Compounds > cucurbitacin d
Page last updated: 2024-11-10

cucurbitacin d

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Description

cucurbitacin D: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cucurbitacin D : A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23. [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 CID5281318
CHEMBL ID493646
CHEBI ID3943
SCHEMBL ID230654
MeSH IDM0114857

Synonyms (37)

Synonym
19-norlanosta-5,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23e)-
19-nor-9.beta.,23-diene-3,11,22-trione, 9-methyl-2.beta.,16.alpha.,20,25-tetrahydroxy-
nsc-308606
cucurbitacine (d)
NSC308606 ,
elatericin a
LMST01010106
nsc 521776
elatericine a
19-norlanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23e)-
nsc 308606
19-nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-
nsc-521776
nsc521776
C08796
3877-86-9
cucurbitacin d
(23e)-2beta,16alpha,20,25-tetrahydroxy-10alpha-cucurbita-5,23-diene-3,11,22-trione
(2s,4r,23e)-2,16,20,25-tetrahydroxy-9beta,10,14-trimethyl-4,9-cyclo-9,10-seco-16alpha-cholesta-5,23-diene-1,11,22-trione
CHEBI:3943 ,
(23e)-2beta,16alpha,20,25- tetrahydroxy-9beta-methyl-19-nor-10alpha-lanosta-5,23-diene-3,11,22-trione
CHEMBL493646
unii-5i62h4orc7
5i62h4orc7 ,
AKOS015896755
cucurbitacine d
19-norlanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23e)-
SCHEMBL230654
19-norlanosta-5,23-diene-3,11,22-trione,2,16,20,25-tetrahydroxy-9-methyl-, (2b,9b,10a,16a,23e)-
ncgc00385253-01_c30h44o7_(2s,4r,9beta,16alpha,23e)-2,16,20,25-tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-5,23-diene-1,11,22-trione
NCGC00385253-01
cucurbitacin d (elatericin a)
Q15410915
CS-0018307
HY-N1986
AS-79683
DTXSID401032034

Research Excerpts

Overview

Cucurbitacin D (CuD) is a natural compound that can be isolated in various plant families, mainly from Ecballium elaterium (L.) A.

ExcerptReferenceRelevance
"Cucurbitacin D (CuD) is a natural compound that can be isolated in various plant families, mainly from Ecballium elaterium (L.) A. "( Cucurbitacin D Inhibits the Proliferation of HepG2 Cells and Induces Apoptosis by Modulating JAK/STAT3, PI3K/Akt/mTOR and MAPK Signaling Pathways.
Baysar, A; Çiğremiş, Y; Durhan, M; Mehdi Üremiş, M; Tosun, E; Türköz, Y; Üremiş, N, 2022)		3.61

Actions

ExcerptReferenceRelevance
"Cucurbitacin D could increase LPS-induced interleukin (IL)-1β production in culture supernatant of THP-1 cells, peritoneal exudate cells (PECs), bone marrow derived macrophages (BMDMs), and RAW264 cells."( Cucurbitacin D is a new inflammasome activator in macrophages.
Ding, N; Kanazawa, T; Song, Y; Yamashita, U; Yoshida, Y, 2013)		2.55

Treatment

ExcerptReferenceRelevance
"Cucurbitacin D treatment of cervical cancer cells arrested the cell cycle in G1/S phase, inhibited constitutive expression of E6, Cyclin D1, CDK4, pRb, and Rb and induced the protein levels of p21 and p27."( Cucurbitacin D exhibits potent anti-cancer activity in cervical cancer.
Alsayari, A; Chauhan, SC; Hafeez, BB; Halaweish, FT; Jaggi, M; Malik, S; Sikander, M; Yallapu, MM, 2016)		2.6

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
cucurbitacinAny one of a class of tetracyclic triterpenoids, formally derived from the triterpene hydrocarbon cucurbitane, developed by some plants (especially those of the family Cucurbitaceaeas) as a defence mechanism against herbivores.
secondary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
tertiary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Integrin alpha-LHomo sapiens (human)IC50 (µMol)1.36000.00080.60203.7800AID337982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
T cell activation via T cell receptor contact with antigen bound to MHC molecule on antigen presenting cellIntegrin alpha-LHomo sapiens (human)
phagocytosisIntegrin alpha-LHomo sapiens (human)
inflammatory responseIntegrin alpha-LHomo sapiens (human)
cell adhesionIntegrin alpha-LHomo sapiens (human)
heterophilic cell-cell adhesion via plasma membrane cell adhesion moleculesIntegrin alpha-LHomo sapiens (human)
leukocyte cell-cell adhesionIntegrin alpha-LHomo sapiens (human)
cell-matrix adhesionIntegrin alpha-LHomo sapiens (human)
signal transductionIntegrin alpha-LHomo sapiens (human)
integrin-mediated signaling pathwayIntegrin alpha-LHomo sapiens (human)
memory T cell extravasationIntegrin alpha-LHomo sapiens (human)
receptor clusteringIntegrin alpha-LHomo sapiens (human)
cell-cell adhesionIntegrin alpha-LHomo sapiens (human)
cell adhesion mediated by integrinIntegrin alpha-LHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingIntegrin alpha-LHomo sapiens (human)
ICAM-3 receptor activityIntegrin alpha-LHomo sapiens (human)
metal ion bindingIntegrin alpha-LHomo sapiens (human)
cell adhesion molecule bindingIntegrin alpha-LHomo sapiens (human)
integrin bindingIntegrin alpha-LHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneIntegrin alpha-LHomo sapiens (human)
cell surfaceIntegrin alpha-LHomo sapiens (human)
membraneIntegrin alpha-LHomo sapiens (human)
integrin alphaL-beta2 complexIntegrin alpha-LHomo sapiens (human)
specific granule membraneIntegrin alpha-LHomo sapiens (human)
extracellular exosomeIntegrin alpha-LHomo sapiens (human)
integrin complexIntegrin alpha-LHomo sapiens (human)
external side of plasma membraneIntegrin alpha-LHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (45)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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.
AID1225618Inhibition of HSP90 in human MCF7 cells assessed as Raf degradation after 24 hrs by Western blot analysis2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1197350Cytotoxicity against human Bel7402 cells assessed as growth inhibition2015European journal of medicinal chemistry, Mar-06, Volume: 92Medicinal uses, phytochemistry and pharmacology of family Sterculiaceae: a review.
AID592724Hepatoprotective activity in human HepG2 cells assessed as protection against cell damage after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID592715Hepatoprotective activity in human HepG2 cells assessed as inhibition of CCl4-induced toxicity after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID1225628Inhibition of HSP90 in human MCF7 cells assessed as disruption of interaction with Cdc37 at 5 times IC50 after 24 hrs by co-immunoprecipitation assay2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID398034Cytotoxicity against human MCF7 cells2003Journal of natural products, Nov, Volume: 66, Issue:11
Cytotoxic cucurbitacin constituents from Sloanea zuliaensis.
AID1225613Inhibition of HSP90 in human MCF7 cells assessed as induction of heat shock response-mediated HSP70 production at 5 times IC50 after 24 hrs by Western blot analysis relative to vehicle-treated control2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225629Inhibition of HSP90 in human MCF7 cells assessed as disruption of interaction with p23 at 5 times IC50 after 24 hrs by co-immunoprecipitation assay2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID337982Inhibition of LFA1 expressed in human JY cells interaction with ICAM1-IG expressed in human HeLa cell monolayer after 45 mins by cell adhesion assay1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID592718Ratio of IC50 to EC50 for hepatoprotective activity in human HepG2 cells2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID592721Cytotoxicity against rat HSC-T6 cell after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID337983Cytotoxicity against human JY cells assessed as inhibition of thymidine uptake at 0.3 uM by scintillation counting1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID1225620Change in p23 expression in human MCF7 cells at 0.01 to 10 uM after 24 hrs by Western blot analysis2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID337984Cytotoxicity against human JY cells assessed as inhibition of thymidine uptake at 1 uM by scintillation counting1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID1225617Inhibition of HSP90 in human MCF7 cells assessed as Cdk6 degradation after 24 hrs by Western blot analysis2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1197349Cytotoxicity against human SK-MEL-28 cells assessed as growth inhibition2015European journal of medicinal chemistry, Mar-06, Volume: 92Medicinal uses, phytochemistry and pharmacology of family Sterculiaceae: a review.
AID1225619Change in Cdc37 expression in human MCF7 cells at 0.01 to 10 uM after 24 hrs by Western blot analysis2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225615Inhibition of HSP90 in human MCF7 cells assessed as pAkt degradation after 24 hrs by Western blot analysis2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID337985Cytotoxicity against human JY cells assessed as inhibition of thymidine uptake at 3.3 uM by scintillation counting1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID592722Antiproliferative activity against serum-stimulated rat HSC-T6 cells after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID337992Inhibition of actin polymerization in fMLP-stimulated human neutrophils assessed as positive fluorescence signal at 3.3 uM1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID592720Ratio of IC50 for human HepG2 cells to IC50 for human HeLa cells2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID354491Growth inhibition of human CNS cancer cells2004Journal of natural products, Aug, Volume: 67, Issue:8
An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients.
AID337993Inhibition of actin polymerization in fMLP-stimulated human neutrophils assessed as positive fluorescence signal at 0.33 uM1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID398036Cytotoxicity against human SF268 cells2003Journal of natural products, Nov, Volume: 66, Issue:11
Cytotoxic cucurbitacin constituents from Sloanea zuliaensis.
AID354488Growth inhibition of human colon cancer cells2004Journal of natural products, Aug, Volume: 67, Issue:8
An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients.
AID659254Cytotoxicity against human HT-29 cells after 3 days by mitochondrial transmembrane potential assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Isolation, structure elucidation, and biological evaluation of 16,23-epoxycucurbitacin constituents from Eleaocarpus chinensis.
AID1225612Inhibition of HSP90 in human MCF7 cells assessed as induction of heat shock response-mediated HSP90 production at 5 times IC50 after 24 hrs by Western blot analysis relative to vehicle-treated control2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225632Inhibition of HSP90 in human MCF7 cells assessed as induction of heat shock response-mediated HSP27 production at 5 times to 10 times IC50 after 24 hrs by Western blot analysis relative to vehicle-treated control2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID354489Growth inhibition of human breast cancer cells2004Journal of natural products, Aug, Volume: 67, Issue:8
An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients.
AID1225605Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs by MTS/PMS assay2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID380252Antiproliferative activity against human NCI-H460 cells after 72 hrs2006Journal of natural products, Dec, Volume: 69, Issue:12
Cucurbitane triterpenes from the fruiting bodies and cultivated mycelia of Leucopaxillus gentianeus.
AID659253Cytotoxicity against human HT-29 cells after 3 days by sulforhodamine B assay2012Journal of natural products, Mar-23, Volume: 75, Issue:3
Isolation, structure elucidation, and biological evaluation of 16,23-epoxycucurbitacin constituents from Eleaocarpus chinensis.
AID1225616Inhibition of HSP90 in human MCF7 cells assessed as Her2 degradation after 24 hrs by Western blot analysis2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID337991Inhibition of actin polymerization in fMLP-stimulated human neutrophils assessed as positive fluorescence signal at 1 uM1994Journal of natural products, Nov, Volume: 57, Issue:11
Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
AID592714Cytotoxicity against human HepG2 cells after 24 hrs assessed as inhibition of cell viability by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID354490Growth inhibition of human lung cancer cells2004Journal of natural products, Aug, Volume: 67, Issue:8
An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients.
AID398035Cytotoxicity against human H460 cells2003Journal of natural products, Nov, Volume: 66, Issue:11
Cytotoxic cucurbitacin constituents from Sloanea zuliaensis.
AID592723Ratio of IC50 to EC50 for antiproliferative activity in rat HSC-T6 cells2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID592719Cytotoxicity against human HeLa cells after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (5.00)18.7374
1990's3 (7.50)18.2507
2000's11 (27.50)29.6817
2010's18 (45.00)24.3611
2020's6 (15.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.73

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 Index24.73 (24.57)
Research Supply Index3.71 (2.92)
Research Growth Index5.11 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other38 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.13106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
benzoic acid
Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.		2.0510benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
tocopheroxy radical
tocopheroxy radical: RN given refers to radical ion (1+), (2R-(2R*(4R*,8R*)))-isomer; RN for cpd without isomeric designation not available 12/90		3.2110tocopherol
phenylbutazone
Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.		2.0610pyrazolidinesantirheumatic drug;
EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor;
metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug
carbon tetrachloride
Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.		2.0610chlorocarbon;
chloromethanes		hepatotoxic agent;
refrigerant
chloramphenicol
Amphenicol: Chloramphenicol and its derivatives.		3.2110C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor
deoxycytidine
[no description available]		2.2110pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
mansonone c
mansonone C: structure in first source		3.21101,2-naphthoquinones;
sesquiterpenoid
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0710taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.0610chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
topotecan
Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.		2.0310pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		2.2110organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
epicatechin
(-)-epicatechin : A catechin with (2R,3R)-configuration.		3.2110catechin;
polyphenol		antioxidant
beta-peltatin
beta-peltatin : An organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted into the corresponding methyl ether.		3.1210furonaphthodioxole;
gamma-lactone;
lignan;
organic heterotetracyclic compound;
phenols		antineoplastic agent;
plant metabolite
sn 38
SN-38 : A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.		2.0310delta-lactone;
phenols;
pyranoindolizinoquinoline;
tertiary alcohol		antineoplastic agent;
apoptosis inducer;
drug metabolite;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
cucurbitacins
[no description available]		2.753011-oxo steroid
celastrol
[no description available]		2.1110monocarboxylic acid;
pentacyclic triterpenoid		anti-inflammatory drug;
antineoplastic agent;
antioxidant;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
Hsp90 inhibitor;
metabolite
procyanidin b2
procyanidin B2 : A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8' in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.		3.2110biflavonoid;
hydroxyflavan;
polyphenol;
proanthocyanidin		antioxidant;
metabolite
procyanidin b5
procyanidin B5 : A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 6' in beta-configuration. It can be found in grape seeds, in Hibiscus cannabinus (kenaf) root and bark, in apple and in cacao.		3.2110biflavonoid;
hydroxyflavan;
polyphenol;
proanthocyanidin		metabolite
procyanidin C1
procyanidin trimer C1: a flavonoid found in multiple plant sources including grape, apple, and cacao, which has antioxidant and anti-inflammatory properties. procyanidin C1 : A proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages.		3.2110hydroxyflavan;
polyphenol;
proanthocyanidin		anti-inflammatory agent;
antioxidant;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
lipoxygenase inhibitor;
metabolite
cucurbitacin r
cucurbitacin R: from Cayaponia tayuya roots; structure in first source. 23,24-dihydrocucurbitacin D : A 23,24-dihydrocucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at position 5.		1.981023,24-dihydrocucurbitacin;
secondary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone
lanosterol
[no description available]		1.961014alpha-methyl steroid;
3beta-sterol;
tetracyclic triterpenoid		bacterial metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
23,24-dihydrocucurbitacin b
23,24-dihydrocucurbitacin B: from the leaves of Morierina montana Vieill; structure in first source. 23,24-dihydrocucurbitacin B : A 23,24-dihydrocucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at position 5; a hydroxy function at C-25 is acetylated.		2.111023,24-dihydrocucurbitacin;
secondary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone
anthricin
anthricin: antitumor constituent from Anthriscus sylvestris (L.) Hoffm; structure in first source. deoxypodophyllotoxin : A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group.		3.1210furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes		antineoplastic agent;
apoptosis inducer;
plant metabolite
cucurbitacin f
cucurbitacin F: structure in first source		2.0110
gamma-sitosterol
clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.		2.06103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite
mansonone g
[no description available]		3.2110
glycosides
[no description available]		2.5220
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		2.0610
silybin
[no description available]		2.0610
quercetin
[no description available]		2.06107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
bilirubin
[no description available]		2.0310biladienes;
dicarboxylic acid		antioxidant;
human metabolite;
mouse metabolite
cucurbitacin b
[no description available]		3.1350cucurbitacin;
secondary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone
cucurbitacin c
cucurbitacin C: structure in first source		2.0510cucurbitacin
nsc 106399
cucurbitacin E: RN refers to (9beta,10alpha,16alpha,23E)-isomer; structure given in first source. cucurbitacin E : A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23.		4.3860cucurbitacin;
tertiary alpha-hydroxy ketone
cucurbitacin i
cucurbitacin I: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins. cucurbitacin I : A cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22.		4.6280cucurbitacin;
tertiary alpha-hydroxy ketone		antineoplastic agent;
plant metabolite
ellagic acid
[no description available]		2.0110catechols;
cyclic ketone;
lactone;
organic heterotetracyclic compound;
polyphenol		antioxidant;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor;
EC 2.4.1.1 (glycogen phosphorylase) inhibitor;
EC 2.5.1.18 (glutathione transferase) inhibitor;
EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor;
EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor;
EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
food additive;
fungal metabolite;
geroprotector;
plant metabolite;
skin lightening agent
geldanamycin
[no description available]		2.11101,4-benzoquinones;
ansamycin;
carbamate ester;
organic heterobicyclic compound		antimicrobial agent;
antineoplastic agent;
antiviral agent;
cysteine protease inhibitor;
Hsp90 inhibitor
cytochalasin b
Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.		1.9810cytochalasin;
lactam;
lactone;
organic heterotricyclic compound		actin polymerisation inhibitor;
metabolite;
mycotoxin;
platelet aggregation inhibitor
furanoheliangolide
furanoheliangolide: structure in first source		2.0810
geldanamycin
[no description available]		2.1110
ecdysterone
Ecdysterone: A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. Ecdysterone is the 20-hydroxylated ECDYSONE.. 20-hydroxyecdysone : An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.		1.991014alpha-hydroxy steroid;
20-hydroxy steroid;
22-hydroxy steroid;
25-hydroxy steroid;
2beta-hydroxy steroid;
3beta-sterol;
ecdysteroid;
phytoecdysteroid		animal metabolite;
plant metabolite
pyracrenic acid
pyracrenic acid: a lupane from bark of Pyracantha crenulata; structure given in first source		3.5920triterpenoidmetabolite
cucurbitacin I 2-O-beta-D-glucopyranoside
cucurbitacin I 2-O-beta-D-glucopyranoside : A triterpenoid saponin that is cucurbitacin I attached to a beta-D-glucopyranosyl residue at position 2 via a glycosidic linkage. It has been isolated from Machilus yaoshansis.		2.0610beta-D-glucoside;
cucurbitacin;
monosaccharide derivative;
tertiary alpha-hydroxy ketone;
triterpenoid saponin		plant metabolite
bryonolic acid
bryonolic acid: structure given in first source; an anti-allergy agent isolated from Luffa cylindrica, the roots of Bryonia dioica, and the fruit hulls of Sandrica indicum		2.0510
gedunin
[no description available]		2.1110acetate ester;
enone;
epoxide;
furans;
lactone;
limonoid;
organic heteropentacyclic compound;
pentacyclic triterpenoid		antimalarial;
antineoplastic agent;
Hsp90 inhibitor;
plant metabolite
cinnamtannin a2
cinnamtannin A2: a tetrameric proanthcyanidin; isolated from cacao products; structure in first source. cinnamtannin A2 : A proanthocyanidin isolated from Cinnamomum cassia.		3.2110proanthocyanidinplant metabolite
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0610ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
cucurbitane
cucurbitane: structure in first source. cucurbitane : A triterpene that is an isomer of lanostane obtained by migration of the methyl group from 10 to the 9beta position.		2.5220triterpene
3-methyladenine
N3-methyladenine: structure in first source		2.1310
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		2.2510nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
pemetrexed
pemetrexed disodium : An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).		2.2510N-acyl-L-glutamic acid;
pyrrolopyrimidine		antimetabolite;
antineoplastic agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
EC 2.1.1.45 (thymidylate synthase) inhibitor;
EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.4520
Cancer of Lung
[description not available]		02.7730
Central Nervous System Neoplasm
[description not available]		02.0110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.4520
Lung Neoplasms
Tumors or cancer of the LUNG.		02.7730
Central Nervous System Neoplasms
Benign and malignant neoplastic processes that arise from or secondarily involve the brain, spinal cord, or meninges.		02.0110
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.9310
Cirrhosis
[description not available]		02.0610
Fibrosis
Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.		02.0610
Benign Neoplasms
[description not available]		02.1110
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.		02.1110
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.		02.6320
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
Hepatocellular Carcinoma
[description not available]		07.5220
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.		02.5220
Carcinoma, Non-Small Cell Lung
[description not available]		02.5520
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.		02.5520
Cancer of Pancreas
[description not available]		02.2110
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).		02.2110
ATLL
[description not available]		02.5320
Leukemia-Lymphoma, Adult T-Cell
Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.		02.5320
Cancer of Stomach
[description not available]		02.1710
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.1710
Benign Meningeal Neoplasms
[description not available]		02.0810
Angioblastic Meningioma
[description not available]		02.0810
Neurilemoma
[description not available]		02.0810
Meningeal Neoplasms
Benign and malignant neoplastic processes that arise from or secondarily involve the meningeal coverings of the brain and spinal cord.		02.0810
Meningioma
A relatively common neoplasm of the CENTRAL NERVOUS SYSTEM that arises from arachnoidal cells. The majority are well differentiated vascular tumors which grow slowly and have a low potential to be invasive, although malignant subtypes occur. Meningiomas have a predilection to arise from the parasagittal region, cerebral convexity, sphenoidal ridge, olfactory groove, and SPINAL CANAL. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2056-7)		07.0810
Neurilemmoma
A neoplasm that arises from SCHWANN CELLS of the cranial, peripheral, and autonomic nerves. Clinically, these tumors may present as a cranial neuropathy, abdominal or soft tissue mass, intracranial lesion, or with spinal cord compression. Histologically, these tumors are encapsulated, highly vascular, and composed of a homogenous pattern of biphasic fusiform-shaped cells that may have a palisaded appearance. (From DeVita Jr et al., Cancer: Principles and Practice of Oncology, 5th ed, pp964-5)		02.0810
Leukemia, Lymphocytic, T Cell
[description not available]		02.1310
Leukemia, T-Cell
A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.		02.1310
Cancer of Cervix
[description not available]		02.1310
Uterine Cervical Neoplasms
Tumors or cancer of the UTERINE CERVIX.		02.1310
Cancer of Liver
[description not available]		02.0510
Liver Neoplasms
Tumors or cancer of the LIVER.		02.0510
Cancer of Ovary
[description not available]		02.0810
Cancer of Endometrium
[description not available]		02.0810
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.0810
Endometrial Neoplasms
Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.		02.0810
Malignant Melanoma
[description not available]		02.0110
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.0110
Bilirubinemia
[description not available]		02.0310
Food Poisoning
[description not available]		01.9610