeoxycholate : A N-acylglycinate that is the conjugate base of glycoursodeoxycholic acid. obtained by deprotonation of the carboxy group; major species at pH 7.3.		210bile acid glycine conjugate;
N-acylglycine		human blood serum metabolite;
neuroprotective agent
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		2.0210organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
cytochrome c-t
Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.		2.7330
oligonucleotides
[no description available]		6.9910
hygromycin b
[no description available]		210
piperidines
Piperidines: A family of hexahydropyridines.		1.9510
citrinin
Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.		2.0510
deoxynivalenol-3-glucoside
deoxynivalenol-3-glucoside: a major conjugate of deoxynivalenol in beer and some brewing intermediates		2.1710trichothecene
oligomycins
Oligomycins: A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).		2.1710
bassianolide
bassianolide: cyclodepsipeptide from mycelia of Beauveria bassiana; inhibits isotonic contractions induced by acetylcholine. bassianolide : A cyclodepsipeptide consisting of a cyclic tetramer of the depsipeptide D-Hiv-N-methyl-L-leucine (where D-Hiv = D-alpha-hydroxyisovaleric acid). Found in the fungal species Beauveria bassiana and Verticillium lecanii, it has insecticidal properties and is used as a commercial biopesticide to control of insects of agricultural, veterinary and medical significance. For elucidation of the structure, see Suzuki et al., Tetrahedron Lett. 1977 v25, 2167-2170.		3.3560cyclodepsipeptide;
cyclooctadepsipeptide		antineoplastic agent;
fungal metabolite;
insecticide
fumonisin b3
fumonisin B3: structure given in first source; produced by Fusarium moniliforme		210
t-2 toxin
T-2 Toxin: A potent mycotoxin produced in feedstuffs by several species of the genus FUSARIUM. It elicits a severe inflammatory reaction in animals and has teratogenic effects.. T-2 toxin : A trichothecene mycotoxin produced by fungi of the genus Fusarium. It is a common contaminant in food and feedstuffs of cereal origin and is known to cause a range of toxic effects in humans and animals.		8.77100
ht-2 toxin
HT-2 toxin : A trichothecene mycotoxin that is T-2 toxin in which the acetyloxy group at position 4S has been hydrolysed to the corresponding hydroxy group. It is the major metabolite of T-2 toxin.		3.1750
nonactin
nonactin: macrolide tetrolide antibiotic isolated from cycloheximide-producing species of Streptomyces; minor descriptor (75-86); on-line & INDEX MEDICUS search ANTIBIOTICS (75-86)		1.9710
trypan blue
Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.7830
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Weight Gain
Increase in BODY WEIGHT over existing weight.		02.3110
2019 Novel Coronavirus Disease
[description not available]		02.4110
Liver Dysfunction
[description not available]		02.4110
Liver Diseases
Pathological processes of the LIVER.		02.4110
Benign Neoplasms
[description not available]		02.8230
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.		02.8230
Hepatocellular Carcinoma
[description not available]		07.5920
Cancer of Liver
[description not available]		02.5920
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.5920
Liver Neoplasms
Tumors or cancer of the LIVER.		02.5920
Bone Cancer
[description not available]		02.610
Osteogenic Sarcoma
[description not available]		02.610
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.610
Osteosarcoma
A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)		07.610
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.2110
Extravascular Hemolysis
[description not available]		02.2110
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.2110
Malignant Melanoma
[description not available]		02.2510
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)		02.2510
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.7930
Cancer of Pancreas
[description not available]		02.2510
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.2510
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.7230
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.9740
Innate Inflammatory Response
[description not available]		02.0810
Colitis
Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.		07.0810
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.		02.0810
Dirofilariasis
Infection with nematodes of the genus DIROFILARIA, usually in animals, especially dogs, but occasionally in man.		02.1310
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.730
Carcinoma, Non-Small Cell Lung
[description not available]		02.4620
Cancer of Lung
[description not available]		02.4620
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.4620
Lung Neoplasms
Tumors or cancer of the LUNG.		02.4620
Adenocarcinoma, Basal Cell
[description not available]		02.1310
Cancer of Colon
[description not available]		02.1310
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.1310
Colonic Neoplasms
Tumors or cancer of the COLON.		02.1310
Fungal Diseases
[description not available]		02.4720
Mycoses
Diseases caused by FUNGI.		02.4720
Acute Liver Injury, Drug-Induced
[description not available]		02.1510
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.1510
Adenoma, beta-Cell
[description not available]		02.0510
Insulinoma
A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.		02.0510
Abnormalities, Autosome
[description not available]		02.0510
Chromosome-Defective Micronuclei
[description not available]		02.0510
Disseminated Fusariosis
[description not available]		02.0810
Fusariosis
OPPORTUNISTIC INFECTIONS with the soil fungus FUSARIUM. Typically the infection is limited to the nail plate (ONYCHOMYCOSIS). The infection can however become systemic especially in an IMMUNOCOMPROMISED HOST (e.g., NEUTROPENIA) and results in cutaneous and subcutaneous lesions, fever, KERATITIS, and pulmonary infections.		02.0810
Acute Lymphoid Leukemia
[description not available]		02.0210
Precursor Cell Lymphoblastic Leukemia-Lymphoma
A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.		02.0210
Genetic Predisposition
[description not available]		02.0210
Leukemia, Lymphocytic
[description not available]		02.0310
Leukemia, Lymphoid
Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.		02.0310
Cancer of Prostate
[description not available]		02.0310
Invasiveness, Neoplasm
[description not available]		02.0310
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0310
Edema, Pulmonary
[description not available]		01.9810
Swine Diseases
Diseases of domestic swine and of the wild boar of the genus Sus.		01.9810
Pulmonary Edema
Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.		01.9810
Cholangiocellular Carcinoma
[description not available]		01.9910
Bile Duct Cancer
[description not available]		01.9910
Bile Duct Neoplasms
Tumors or cancer of the BILE DUCTS.		01.9910
Cholangiocarcinoma
A malignant tumor arising from the epithelium of the BILE DUCTS.		01.9910
EHS Tumor
[description not available]		0210
Cell Transformation, Viral
An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.		0210
Glial Cell Tumors
[description not available]		02.0110
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)		02.0110