Page last updated: 2024-11-07

1-naphthylacetylspermine

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Cross-References

ID SourceID
PubMed CID129695
CHEMBL ID25101
CHEBI ID34097
SCHEMBL ID3403955
SCHEMBL ID22032651
MeSH IDM0185003

Synonyms (33)

Synonym
1-naphthylacetylspermine
122306-11-0
chebi:34097 ,
CHEMBL25101 ,
bdbm50100320
n-(3-(4-(3-aminopropylamino)butylamino)propyl)-2-(naphthalen-1-yl)acetamide
2-naphthalen-1-yl-1-(4-{[4-(2-piperidin-1-yl-ethylamino)-butylamino]-methyl}-piperidin-1-yl)-ethanone
n-{3-[4-(3-amino-propylamino)-butylamino]-propyl}-2-naphthalen-1-yl-acetamide
SCHEMBL3403955
n-[3-[4-(3-aminopropylamino)butylamino]propyl]-2-naphthalen-1-ylacetamide
ACMC-1BYBT ,
1-naphthylacetyl spermine
1-naphthaleneacetamide, n-(3-((4-((3-aminopropyl)amino)butyl)amino)propyl)-
1-na-spm
CS-3629
naspm
HY-12506
n-[3-[4-(3-aminopropylamino)butylamino]propyl]-2-(1-naphthyl)acetamide
DTXSID80153568
AKOS028111021
J-004786
GYY ,
n-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]-2-(naphthalen-1-yl)acetamide
naspm;1-na-spm;1-naphthyl acetyl spermine;1-naphthylacetyl spermine
BCP23925
Q27115805
A909519
n-(3-((4-((3-aminopropyl)amino)butyl)amino)propyl)-2-(naphthalen-1-yl)acetamide trihydrochloride
A906736
F85099
MS-25964
SCHEMBL22032651
1-naphthaleneacetamide, n-[3-[[4-[(3-aminopropyl)amino]butyl]amino]propyl]-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
[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 (18)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 12Homo sapiens (human)Ki0.19000.00021.10439.9000AID496922
Carbonic anhydrase 1Homo sapiens (human)Ki12.30000.00001.372610.0000AID496913
Carbonic anhydrase 2Homo sapiens (human)Ki1.13000.00000.72369.9200AID496914
Carbonic anhydrase 3Homo sapiens (human)Ki11.60000.00022.010210.0000AID496915
Glutamate receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)0.69000.00011.617910.0000AID92207; AID92208
Glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)0.69000.00011.700010.0000AID92207; AID92208
Glutamate receptor 3Rattus norvegicus (Norway rat)IC50 (µMol)0.69000.00011.700010.0000AID92207; AID92208
Glutamate receptor 4Rattus norvegicus (Norway rat)IC50 (µMol)0.69000.00011.700010.0000AID92207; AID92208
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki10.20000.00020.566510.0000AID496923
Carbonic anhydrase 4Homo sapiens (human)Ki0.01800.00021.97209.9200AID496916
Carbonic anhydrase 6Homo sapiens (human)Ki0.11000.00011.47109.9200AID496919
Carbonic anhydrase 5A, mitochondrialHomo sapiens (human)Ki1.03000.00001.27259.9000AID496917
Carbonic anhydrase 7Homo sapiens (human)Ki0.10000.00021.37379.9000AID496920
Carbonic anhydrase 9Homo sapiens (human)Ki0.12000.00010.78749.9000AID496921
Carbonic anhydrase 15Mus musculus (house mouse)Ki0.78000.00091.884610.0000AID496925
Carbonic anhydrase 13Mus musculus (house mouse)Ki10.20000.00021.39749.9000AID496923
Carbonic anhydrase 14Homo sapiens (human)Ki1.03000.00021.50999.9000AID496924
Carbonic anhydrase 5B, mitochondrialHomo sapiens (human)Ki1.05000.00001.34129.9700AID496918
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
estrous cycleCarbonic anhydrase 12Homo sapiens (human)
chloride ion homeostasisCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
response to bacteriumCarbonic anhydrase 3Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 3Homo sapiens (human)
bicarbonate transportCarbonic anhydrase 4Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 4Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of bitter tasteCarbonic anhydrase 6Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 6Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 7Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 7Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 7Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 7Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 7Homo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 14Homo sapiens (human)
response to bacteriumCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 12Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 12Homo sapiens (human)
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 3Homo sapiens (human)
protein bindingCarbonic anhydrase 3Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 3Homo sapiens (human)
nickel cation bindingCarbonic anhydrase 3Homo sapiens (human)
protein bindingCarbonic anhydrase 4Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 4Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 4Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 6Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 6Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 14Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 14Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (25)

Processvia Protein(s)Taxonomy
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
membraneCarbonic anhydrase 12Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 12Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 12Homo sapiens (human)
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 3Homo sapiens (human)
cytosolCarbonic anhydrase 3Homo sapiens (human)
cytoplasmCarbonic anhydrase 3Homo sapiens (human)
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
basolateral plasma membraneCarbonic anhydrase 4Homo sapiens (human)
rough endoplasmic reticulumCarbonic anhydrase 4Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentCarbonic anhydrase 4Homo sapiens (human)
Golgi apparatusCarbonic anhydrase 4Homo sapiens (human)
trans-Golgi networkCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
external side of plasma membraneCarbonic anhydrase 4Homo sapiens (human)
cell surfaceCarbonic anhydrase 4Homo sapiens (human)
membraneCarbonic anhydrase 4Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 4Homo sapiens (human)
transport vesicle membraneCarbonic anhydrase 4Homo sapiens (human)
secretory granule membraneCarbonic anhydrase 4Homo sapiens (human)
brush border membraneCarbonic anhydrase 4Homo sapiens (human)
perinuclear region of cytoplasmCarbonic anhydrase 4Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
extracellular regionCarbonic anhydrase 6Homo sapiens (human)
extracellular spaceCarbonic anhydrase 6Homo sapiens (human)
cytosolCarbonic anhydrase 6Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 6Homo sapiens (human)
extracellular spaceCarbonic anhydrase 6Homo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
cytosolCarbonic anhydrase 7Homo sapiens (human)
cytoplasmCarbonic anhydrase 7Homo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 14Homo sapiens (human)
membraneCarbonic anhydrase 14Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 14Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 14Homo sapiens (human)
plasma membraneCarbonic anhydrase 14Homo sapiens (human)
mitochondrionCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID496915Inhibition of human carbonic anhydrase 3 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496925Inhibition of mouse carbonic anhydrase 15 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496919Inhibition of human carbonic anhydrase 6 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID26786Dissociation constant2001Bioorganic & medicinal chemistry letters, Oct-08, Volume: 11, Issue:19
Synthesis of diaminobutane derivatives as potent Ca(2+)-permeable AMPA receptor antagonists.
AID496923Inhibition of mouse carbonic anhydrase 13 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496917Inhibition of human carbonic anhydrase 5A by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496920Inhibition of human carbonic anhydrase 7 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496914Inhibition of human carbonic anhydrase 2 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID101790Inhibition of [3H]spermidine transport into MDA-MB-231 (human breast cancer) cells.2001Journal of medicinal chemistry, Oct-25, Volume: 44, Issue:22
Amino acid/spermine conjugates: polyamine amides as potent spermidine uptake inhibitors.
AID496921Inhibition of human carbonic anhydrase 9 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496922Inhibition of human carbonic anhydrase 12 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496913Inhibition of human carbonic anhydrase 1 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496916Inhibition of human carbonic anhydrase 4 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID496924Inhibition of human carbonic anhydrase 14 by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID194905Change in systolic blood pressure(SBP) after intravenous administration of 3 mg/kg in rats compared with SBP before dosing2001Bioorganic & medicinal chemistry letters, May-21, Volume: 11, Issue:10
Synthesis of polyamine derivatives having non-hypotensive Ca2 +-permeable AMPA receptor antagonist activity.
AID174745Change in systolic blood pressure before and after intravenous administration of 3 mg/kg dose in rats2001Bioorganic & medicinal chemistry letters, Oct-08, Volume: 11, Issue:19
Synthesis of diaminobutane derivatives as potent Ca(2+)-permeable AMPA receptor antagonists.
AID92207Antagonist activity for [Ca2+] permeable Ionotropic glutamate receptor AMPA expressed in Xenopus oocytes by injection of rat brain mRNA2001Bioorganic & medicinal chemistry letters, May-21, Volume: 11, Issue:10
Synthesis of polyamine derivatives having non-hypotensive Ca2 +-permeable AMPA receptor antagonist activity.
AID496918Inhibition of human carbonic anhydrase 5B by stopped flow CO2 hydration method2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
AID92208Antagonistic activity against Ca++permeable Ionotropic glutamate receptor AMPA as concentration of compound that reduces the inward current induced by kainate by 50% in Xenopus oocytes2001Bioorganic & medicinal chemistry letters, Oct-08, Volume: 11, Issue:19
Synthesis of diaminobutane derivatives as potent Ca(2+)-permeable AMPA receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (50)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (12.00)18.2507
2000's18 (36.00)29.6817
2010's20 (40.00)24.3611
2020's6 (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: 10.95

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 Index10.95 (24.57)
Research Supply Index3.95 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.95)

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%
Other51 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]