Page last updated: 2024-08-01 21:11:36

2,3-n-octanoylsphingosine

Description

N-octanoylsphingosine : An N-acylsphingosine in which the ceramide N-acyl group is specified as octanoyl. [CHeBI]

Cross-References

ID SourceID
PubMed CID5702614
CHEMBL ID444463
SCHEMBL ID14020687
CHEBI ID45815
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

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.

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency89.1251AID1490
glucocerebrosidaseHomo sapiens (human)Potency25.1189AID2101

Bioassays (30)

Assay IDTitleYearJournalArticle
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
ISSN: 1872-9096
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
ISSN: 1091-6490
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
ISSN: 2211-1247
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
ISSN: 1520-4804
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
ISSN: 0163-3864
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
ISSN: 1520-4804
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
ISSN: 1098-6596
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
ISSN: 1464-3405
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
ISSN: 1464-3391
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
ISSN: 1520-4804
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
ISSN: 1464-3405
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
ISSN: 1464-3405
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
ISSN: 1520-4804
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
ISSN: 1520-4804
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
ISSN: 1464-3391
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
ISSN: 1520-4804
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
ISSN: 1098-6596
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
ISSN: 1464-3391
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
ISSN: 1520-4804
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
ISSN: 1520-4804
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
ISSN: 1464-3391
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
ISSN: 1464-3405
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
ISSN: 1520-4804
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
ISSN: 1520-4804
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
ISSN: 1520-4804
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
ISSN: 1464-3405
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
ISSN: 1464-3405
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
ISSN: 1520-4804
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
ISSN: 1098-6596
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
ISSN: 1464-3405
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

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

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%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
n-palmitoylsphingosineCer(d34:1);
N-acylsphingosine;
N-palmitoyl-sphingoid base
human blood serum metabolite;
Mycoplasma genitalium metabolite
00low000000
n-acetylsphingosineN-acylsphingosine00low000000
n-caproylsphingosineN-acylsphingosine00low000000
n-(7-(4-nitrobenzo-2-oxa-1,3-diazole))-6-aminocaproyl sphingosineN-acylsphingosinefluorescent probe00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
tacrineacridines;
aromatic amine
EC 3.1.1.7 (acetylcholinesterase) inhibitor2010201014.0low000100
amiodarone1-benzofurans;
aromatic ketone;
organoiodine compound;
tertiary amino compound
cardiovascular drug2010201014.0low000100
amitriptylinecarbotricyclic compound;
tertiary amine
adrenergic uptake inhibitor;
antidepressant;
environmental contaminant;
tropomyosin-related kinase B receptor agonist;
xenobiotic
2010201014.0low000100
azelastinemonochlorobenzenes;
phthalazines;
tertiary amino compound
anti-allergic agent;
anti-asthmatic drug;
bronchodilator agent;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
H1-receptor antagonist;
platelet aggregation inhibitor
2010201014.0low000100
carvedilolcarbazoles;
secondary alcohol;
secondary amino compound
alpha-adrenergic antagonist;
antihypertensive agent;
beta-adrenergic antagonist;
cardiovascular drug;
vasodilator agent
2010201014.0low000100
clomipraminedibenzoazepineanticoronaviral agent;
antidepressant;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
serotonergic antagonist;
serotonergic drug;
serotonin uptake inhibitor
2010201014.0low000100
doxazosinaromatic amine;
benzodioxine;
monocarboxylic acid amide;
N-acylpiperazine;
N-arylpiperazine;
quinazolines
alpha-adrenergic antagonist;
antihyperplasia drug;
antihypertensive agent;
antineoplastic agent;
vasodilator agent
2010201014.0low000100
fluphenazineN-alkylpiperazine;
organofluorine compound;
phenothiazines
anticoronaviral agent;
dopaminergic antagonist;
phenothiazine antipsychotic drug
2010201014.0low000100
fluoxetine(trifluoromethyl)benzenes;
aromatic ether;
secondary amino compound
2010201014.0low000100
haloperidolaromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol
antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist
2010201014.0low000100
homochlorocyclizinediarylmethane2010201014.0low000100
lomerizinediarylmethane2010201014.0low000100
loperamidemonocarboxylic acid amide;
monochlorobenzenes;
piperidines;
tertiary alcohol
anticoronaviral agent;
antidiarrhoeal drug;
mu-opioid receptor agonist
2010201014.0low000100
loratadinebenzocycloheptapyridine;
ethyl ester;
N-acylpiperidine;
organochlorine compound;
tertiary carboxamide
anti-allergic agent;
cholinergic antagonist;
geroprotector;
H1-receptor antagonist
2010201014.0low000100
naftopidilpiperazines2010201014.0low000100
nefazodonearomatic ether;
monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
triazoles
alpha-adrenergic antagonist;
analgesic;
antidepressant;
serotonergic antagonist;
serotonin uptake inhibitor
2010201014.0low000100
perphenazineN-(2-hydroxyethyl)piperazine;
N-alkylpiperazine;
organochlorine compound;
phenothiazines
antiemetic;
dopaminergic antagonist;
phenothiazine antipsychotic drug
2010201014.0low000100
prazosinaromatic ether;
furans;
monocarboxylic acid amide;
piperazines;
quinazolines
alpha-adrenergic antagonist;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
2010201014.0low000100
promazinephenothiazines;
tertiary amine
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
muscarinic antagonist;
phenothiazine antipsychotic drug;
serotonergic antagonist
2010201014.0low000100
raloxifene1-benzothiophenes;
aromatic ketone;
N-oxyethylpiperidine;
phenols
bone density conservation agent;
estrogen antagonist;
estrogen receptor modulator
2010201014.0low000100
sibutramineorganochlorine compound;
tertiary amino compound
anti-obesity agent;
serotonin uptake inhibitor
2010201014.0low000100
imatinibaromatic amine;
benzamides;
N-methylpiperazine;
pyridines;
pyrimidines
antineoplastic agent;
apoptosis inducer;
tyrosine kinase inhibitor
2010201014.0low000100
norethindrone acetate3-oxo-Delta(4) steroid;
acetate ester;
terminal acetylenic compound
progestin;
synthetic oral contraceptive
2010201014.0low000100
cycloheximideantibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol
anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
2010201014.0low000100
phenothiazinephenothiazineferroptosis inhibitor;
plant metabolite;
radical scavenger
2010201014.0low000100
cyproterone acetate20-oxo steroid;
3-oxo-Delta(4) steroid;
acetate ester;
chlorinated steroid;
steroid ester
androgen antagonist;
geroprotector;
progestin
2010201014.0low000100
kainic aciddicarboxylic acid;
L-proline derivative;
non-proteinogenic L-alpha-amino acid;
pyrrolidinecarboxylic acid
antinematodal drug;
excitatory amino acid agonist
2010201014.0low000100
3,3',4',5-tetrachlorosalicylanilidedichlorobenzene;
salicylanilides
drug allergen2010201014.0low000100
metergolinecarbamate ester;
ergoline alkaloid
dopamine agonist;
geroprotector;
serotonergic antagonist
2010201014.0low000100
clobetasol propionate11beta-hydroxy steroid;
20-oxo steroid;
3-oxo-Delta(1),Delta(4)-steroid;
chlorinated steroid;
fluorinated steroid;
glucocorticoid
anti-inflammatory drug2010201014.0low000100
amitrazformamidines;
tertiary amino compound
acaricide;
environmental contaminant;
insecticide;
xenobiotic
2010201014.0low000100
bopindololaromatic ether;
benzoate ester;
methylindole;
secondary amino compound
2010201014.0low000100
nelfinaviraryl sulfide;
benzamides;
organic heterobicyclic compound;
phenols;
secondary alcohol;
tertiary amino compound
antineoplastic agent;
HIV protease inhibitor
2010201014.0low000100
dyclonine hydrochloridehydrochloridetopical anaesthetic2010201014.0low000100
ergocornineergot alkaloid2010201014.0low000100
1-benzylimidazole2010201014.0low000100
mephentermine2-aminooctadecane-1,3-diolEC 2.7.11.13 (protein kinase C) inhibitor;
human metabolite;
mouse metabolite
1998199826.0low001000
u 74006fcorticosteroid hormone2010201014.0low000100
desloratadinebenzocycloheptapyridineanti-allergic agent;
cholinergic antagonist;
drug metabolite;
H1-receptor antagonist
2010201014.0low000100
docetaxelhydrate;
secondary alpha-hydroxy ketone
antineoplastic agent2010201014.0low000100
terconazole1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine2010201014.0low000100
dihydroergocristine monomesylatemethanesulfonate saltalpha-adrenergic antagonist;
geroprotector;
vasodilator agent
2010201014.0low000100
sm 86682010201014.0low000100
posaconazolearomatic ether;
conazole antifungal drug;
N-arylpiperazine;
organofluorine compound;
oxolanes;
triazole antifungal drug;
triazoles
trypanocidal drug2010201014.0low000100
benztropinediarylmethane2010201014.0low000100
sphingosinesphing-4-eninehuman metabolite;
mouse metabolite
1998199826.0low001000
mycophenolate mofetilcarboxylic ester;
ether;
gamma-lactone;
phenols;
tertiary amino compound
anticoronaviral agent;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
immunosuppressive agent;
prodrug
2010201014.0low000100
n,n-dimethylsphingenineaminodiol;
sphingoid;
tertiary amino compound
EC 2.7.1.91 (sphingosine kinase) inhibitor;
metabolite
1998199826.0low001000
n-palmitoylsphingosineCer(d34:1);
N-acylsphingosine;
N-palmitoyl-sphingoid base
human blood serum metabolite;
Mycoplasma genitalium metabolite
1998199826.0low001000
vinorelbineacetate ester;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
ring assembly;
vinca alkaloid
antineoplastic agent;
photosensitizing agent
2010201014.0low000100
furazolidone2010201014.0low000100
nitrofurazone2010201014.0low000100
n-acetylsphingosineN-acylsphingosine1998199826.0low001000
n-caproylsphingosineN-acylsphingosine1998199826.0low001000
nifurtimoxnitrofuran antibiotic2010201014.0low000100
nifursol2010201014.0medium000100
naloxonazine2010201014.0low000100
rwj 683542010201014.0high000100
mk 9362010201014.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
American Trypanosomiasis02010201014.0low000100
Breast Cancer02009201213.7medium000210
Breast Neoplasms02009201213.7medium000210
Cancer of Colon02012201212.0low000010
Cancer of Lung02012201212.0low000010
Chagas Disease02010201014.0low000100
Colonic Neoplasms02012201212.0low000010
Congenital Zika Syndrome0202020204.0low000010
Disease Models, Animal0202020204.0low000010
Encephalitis, Polio02011201113.0low000010
Lung Neoplasms02012201212.0low000010
Poliomyelitis02011201113.0low000010
Zika Virus Infection0202020204.0low000010