Compounds > sampangine
Page last updated: 2024-11-08

sampangine

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Description

sampangine: a plant-derived copyrine alkaloid extracted from the stem bark of Cananga odorata [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

sampangine : A copyrine alkaloid with formula C15H8N2O, extracted from several plants including the stem bark of Cananga odorata. It is a heme biosynthesis inhibitor and exhibits antifungal and anticancer properties. [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]

FloraRankFlora DefinitionFamilyFamily Definition
CanangagenusA plant genus of the family ANNONACEAE known for its aromatic oil (OILS, VOLATILE).[MeSH]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]
Cananga odorataspecies[no description available]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]

Cross-References

ID SourceID
PubMed CID387195
CHEMBL ID435201
CHEBI ID67606
SCHEMBL ID6230423
MeSH IDM0334680

Synonyms (24)

Synonym
nsc-680736
1,6-diaza-benzo[de]anthracen-7-one
sampangine
nsc680736
116664-93-8
CHEMBL435201
chebi:67606 ,
7h-naphtho[1,2,3-ij][2,7]naphthyridin-7-one
f1eag7d138 ,
unii-f1eag7d138
1,6-diaza-benzo(de)anthracen-7-one
nsc 680736
BWQKHOMAOVUASZ-UHFFFAOYSA-N
sampan-gine
SCHEMBL6230423
DTXSID3041118
10,16-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,9,11,13,15-octaen-8-one
bdbm50478733
7h-naphtho[1,2,3,-ij][2,7]naphthyridin-7-one, 9ci
Q6118076
sampangin
bc-1-21
7h-naphtho(1,2,3-ij)(2,7)naphthyridin-7-one
10,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

Research Excerpts

Overview

Sampangine is a plant-derived antifungal copyrine alkaloid extracted from the stem bark of Cananga odorata.

ExcerptReferenceRelevance
"Sampangine (1) is a plant-derived antifungal copyrine alkaloid extracted from the stem bark of Cananga odorata. "( Characterization of the major metabolite of sampangine in rats.
Clark, AM; Hufford, CD; Orabi, KY; Walker, LA, 2000)		2.01
"Sampangine is a plant-derived copyrine alkaloid extracted from the stem bark of Cananga odorata. "( Induction of apoptosis by the plant alkaloid sampangine in human HL-60 leukemia cells is mediated by reactive oxygen species.
Bailly, C; Degardin, K; Kluza, J; Lansiaux, A; Mazinghien, R, 2005)		2.03
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
[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 (2)

ClassDescription
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
organic heterotetracyclic compound
[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 (70)

Assay IDTitleYearJournalArticle
AID360008Antibacterial activity against Staphylococcus aureus ATCC 6535 after 48 hrs by modified well microplate assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID380067Metabolic stability in Wistar rat urine assessed as sampangine beta-glucuronic acid levels at 80 mg/kg, ip after 24 hrs2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID360012Inhibition of LFA1/ICAM1-mediated aggregation of TPA-stimulated human HL60 cells pretreated 10 mins before TPA challenge measured after 16 hrs of PMA addition by microscopy2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID380069Antifungal activity against Cryptococcus neoformans ATCC 52657 at 100 ug/mL after 48 hrs by bioautography2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID1187445Kinetic solubility of the compound in PBS buffer at pH 7.42014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID1493828Antifungal activity against Candida parapsilosis 22019 after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID360014Specific index, ratio of IC50 for human HL60 cells to MIC for LFA1/ICAM1 mediated aggregation in TPA-stimulated human HL60 cells2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1187441Antifungal activity against Candida albicans after 24 hrs by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID1493830Antifungal activity against Cryptococcus neoformans 32609 after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID1276311Increase in oxygen consumption rate in digitonin permeabilized human T47D cells assessed as reinitiation of sodium azide-stalled cellular respiration at 30 uM relative to control2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID360010Antifungal activity against Candida albicans B3112001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1187443Antifungal activity against Trichophyton rubrum by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID605937Antiproliferative activity against human A2780 cells after 2 days by Alamar Blue assay2011Journal of natural products, May-27, Volume: 74, Issue:5
Isolation and synthesis of antiproliferative eupolauridine alkaloids of Ambavia gerrardii from the Madagascar Dry Forest.
AID1187440Antifungal activity against Cryptococcus neoformans after 72 hrs by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID1276312Induction of alteration in mitochondrial membrane potential in human T47D cells assessed as intracellular calcium level at 30 uM after 30 mins by fura-2 dye based fluorescence assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID1276328Increase in oxygen consumption rate in Saccharomyces cerevisiae at 10 to 30 uM by oxytherm Clark-type electrode assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID1187442Antifungal activity against Candida glabrata after 24 hrs by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID360002Cytotoxicity against human SK-MEL cells after 2 to 7 days by neutral red assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276323Neurotoxicity against rat CGN assessed as neuronal cell death at 30 uM after 24 hrs by Hoechst 33342/propidium iodide staining based assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID360007Antifungal activity against Cryptococcus neoformans ATCC 90113 after 48 hrs by modified well microplate assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID380071Antifungal activity against Candida albicans NIH B311 at 100 ug/mL after 24 hrs by agar well diffusion method2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID359999Selectivity index, ratio of IC50 of african green monkey (Cercopithecus aethiops) Vero cells to IC50 for chloroquine-sensitive Plasmodium falciparum D62001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276326Increase in oxygen consumption rate in human T47D cells by oxytherm Clark-type electrode assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID360004Cytotoxicity against human BT549 cells after 2 to 7 days by neutral red assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID380072Antifungal activity against Cryptococcus neoformans ATCC 52657 at 100 ug/mL after 48 hrs by agar well diffusion method2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID360013Cytotoxicity against human HL60 cells after 7 days by XTT/PMS assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276308Effect on mitochondrial membrane potential in human T47D cells at 30 uM after 30 mins by TMRM dye based fluorescence microscopy2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID359997Selectivity index, ratio of IC50 of african green monkey (Cercopithecus aethiops) Vero cells to IC50 for chloroquine-resistant Plasmodium falciparum W22001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276325Increase in oxygen consumption rate in human T47D cells at 30 uM by oxytherm Clark-type electrode assay relative to control2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID360006Antifungal activity against Candida albicans B311 after 48 hrs by modified well microplate assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276313Increase in oxygen consumption rate in digitonin permeabilized human T47D cells assessed as reinitiation of sodium azide-stalled cellular respiration by oxytherm Clark-type electrode assay in presence of ascorbate relative to compound alone2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID359996Antimalarial activity after 48 hrs against chloroquine-resistant Plasmodium falciparum W2 as LDH activity by Makler method2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID380578Antifungal activity against Candida albicans NIH B311 after 24 hrs by agar well diffusion method1999Journal of natural products, Jul, Volume: 62, Issue:7
Microbial transformation of sampangine.
AID144140In vitro anti-mycobacterial activity against Mycobacterium intracellular ATCC 23068. 1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.
AID1276321Cytostatic activity against human T47D cells at 1 to 30 uM after 48 hrs by sulforhodamine B assay in presence of ascorbate2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID1187444Antifungal activity against Microsporum gypseum by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID1493827Antifungal activity against Candida albicans SC5314 after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID380338Antifungal activity against Cryptococcus neoformans ATCC 52657 after 48 hrs by twofold serial dilution method2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID360016Specific index, ratio of IC50 for human HL60 cells to IC50 for LFA1/ICAM1-mediated CFSE-labeled TPA-stimulated human HL60 cell adhesion to ICAM1 expressing human HeLa cells2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276319Cytotoxicity against human MDA-MB-231 cells at 1 to 30 uM after 48 hrs by sulforhodamine B assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID1187438Antifungal activity against Candida parapsilosis after 24 hrs by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID1493833Antifungal activity against Microsporum gypseum Cmccfmza after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID1276307Increase in oxygen consumption rate of mitochondrial state 4 respiration in human Hep3B cells assessed as reinitiation of oligomycin-stalled cellular respiration by Clark-type oxygen electrode assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID380579Antifungal activity against Cryptococcus neoformans ATCC 52657 after 48 hrs by agar well diffusion method1999Journal of natural products, Jul, Volume: 62, Issue:7
Microbial transformation of sampangine.
AID360009Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 33591 after 48 hrs by modified well microplate assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276318Cytostatic activity against human T47D cells at 1 to 30 uM after 48 hrs by sulforhodamine B assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID380068Antifungal activity against Candida albicans NIH B311 at 100 ug/mL after 24 hrs by bioautography2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID1276320Cytostatic activity against human MDA-MB-231 cells at 1 to 30 uM after 48 hrs by sulforhodamine B assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID359998Antimalarial activity after 48 hrs against chloroquine-sensitive Plasmodium falciparum D6 as LDH activity by Makler method2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276316Activation of hypoxia-induced HIF-1 in human T47D cells cotransfected with pHRE-luciferase plasmid at 1 to 3 uM preincubated for 30 mins followed by hypoxia induction measured after 16 hrs by luciferase reporter gene assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID605938Antiproliferative activity against human H460 cells after 96 hrs by Cell Titre-Glo luminescent assay2011Journal of natural products, May-27, Volume: 74, Issue:5
Isolation and synthesis of antiproliferative eupolauridine alkaloids of Ambavia gerrardii from the Madagascar Dry Forest.
AID380066Metabolic stability in Wistar rat urine assessed as sampangine-4-O-methyl-beta-glucopyranoside levels at 80 mg/kg, ip after 24 hrs2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID1276324Increase in oxygen consumption rate in digitonin permeabilized human T47D cells at 30 uM relative to control2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID55038In vitro anti-mycobacterial activity against Cryptococcus neoformans ATCC 32264.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.
AID380065Metabolic stability in Wistar rat urine assessed as sampangine beta-glucopyranoside levels at 80 mg/kg, ip after 24 hrs2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID1187439Antifungal activity against Aspergillus fumigatus after 7 days by serial dilution method2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.
AID45479In vitro antifungal activity against Candida albicans B311.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.
AID1493829Antifungal activity against Candida glabrata 537 after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID360003Cytotoxicity against human KB cells after 2 to 7 days by neutral red assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID1276315Inhibition of hypoxia-induced HIF-1 in human T47D cells cotransfected with pHRE-luciferase plasmid at 10 to 30 uM preincubated for 30 mins followed by hypoxia induction measured after 16 hrs by luciferase reporter gene assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID1276317Cytotoxicity against human T47D cells at 1 to 30 uM after 48 hrs by sulforhodamine B assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID774608Antimicrobial activity against Mycobacterium intracellulare2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and antimycobacterial activity of analogues of the bioactive natural products sampangine and cleistopholine.
AID1493831Antifungal activity against Aspergillus fumigatus 07544 after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID360015Inhibition of LFA1/ICAM1-mediated CFSE-labeled TPA-stimulated human HL60 cell adhesion to ICAM1 expressing human HeLa cells after 45 mins by fluorescence analysis2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
AID39700In vitro antifungal activity against Aspergillus fumigatus ATCC 26934.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.
AID1276327Increase in oxygen consumption rate of mitochondrial state 4 respiration in human T47D cells assessed as reinitiation of oligomycin-stalled cellular respiration by Clark-type oxygen electrode assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID1493832Antifungal activity against Trichophyton rubrum Cmccftla after 24 hrs by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.
AID1276322Cytostatic activity against human MDA-MB-231 cells at 1 to 30 uM after 48 hrs by sulforhodamine B assay in presence of ascorbate2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.
AID380337Antifungal activity against Candida albicans NIH B311 after 24 hrs by twofold serial dilution method2000Journal of natural products, May, Volume: 63, Issue:5
Characterization of the major metabolite of sampangine in rats.
AID360005Cytotoxicity against human SKOV3 cells after 2 to 7 days by neutral red assay2001Journal of natural products, May, Volume: 64, Issue:5
Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (8.00)18.2507
2000's7 (28.00)29.6817
2010's13 (52.00)24.3611
2020's3 (12.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.69

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

MetricThis Compound (vs All)
Research Demand Index11.69 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.69)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.1510sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
pyridine
azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.		2.0410azaarene;
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
pyridines		environmental contaminant;
NMR chemical shift reference compound
uroporphyrinogen iii
Uroporphyrinogens: Porphyrinogens which are intermediates in heme biosynthesis. They have four acetic acid and four propionic acid side chains attached to the pyrrole rings. Uroporphyrinogen I and III are formed from polypyrryl methane in the presence of uroporphyrinogen III cosynthetase and uroporphyrin I synthetase, respectively. They can yield uroporphyrins by autooxidation or coproporphyrinogens by decarboxylation.		2.0610uroporphyrinogenEscherichia coli metabolite;
mouse metabolite
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		210aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
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.		2.1110aromatic 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.		2.5320conazole 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.		210nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
hydroxyurea
[no description available]		2.1510one-carbon compound;
ureas		antimetabolite;
antimitotic;
antineoplastic agent;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
genotoxin;
immunomodulator;
radical scavenger;
teratogenic agent
ibuprofen
Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine		2.3110monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
environmental contaminant;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
radical scavenger;
xenobiotic
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.0810carbohydrazideantitubercular agent;
drug allergen
itraconazole
[no description available]		2.1710piperazines
quinone
benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).		7.11101,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
acetylene
[no description available]		2.0510alkyne;
gas molecular entity;
terminal acetylenic compound
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.1510cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		2.2110isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
boldine
[no description available]		3.3110aporphine alkaloid
streptomycin
[no description available]		2.0810antibiotic antifungal drug;
antibiotic fungicide;
streptomycins		antibacterial drug;
antifungal agrochemical;
antimicrobial agent;
antimicrobial drug;
bacterial metabolite;
protein synthesis inhibitor
eupolauridine
eupolauridine: azafluoranthene from Cleistopholis patens; structure given in first source; RN from Chem Abst. Index Guide 1986		2.0610naphthyridine derivativemetabolite
ascididemin
ascididemin: can be viewed as a fused phenanthroline with quinoline; from the Mediterranean ascidian Cystodytes dellechiajei; structure in first source		2.0810
cleistopholine
cleistopholine: structure in first source		2.7130
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		2.3920antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
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.		210cytochalasin;
lactam;
lactone;
organic heterotricyclic compound		actin polymerisation inhibitor;
metabolite;
mycotoxin;
platelet aggregation inhibitor
6-nonadecynoic acid
6-nonadecynoic acid: from the roots of Pentagonia gigantifolia; structure in first source		2.1510
heme
Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.		2.4620
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).		2.0110
iminoquinone
iminoquinone: an electrophile; structure in first source		2.1110
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.730cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
AIDS-Related Opportunistic Infections
Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.		01.9810
C gattii Infection
[description not available]		0210
Cryptococcosis
Fungal infection caused by genus CRYPTOCOCCUS.		0210
Cancer of Lung
[description not available]		02.0610
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0610
Benign Neoplasms
[description not available]		03.1210
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.		03.1210
Acute Confusional Senile Dementia
[description not available]		02.6920
Protein Aggregation, Pathological
A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.		02.2510
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.6920
Innate Inflammatory Response
[description not available]		02.3110
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.		02.3110
Candida Infection
[description not available]		02.1510
Candidiasis
Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)		02.1510