Page last updated: 2024-12-10

fees

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

Description

1-O-(alpha-D-galactopyranosyl)-N-tetracosanyl-2-aminononane-1,3,4-triol : A glycophytoceramide comprising (2S,3S,4R)-2-aminononane-1,3,4-triol having an alpha-D-galctopyranosyl residue at the O-1 position and an tetracosanoyl group attached to the nitrogen. [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]

Cross-References

ID SourceID
PubMed CID2826714
CHEMBL ID231993
CHEBI ID495150
SCHEMBL ID552249
MeSH IDM0008291

Synonyms (26)

Synonym
FEE ,
n-{(1s,2s,3r)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyoctyl}tetracosanamide
n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonan-2-yl]tetracosanamide
tetracosanamide, n-[(1s,2s,3r)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyoctyl]- (9ci)
tetracosanamide, n-[(1s,2s,3r)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyoctyl]-
383187-82-4
och ,
CHEMBL231993
n-[(2s,3s,4r)-1-(alpha-d-galactopyranosyloxy)-3,4-dihydroxynonan-2-yl]tetracosanamide
och9
och (pbs 20)
1-o-(alpha-d-galactopyranosyl)-n-tetracosanyl-2-aminononane-1,3,4-triol
galalpha-cer(t9:0/24:0)
chebi:495150 ,
(2s,3s,4r)-1-o-(alpha-d-galactopyranosyl)-n-tetracosanyl-2-aminononane-1,3,4-triol
EPITOPE ID:141799
SCHEMBL552249
3G08
3ARB
HB4004
c39h77no9
(2s,3s,4r)-1-o-(alpha-d-galactopyranosyl)-n-tetracosanoyl-2-amino-1,3,4-nonanetriol)
DTXSID00385102
LMFA13010062
Q27225755
PD018104
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
epitopeThe biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
[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 (1)

ClassDescription
glycophytoceramideA phytoceramide having at least one glycosyl group attached to either of its hydroxy groups.
[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 (11)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Antigen-presenting glycoprotein CD1d1Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain C, NKT Valpha14-Jalpha18,NKT Valpha14-Jalpha18Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain A, Antigen-presenting glycoprotein CD1d1Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain C, NKT Valpha14-Jalpha18,NKT Valpha14-Jalpha18Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain A, Antigen-presenting glycoprotein CD1d1Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain C, NKT Valpha14-Jalpha18,NKT Valpha14-Jalpha18Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain A, Antigen-presenting glycoprotein CD1d1Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain C, NKT Valpha14-Jalpha18,NKT Valpha14-Jalpha18Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain A, Antigen-presenting glycoprotein CD1d1Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain C, NKT Valpha14-Jalpha18,NKT Valpha14-Jalpha18Mus musculus (house mouse)Kd0.23400.23400.23400.2340AID977611
Chain A, T-cell surface glycoprotein CD1d1Mus musculus (house mouse)Kd0.00680.00680.00680.0068AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID677316Immunostimulatory activity in C57BL/6 mouse splenocytes assessed as IFN-gamma release at 100 ng/ml after 72 hrs by ELISA relative to OCH2012Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9
Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile.
AID425892Stimulation of human iNKT cell proliferation2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH.
AID295919Induction of IFN gamma secretion in C57BL/6 mouse spleen cells at 100 ng/ml after 72 hrs relative to OCH2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.
AID1593616Induction of serum IFNgamma production in C57BL/6 mouse at 100 ug/kg, ip and measured for 48 hrs by AUC method relative to KRN70002019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID387827Induction of IL13 production in C57BL/6 mouse natural killer T cells after 48 hrs by cytometric bead array2008Bioorganic & medicinal chemistry, Oct-01, Volume: 16, Issue:19
RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.
AID1593615Induction of serum IL-4 production in C57BL/6 mouse assessed as serum IL-4 level at 100 ug/kg, ip and measured for 48 hrs by AUC method2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID1593617Induction of serum IL-4 production in C57BL/6 mouse at 100 ug/kg, ip and measured for 48 hrs by AUC method relative to KRN70002019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID387826Induction of IL4 production in C57BL/6 mouse natural killer T cells after 48 hrs by cytometric bead array2008Bioorganic & medicinal chemistry, Oct-01, Volume: 16, Issue:19
RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.
AID1593619Induction of serum IL-4 production in C57BL/6 mouse assessed as serum IL-4 level at 100 ug/kg, ip and measured for 48 hrs by peak value method2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID1593614Induction of serum IFNgamma production in C57BL/6 mouse assessed as serum IFNgamma level at 100 ug/kg, ip and measured for 48 hrs by AUC method2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID1593623Ratio of induction activity for IL-4 production in C57BL/6 mouse at 100 ug/kg, ip after 48 hrs by peak value method to induction activity for IFN-gamma production in C57BL/6 mouse at 100 ug/kg, ip after 48 hrs by peak value method2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID677319Immunostimulatory activity iv dosed in C57BL/6 mouse assessed as IL-4 secretion2012Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9
Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile.
AID1593622Induction of serum IFNgamma production in C57BL/6 mouse assessed as serum IFNgamma level at 100 ug/kg, ip and measured for 48 hrs by peak value method relative to KRN70002019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID677315Immunostimulatory activity in C57BL/6 mouse splenocytes assessed as IL-4 release at 100 ng/ml after 72 hrs by ELISA relative to OCH2012Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9
Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile.
AID1593621Induction of serum IFNgamma production in C57BL/6 mouse assessed as serum IFNgamma level at 100 ug/kg, ip and measured for 48 hrs by peak value method2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID677322Immunostimulatory activity iv dosed in C57BL/6 mouse assessed as IFN-gamma secretion2012Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9
Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile.
AID575776Antibacterial activity against Sphingomonas capsulata ATCC 14666 infected in C57BL/6 mouse assessed as reduction in lung bacterial load at 100 ug/kg, ip administered 2 hrs post infection measured 24 hrs post infection2010Antimicrobial agents and chemotherapy, Oct, Volume: 54, Issue:10
In vivo protection provided by a synthetic new alpha-galactosyl ceramide analog against bacterial and viral infections in murine models.
AID1593620Induction of serum IL-4 production in C57BL/6 mouse assessed as serum IL-4 level at 100 ug/kg, ip and measured for 48 hrs by peak value method relative to KRN70002019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID425889Stimulation of mouse splenocyte proliferation by [3H]thymidine after 48 hrs by incorporation assay2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH.
AID295918Induction of IL4 secretion in C57BL/6 mouse spleen cells at 100 ng/ml after 72 hrs relative to OCH2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.
AID1509403Binding affinity to CD1d in C57BL/6 mouse HMNC cells assessed as iNKT cells stimulation by measuring Th1-type cytokine, IFNgamma production at 25 nM incubated for 72 hrs by ELISA2019ACS medicinal chemistry letters, May-09, Volume: 10, Issue:5
Development of α-GalCer Analogues with an α-Fluorocarbonyl Moiety as Th2-Selective Ligands of CD1d.
AID1593618Ratio of induction activity for IL-4 production in C57BL/6 mouse at 100 ug/kg, ip after 48 hrs by AUC method to induction activity for IFN-gamma production in C57BL/6 mouse at 100 ug/kg, ip after 48 hrs by AUC method2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Design, synthesis, and evaluation of α-galactopyranosylceramide mimics promoting Th2 cytokines production.
AID1509402Binding affinity to CD1d in C57BL/6 mouse HMNC cells assessed as iNKT cells stimulation by measuring increase in Th2-type cytokine, IL-4 production at 25 nM incubated for 72 hrs by ELISA2019ACS medicinal chemistry letters, May-09, Volume: 10, Issue:5
Development of α-GalCer Analogues with an α-Fluorocarbonyl Moiety as Th2-Selective Ligands of CD1d.
AID1509410Binding affinity to CD1d in C57BL/6 mouse HMNC cells assessed as iNKT cells stimulation by measuring increase in ratio of IL-4 to IFNgamma (IL-4/IFNgamma) level at 25 nM incubated for 72 hrs by ELISA2019ACS medicinal chemistry letters, May-09, Volume: 10, Issue:5
Development of α-GalCer Analogues with an α-Fluorocarbonyl Moiety as Th2-Selective Ligands of CD1d.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2011Immunity, Mar-25, Volume: 34, Issue:3
A molecular basis for the exquisite CD1d-restricted antigen specificity and functional responses of natural killer T cells.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2010Journal of immunology (Baltimore, Md. : 1950), Jan-01, Volume: 184, Issue:1
Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's6 (66.67)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: 116.63

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index116.63 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index207.66 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (116.63)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]