Page last updated: 2024-12-07

hapalosin

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Description

hapalosin: cyclodepsipeptide; RN given refers to (2S-(2R*,5R*,6S*,10S*,11R*))-isomer; reverses multidrug resistance; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID133055
CHEMBL ID269137
MeSH IDM0288387

Synonyms (6)

Synonym
1,9-dioxa-4-azacyclododecane-3,8,12-trione, 10-heptyl-6-hydroxy-4,11-dimethyl-2-(1-methylethyl)-5-(phenylmethyl)-, (2s-(2r*,5r*,6s*,10s*,11r*))-
159542-04-8
hapalosin
CHEMBL269137
(2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-4,11-dimethyl-2-propan-2-yl-1,9-dioxa-4-azacyclododecane-3,8,12-trione
bdbm50403688
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATP-dependent translocase ABCB1Homo sapiens (human)IC50 (µMol)9.80000.00022.318510.0000AID154132; AID154133
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
G2/M transition of mitotic cell cycleATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic metabolic processATP-dependent translocase ABCB1Homo sapiens (human)
response to xenobiotic stimulusATP-dependent translocase ABCB1Homo sapiens (human)
phospholipid translocationATP-dependent translocase ABCB1Homo sapiens (human)
terpenoid transportATP-dependent translocase ABCB1Homo sapiens (human)
regulation of response to osmotic stressATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
transepithelial transportATP-dependent translocase ABCB1Homo sapiens (human)
stem cell proliferationATP-dependent translocase ABCB1Homo sapiens (human)
ceramide translocationATP-dependent translocase ABCB1Homo sapiens (human)
export across plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
positive regulation of anion channel activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
regulation of chloride transportATP-dependent translocase ABCB1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
protein bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingATP-dependent translocase ABCB1Homo sapiens (human)
ABC-type xenobiotic transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
efflux transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP hydrolysis activityATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ubiquitin protein ligase bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylcholine floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylethanolamine flippase activityATP-dependent translocase ABCB1Homo sapiens (human)
ceramide floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
cytoplasmATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
cell surfaceATP-dependent translocase ABCB1Homo sapiens (human)
membraneATP-dependent translocase ABCB1Homo sapiens (human)
apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
extracellular exosomeATP-dependent translocase ABCB1Homo sapiens (human)
external side of apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID9983MDR-reversing activity was measured by vincristine accumulation in the multidrug resistant 2780AD, a subline of A2780 ovarian carcinoma cells at 10 mg/mL2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
Synthesis and biological activities of hapalosin derivatives with modification at the C12 position.
AID82676Inhibitory concentration against HL-60/ADR cells using MRP-mediated MDR assay using 2 nM vincristine which inhibits cell proliferation by 20% in the absence of particular cytotoxic drug1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Design, synthesis, and evaluation of the multidrug resistance-reversing activity of D-glucose mimetics of hapalosin.
AID154133Multidrug-resistant reversal activity using P388/VMDRC.04 cells (a subline of P388 murine leukemia cells expressing human recombinant human P-glycoprotein) in the presence of 10 nM vincristine1999Bioorganic & medicinal chemistry letters, Jun-07, Volume: 9, Issue:11
Synthesis and evaluation of hapalosin and analogs as MDR-reversing agents.
AID103928Inhibitory concentration against MCF-7/ADR cells using P-gp-mediated MDR assay using 25 nM actinomycin D which inhibits cell proliferation by 20% in the absence of particular cytotoxic drug1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Design, synthesis, and evaluation of the multidrug resistance-reversing activity of D-glucose mimetics of hapalosin.
AID85445Compound was tested for the induction of apoptosis in human fibrosarcoma HT1080 cell line; No induction of apoptosis up to 10 ug/mL2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
Synthesis and biological activities of hapalosin derivatives with modification at the C12 position.
AID103923Effective concentration against MCF-7/ADR cells using P-gp-mediated MDR assay using 25 nM actinomycin D which results in 50% of the cells being killed in the presence of particular cytotoxic drug.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Design, synthesis, and evaluation of the multidrug resistance-reversing activity of D-glucose mimetics of hapalosin.
AID229315Ratio of IC50 of cytotoxicity to the IC50 of MDR- reversal for P388/VMDRC.04 cells1999Bioorganic & medicinal chemistry letters, Jun-07, Volume: 9, Issue:11
Synthesis and evaluation of hapalosin and analogs as MDR-reversing agents.
AID82675Effective concentration against HL-60/ADR cells using MRP-mediated MDR assay using 2 nM vincristine which results in 50% of the cells being killed in the presence of particular cytotoxic drug.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Design, synthesis, and evaluation of the multidrug resistance-reversing activity of D-glucose mimetics of hapalosin.
AID154132Evaluated for cytotoxicity using P388/VMDRC.04 cells (a subline of P388 murine leukemia cells expressing human recombinant human P-glycoprotein) in the absence of 10 nM vincristine1999Bioorganic & medicinal chemistry letters, Jun-07, Volume: 9, Issue:11
Synthesis and evaluation of hapalosin and analogs as MDR-reversing agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (37.50)18.2507
2000's3 (37.50)29.6817
2010's2 (25.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.65

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 Index19.65 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]