Page last updated: 2024-12-08

4-amino-2-deoxy-2,3-didehydro-n-acetylneuraminic acid

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Cross-References

ID SourceID
PubMed CID445533
CHEMBL ID52270
SCHEMBL ID8565789
MeSH IDM0217186

Synonyms (28)

Synonym
(2r,3r,4s)-3-acetamido-4-amino-2-[(1r,2r)-1,2,3-trihydroxypropyl]-3,4-dihydro-2h-pyran-6-carboxylic acid
(4s,5r,6r)-5-acetylamino-4-amino-6-((1r,2r)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4h-pyran-2-carboxylic acid
4-amino-neu5ac2en
4-amino-2-deoxy-2,3-dehydro-n-acetyl-neuraminic acid
1F8C
4-amino-4-deoxy-neu5ac2en
des(carbamimidoyl) zanamivir
2QWD
4-am-dana
DB03321
4AM ,
4-amino-2-deoxy-2,3-dehydro-n-neuraminic acid
CHEMBL52270 ,
(4s,5r,6r)-5-acetamido-4-amino-6-((1r,2r)-1,2,3-trihydroxypropyl)-5,6-dihydro-4h-pyran-2-carboxylic acid
(2r,3r,4s)-3-acetamido-4-amino-2-((1r,2r)-1,2,3-trihydroxypropyl)-3,4-dihydro-2h-pyran-6-carboxylic acid
bdbm50063303
130525-62-1
unii-oe4l5bbv9m
d-glycero-d-galacto-non-2-enonic acid, 5-(acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-
4-amino-2-deoxy-2,3-didehydro-n-acetylneuraminic acid
oe4l5bbv9m ,
zanamivir amine
5-(acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-d-glycero-d-galacto-non-2-enonic acid
NKENBBIXEGPQLS-UFGQHTETSA-N
SCHEMBL8565789
F16186
zanamivir hydrate impurity c [ep impurity]
(2r,3r,4s)-3-(acetylamino)-4-amino-2-((1r,2r)-1,2,3-trihydroxypropyl)-3,4-dihydro-2h-pyran-6-carboxylic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (17)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, NeuraminidaseInfluenza A virus (A/tern/Australia/G70C/1975(H11N9))Ki0.04000.04002.02004.0000AID977610
Chain A, NeuraminidaseInfluenza A virus (A/tern/Australia/G70C/1975(H11N9))Ki0.04000.04002.02004.0000AID977610
Chain A, NeuraminidaseInfluenza A virus (A/tern/Australia/G70C/1975(H11N9))Ki0.04000.04002.02004.0000AID977610
Chain A, NeuraminidaseInfluenza A virus (A/tern/Australia/G70C/1975(H11N9))Ki0.04000.04002.02004.0000AID977610
Chain A, NeuraminidaseInfluenza A virusKi14.00000.033098.0110280.0000AID977610
Chain A, NeuraminidaseInfluenza A virusKi14.00000.033098.0110280.0000AID977610
Chain A, NeuraminidaseInfluenza A virusKi14.00000.033098.0110280.0000AID977610
Chain A, NEURAMINIDASEInfluenza A virusKi14.00000.033098.0110280.0000AID977610
Chain A, NeuraminidaseInfluenza A virusKi14.00000.033098.0110280.0000AID977610
Neuraminidase Influenza A virus (A/Wilson-Smith/1933(H1N1))IC50 (µMol)159,981.66000.00000.503510.0000AID384920; AID636870
Neuraminidase Influenza A virus (A/Wilson-Smith/1933(H1N1))Ki0.04000.00011.78687.7000AID488379
NeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))IC50 (µMol)0.32000.00050.976710.0000AID203531
NeuraminidaseInfluenza B virus (B/Lee/1940)IC50 (µMol)0.41000.00100.402810.0000AID203529
Sialidase-4Homo sapiens (human)IC50 (µMol)720.00008.30008.30008.3000AID729054
Sialidase-3Homo sapiens (human)IC50 (µMol)180.00002.40005.99808.1700AID729055
Sialidase-2Homo sapiens (human)IC50 (µMol)44.00003.90006.73337.8000AID729057
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
viral release from host cellNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
glycoprotein catabolic processSialidase-4Homo sapiens (human)
ganglioside catabolic processSialidase-4Homo sapiens (human)
oligosaccharide catabolic processSialidase-4Homo sapiens (human)
negative regulation of neuron projection developmentSialidase-4Homo sapiens (human)
oligosaccharide catabolic processSialidase-1Homo sapiens (human)
ganglioside catabolic processSialidase-1Homo sapiens (human)
carbohydrate metabolic processSialidase-3Homo sapiens (human)
ganglioside catabolic processSialidase-3Homo sapiens (human)
oligosaccharide catabolic processSialidase-3Homo sapiens (human)
positive regulation of epidermal growth factor receptor signaling pathwaySialidase-3Homo sapiens (human)
glycosphingolipid catabolic processSialidase-3Homo sapiens (human)
negative regulation of clathrin-dependent endocytosisSialidase-3Homo sapiens (human)
glycoprotein catabolic processSialidase-2Homo sapiens (human)
ganglioside catabolic processSialidase-2Homo sapiens (human)
oligosaccharide catabolic processSialidase-2Homo sapiens (human)
glycosphingolipid catabolic processSialidase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
exo-alpha-sialidase activityNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
peptidase activator activityNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
exo-alpha-sialidase activitySialidase-4Homo sapiens (human)
protein bindingSialidase-4Homo sapiens (human)
exo-alpha-(2->3)-sialidase activitySialidase-4Homo sapiens (human)
exo-alpha-(2->6)-sialidase activitySialidase-4Homo sapiens (human)
exo-alpha-(2->8)-sialidase activitySialidase-4Homo sapiens (human)
exo-alpha-sialidase activitySialidase-1Homo sapiens (human)
protein bindingSialidase-1Homo sapiens (human)
alpha-sialidase activitySialidase-1Homo sapiens (human)
exo-alpha-(2->3)-sialidase activitySialidase-1Homo sapiens (human)
exo-alpha-(2->6)-sialidase activitySialidase-1Homo sapiens (human)
exo-alpha-(2->8)-sialidase activitySialidase-1Homo sapiens (human)
exo-alpha-sialidase activitySialidase-3Homo sapiens (human)
protein bindingSialidase-3Homo sapiens (human)
alpha-sialidase activitySialidase-3Homo sapiens (human)
exo-alpha-(2->3)-sialidase activitySialidase-3Homo sapiens (human)
exo-alpha-(2->6)-sialidase activitySialidase-3Homo sapiens (human)
exo-alpha-(2->8)-sialidase activitySialidase-3Homo sapiens (human)
exo-alpha-sialidase activitySialidase-2Homo sapiens (human)
protein bindingSialidase-2Homo sapiens (human)
exo-alpha-(2->3)-sialidase activitySialidase-2Homo sapiens (human)
exo-alpha-(2->6)-sialidase activitySialidase-2Homo sapiens (human)
exo-alpha-(2->8)-sialidase activitySialidase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (22)

Processvia Protein(s)Taxonomy
extracellular regionNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
plasma membraneNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
lysosomeSialidase-4Homo sapiens (human)
mitochondrial outer membraneSialidase-4Homo sapiens (human)
mitochondrial inner membraneSialidase-4Homo sapiens (human)
lysosomeSialidase-4Homo sapiens (human)
endoplasmic reticulum membraneSialidase-4Homo sapiens (human)
plasma membraneSialidase-4Homo sapiens (human)
organelle inner membraneSialidase-4Homo sapiens (human)
neuron projectionSialidase-4Homo sapiens (human)
lysosomal lumenSialidase-4Homo sapiens (human)
lysosomeSialidase-4Homo sapiens (human)
cytoplasmSialidase-4Homo sapiens (human)
membraneSialidase-4Homo sapiens (human)
extracellular regionSialidase-1Homo sapiens (human)
lysosomeSialidase-1Homo sapiens (human)
lysosomal membraneSialidase-1Homo sapiens (human)
plasma membraneSialidase-1Homo sapiens (human)
cell junctionSialidase-1Homo sapiens (human)
specific granule lumenSialidase-1Homo sapiens (human)
lysosomal lumenSialidase-1Homo sapiens (human)
intracellular membrane-bounded organelleSialidase-1Homo sapiens (human)
extracellular exosomeSialidase-1Homo sapiens (human)
lysosomeSialidase-1Homo sapiens (human)
cytoplasmSialidase-1Homo sapiens (human)
membraneSialidase-1Homo sapiens (human)
lysosomal membraneSialidase-3Homo sapiens (human)
plasma membraneSialidase-3Homo sapiens (human)
caveolaSialidase-3Homo sapiens (human)
external side of plasma membraneSialidase-3Homo sapiens (human)
early endosome membraneSialidase-3Homo sapiens (human)
recycling endosome membraneSialidase-3Homo sapiens (human)
membraneSialidase-3Homo sapiens (human)
lysosomeSialidase-3Homo sapiens (human)
cytoplasmSialidase-3Homo sapiens (human)
cytosolSialidase-2Homo sapiens (human)
catalytic complexSialidase-2Homo sapiens (human)
lysosomeSialidase-2Homo sapiens (human)
membraneSialidase-2Homo sapiens (human)
cytoplasmSialidase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID147491In vitro inhibitory activity against neuraminidase2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 2. Computational titration and pH effects in molecular models of neuraminidase-inhibitor complexes.
AID488379Inhibition of Influenza A virus neuraminidase2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses.
AID384920Inhibition of influenza virus neuraminidase2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
QSAR study of neuraminidase inhibitors based on heuristic method and radial basis function network.
AID203527Compound was tested for the inhibition of influenza virus sialidase using 2'-(4-methylumbelliferyl)-N-acetylneuraminic acid substrate1996Journal of medicinal chemistry, Jan-19, Volume: 39, Issue:2
A study of the active site of influenza virus sialidase: an approach to the rational design of novel anti-influenza drugs.
AID729049Selectivity ratio of IC50 for human neuraminidase 1 to IC50 for human neuraminidase 22013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID729055Inhibition of human neuraminidase 3 expressed in Escherichia coli using 4MU-NANA as substrate after 30 mins by fluorescence assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID488378Antiviral activity against Influenza A virus (A/Singapore/1/1957 (H2N2)) infected in MDCK cells assessed as inhibition of virus-induced plaque formation2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses.
AID728984Selectivity ratio of IC50 for human neuraminidase 3 to IC50 for human neuraminidase 22013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID729057Inhibition of human neuraminidase 2 expressed in Escherichia coli using 4MU-NANA as substrate after 30 mins by fluorescence assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID704188Inhibition of Influenza A virus sialidase N2 by fluorometric assay2012Journal of medicinal chemistry, Oct-25, Volume: 55, Issue:20
Exploring the interactions of unsaturated glucuronides with influenza virus sialidase.
AID729048Selectivity ratio of IC50 for human neuraminidase 4 to IC50 for human neuraminidase 22013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID729056Inhibition of human neuraminidase 1 using 4MU-NANA as substrate after 30 mins by fluorescence assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID203529Compound was tested for inhibitory concentration against Influenza sialidase type B1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B.
AID203531Compound was tested for inhibitory concentration against Influenza sialidase type A1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B.
AID729058Inhibition of Vibrio cholerae neuraminidase2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID636870Inhibition of influenza A virus neuraminidase2011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The de-guanidinylated derivative of peramivir remains a potent inhibitor of influenza neuraminidase.
AID729054Inhibition of human neuraminidase 4 using 4MU-NANA as substrate after 30 mins by fluorescence assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2001Protein science : a publication of the Protein Society, Apr, Volume: 10, Issue:4
Analysis of inhibitor binding in influenza virus neuraminidase.
AID1811Experimentally measured binding affinity data derived from PDB2001Protein science : a publication of the Protein Society, Apr, Volume: 10, Issue:4
Analysis of inhibitor binding in influenza virus neuraminidase.
AID1811Experimentally measured binding affinity data derived from PDB1998Structure (London, England : 1993), Jun-15, Volume: 6, Issue:6
Drug design against a shifting target: a structural basis for resistance to inhibitors in a variant of influenza virus neuraminidase.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1998Structure (London, England : 1993), Jun-15, Volume: 6, Issue:6
Drug design against a shifting target: a structural basis for resistance to inhibitors in a variant of influenza virus neuraminidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (42.86)18.2507
2000's4 (28.57)29.6817
2010's4 (28.57)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: 11.66

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 Index11.66 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.66)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]