Page last updated: 2024-12-11

2,3-n-octanoylsphingosine

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

Description

N-octanoylsphingosine : An N-acylsphingosine in which the ceramide N-acyl group is specified as octanoyl. [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 CID5702614
CHEMBL ID444463
CHEBI ID45815
SCHEMBL ID14020687
MeSH IDM0181508

Synonyms (42)

Synonym
IDI1_034039
BSPBIO_001569
NCGC00161360-01
NCGC00161360-02
c8 ceramide
NCGC00161360-03
HMS1989O11
n-octanoyl-d-erythro-sphingosine
74713-59-0
BML3-D01
HMS1361O11
HMS1791O11
n-[(e,2s,3r)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
chebi:45815 ,
n-octanoylsphingosine
CHEMBL444463
c8-ceramide
c-8 ceramide
n-[(2s,3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
n-octanoyl sphingosine
cer(d18:1/8:0)
n-octanoylsphing-4-enine
SCHEMBL14020687
APDLCSPGWPLYEQ-WRBRXSDHSA-N
HMS3649E13
HMS3402O11
n-octanoylsphingosine,d-erythro
c8 ceramide (d18:1/8:0), n-octanoyl-d-erythro-sphingosine, powder
n-((2s,3r,e)-1,3-dihydroxyoctadec-4-en-2-yl)octanamide
mfcd00236496
EX-A1429
Q27120632
sr-01000946565
SR-01000946565-1
ceramide 8; d-erythro-n-octanoylsphingosine; n-octanoyl-c18-sphingosine
AS-56387
AKOS037645042
n-[(1s,2r,3e)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-octanamide
HY-108391
DTXSID701318293
CS-0028558
BP-28810
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylsphingosineThe parent compounds of the ceramide family, composed of sphingosine having an unspecified fatty acyl group attached to the nitrogen.
[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 (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency89.12510.141337.9142100.0000AID1490
glucocerebrosidaseHomo sapiens (human)Potency25.11890.01268.156944.6684AID2101
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID431777Selectivity for tumor necrosis factor-resistant human MCF7 cells over human MCF10A cells2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID401377Toxicity against Ulva conglobata at 50 ppm1998Journal of natural products, Jun-26, Volume: 61, Issue:6
New ceramide from marine sponge Haliclona koremella and related compounds as antifouling substances against macroalgae.
AID431784Increase in endogenous sphingosine-1-phosphate level in tumor necrosis factor-resistant human MCF7 cells at 10 uM after by ESI/MS/MS analysis2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID547622Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM cells measured after 88 hrs postinfection by HTS assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.
AID654948Potentiation of etoposide-induced antiproliferative activity against human MCF-7TN-R cells after 24 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
Anti-proliferative effects of the novel ceramide analog (S)-2-(benzylideneamino)-3-hydroxy-N-tetrade-cylpropanamide in chemoresistant cancer.
AID658812Induction of apoptosis in human HCT116 cells at 30 uM after 14 hrs by Annexin V-propidium iodide staining based flow cytometry2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
3-Deoxy-3,4-dehydro analogs of XM462. Preparation and activity on sphingolipid metabolism and cell fate.
AID431775Antiproliferative activity against tumor necrosis factor-resistant human MCF7 cells after 24 hrs by MTT assay2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID654837Antiproliferative activity against human MDA-MB-231 cells assessed as decrease in Ki-67 staining after 48 hrs by immunofluorescence staining2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
Anti-proliferative effects of the novel ceramide analog (S)-2-(benzylideneamino)-3-hydroxy-N-tetrade-cylpropanamide in chemoresistant cancer.
AID654838Antiproliferative activity against human MDA-MB-468 cells assessed as decrease in Ki-67 staining after 48 hrs by immunofluorescence staining2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
Anti-proliferative effects of the novel ceramide analog (S)-2-(benzylideneamino)-3-hydroxy-N-tetrade-cylpropanamide in chemoresistant cancer.
AID431769Inhibition of clonogenic survival of endocrine-resistant human MDA-MB-231 cells after 10 days by microscopy2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID431776Antiproliferative activity against human MCF10A cells at 100 uM after 24 hrs by MTT assay2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID492066Cytotoxicity against human MCF-7TN-R cells assessed as reduction in cell viability after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Novel anti-viability ceramide analogs: design, synthesis, and structure-activity relationship studies of substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides.
AID431774Antiproliferative activity against endocrine-resistant human MDA-MB-231 cells after 24 hrs by MTT assay2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID547621Cytotoxicity against BESM cells after 88 hrs by HTS assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.
AID1069719Induction of apoptosis in human MCF-7TN-R cells at 2 times IC50 determined from MTT assay after 24 hrs by ELISA relative to control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
3-Ketone-4,6-diene ceramide analogs exclusively induce apoptosis in chemo-resistant cancer cells.
AID431768Inhibition of clonogenic survival of human MCF7 cells after 10 days by microscopy2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID431771Induction of apoptosis in human MCF7 cells assessed as appearance of nucleosomes in cytoplasm at 8.3 uM after 24 hrs by ELISA relative to DMSO control2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID1069717Induction of apoptosis in human MCF-7TN-R cells assessed as caspase-9 activation at 2 times IC50 determined from MTT assay after 24 hrs by caspase Glo 9 assay relative to vehicle-treated control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
3-Ketone-4,6-diene ceramide analogs exclusively induce apoptosis in chemo-resistant cancer cells.
AID654949Potentiation of doxorubicin-induced antiproliferative activity against human MCF-7TN-R cells after 24 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
Anti-proliferative effects of the novel ceramide analog (S)-2-(benzylideneamino)-3-hydroxy-N-tetrade-cylpropanamide in chemoresistant cancer.
AID431783Increase in endogenous sphingosine-1-phosphate level in endocrine-resistant human MDA-MB-231 cells at 10 uM after by ESI/MS/MS analysis2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID431782Increase in endogenous sphingosine-1-phosphate level in human MCF7 cells at 10 uM after by ESI/MS/MS analysis2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID431770Inhibition of clonogenic survival of tumor necrosis factor-resistant human MCF7 cells after 10 days by microscopy2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID654950Induction of apoptosis in human MCF-7TN-R cells assessed as decrease in viable cells after 48 hrs by DAPI staining method relative to control2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
Anti-proliferative effects of the novel ceramide analog (S)-2-(benzylideneamino)-3-hydroxy-N-tetrade-cylpropanamide in chemoresistant cancer.
AID654836Antiproliferative activity against human MCF-7TN-R cells assessed as decrease in Ki-67 staining after 48 hrs by immunofluorescence staining2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
Anti-proliferative effects of the novel ceramide analog (S)-2-(benzylideneamino)-3-hydroxy-N-tetrade-cylpropanamide in chemoresistant cancer.
AID431773Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay2009Journal of medicinal chemistry, Sep-24, Volume: 52, Issue:18
Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells.
AID547804Selectivity window, ratio of EC50 for BESM cells to EC50 for Trypanosoma cruzi amastigotes infected in BESM cells2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (9.09)18.2507
2000's1 (9.09)29.6817
2010's7 (63.64)24.3611
2020's2 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.52

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 Index12.52 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.52)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]