Compounds > alpha-toxicarol
Page last updated: 2024-11-08

alpha-toxicarol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

alpha-toxicarol: from the roots of Derris trifoliata; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
DerrisgenusA plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID442826
CHEMBL ID508992
CHEBI ID9643
SCHEMBL ID4742046
MeSH IDM0485861

Synonyms (9)

Synonym
alpha-toxicarol
toxicarol
CHEMBL508992
chebi:9643 ,
LMPK12060027
SCHEMBL4742046
AKOS032949012
(1s,14s)-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
Q27108457
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoflavanonesMembers of the class of isoflavans that have a 3,4-dihydro-3-aryl-2H-1-benzopyran-4-one skeleton and its substituted derivatives.
[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)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Quinone oxidoreductaseMus musculus (house mouse)CD23.00000.20002.74219.8000AID356395
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID356393Inhibition of mouse Hepa-1c1c7 cells by MTT assay2003Journal of natural products, Sep, Volume: 66, Issue:9
Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.
AID334261Antibacterial activity against Bacteroides fragilis ATCC 25285 at 625 ug/mL after 24 hrs by conventional well agar method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID356392Inhibition of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary gland culture at 10 ug/mL2003Journal of natural products, Sep, Volume: 66, Issue:9
Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.
AID334260Antibacterial activity against Micrococcus luteus ATCC 9341 at 625 ug/mL after 24 hrs by conventional well agar method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID1083032Insecticidal activity against adult Callosobruchus maculatus assessed mean survival fraction ratio at 100 ppm measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction)2012Journal of agricultural and food chemistry, Oct-10, Volume: 60, Issue:40
Highly variable insect control efficacy of Tephrosia vogelii chemotypes.
AID334263Antibacterial activity against Pseudomonas aeruginosa ATCC 9027 at 625 ug/mL after 24 hrs by conventional well agar method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID356394Chemoprevention index, ratio of IC50 for mouse Hepa-1c1c7 cells to drug level required to double NADPH:quinone reductase activity in mouse Hepa-1c1c7 cells2003Journal of natural products, Sep, Volume: 66, Issue:9
Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.
AID1083031Insecticidal activity against adult Callosobruchus maculatus assessed mean survival fraction ratio at 10 ppm measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction)2012Journal of agricultural and food chemistry, Oct-10, Volume: 60, Issue:40
Highly variable insect control efficacy of Tephrosia vogelii chemotypes.
AID1437927Cytotoxicity against mouse L5178Y cells by MTT assay2017Journal of natural products, 01-27, Volume: 80, Issue:1
Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa.
AID1083030Insecticidal activity against adult Callosobruchus maculatus assessed reduction mean survival fraction measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction)2012Journal of agricultural and food chemistry, Oct-10, Volume: 60, Issue:40
Highly variable insect control efficacy of Tephrosia vogelii chemotypes.
AID1083033Insecticidal activity against adult Callosobruchus maculatus assessed mean survival fraction ratio at 500 ppm measured 72 hr post dose (Rvb = 4.4 +/- 0.31 mean survival fraction)2012Journal of agricultural and food chemistry, Oct-10, Volume: 60, Issue:40
Highly variable insect control efficacy of Tephrosia vogelii chemotypes.
AID334262Antibacterial activity against Escherichia coli ATCC 10536 at 625 ug/mL after 24 hrs by conventional well agar method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID334264Antifungal activity against Candida albicans ATCC 10231 at 625 ug/mL after 24 hrs by conventional well agar method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID356395Induction of NADPH:quinone reductase in mouse Hepa-1c1c7 cells assessed as drug level required to double enzyme activity by MTT assay2003Journal of natural products, Sep, Volume: 66, Issue:9
Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.
AID334259Antibacterial activity against Bacillus subtilis ATCC 6633 at 625 ug/mL after 24 hrs by conventional well agar method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID334258Antibacterial activity against Helicobacter pylori 31A after 48 hrs by serial doubling dilution method2002Journal of natural products, Apr, Volume: 65, Issue:4
Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's3 (42.86)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
sulforaphane
sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.		2.0110isothiocyanate;
sulfoxide		antineoplastic agent;
antioxidant;
EC 3.5.1.98 (histone deacetylase) inhibitor;
plant metabolite
rotenone
Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.		3.150organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
mitochondrial NADH:ubiquinone reductase inhibitor;
phytogenic insecticide;
piscicide;
toxin
rotenolone
rotenolone: decomposition product of rotenone; RN given refers to (2 alpha,6a beta,12a beta)-isomer		2.0110organic molecular entitymetabolite
clarithromycin
Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.		2.0110macrolide antibioticantibacterial drug;
environmental contaminant;
protein synthesis inhibitor;
xenobiotic
deguelin
deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.		2.9640aromatic ether;
diether;
organic heteropentacyclic compound;
rotenones		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
mitochondrial NADH:ubiquinone reductase inhibitor;
plant metabolite
tephrosin
tephrosin: RN given for (7aR-cis)-isomer; has insecticidal activity; structure in first source. tephrosin : A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities.		2.4420aromatic ether;
cyclic ketone;
organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
pesticide
moxifloxacin
Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.		2.1510aromatic ether;
cyclopropanes;
fluoroquinolone antibiotic;
pyrrolidinopiperidine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug
elliptone
[no description available]		2.0110
isoliquiritigenin
[no description available]		2.0110chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
xanthoangelol
xanthoangelol: from Angelica keiskei; structure given in first source; RN given refers to (E,E)-isomer		2.1510
Dehydrodeguelin,7a,13a-Didehydrodeguelin
[no description available]		2.4620rotenones
chrysoeriol
chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.		2.0110monomethoxyflavone;
trihydroxyflavone		antineoplastic agent;
antioxidant;
metabolite
genistein
[no description available]		2.01107-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
amorphastilbol
amorphastilbol: dual PPARalpha/gamma agonist from Amorpha species		2.1510
(6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-[1]benzopyrano[3,4-b][1]benzopyran-12-one
[no description available]		2.1510rotenones
amorfrutin a
amorfrutin A: an antidiabetic agent that inhibits NF-kappaB activation; structure in first source		2.1510stilbenoid
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatocellular Carcinoma
[description not available]		02.0110
Experimental Mammary Neoplasms
[description not available]		02.0110
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.		02.0110
Benign Neoplasms
[description not available]		03.0310
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.0310
Germinoblastoma
[description not available]		02.1510
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.1510