Page last updated: 2024-12-11

dihydroceramide

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

Description

dihydroceramide: lacks the 4-5 trans double bond of the sphingosine moiety of ceramides; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N-acylsphinganine : A ceramide consisting of sphinganine in which one of the amino hydrogens is substituted by a fatty acyl group. [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]

dihydroceramide : An N-acylsphingoid obtained by formal condensation of the carboxy group of any fatty acid with the amino group of any dihydrosphingoid base. [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]

N-acetylsphinganine : A dihydroceramide in which the ceramide acyl group is specified as acetyl. [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 CID16755624
MeSH IDM0283793
PubMed CID6610273
CHEMBL ID155886
CHEBI ID64913
SCHEMBL ID1479036
MeSH IDM0283793

Synonyms (63)

Synonym
n-acylsphinganine
dihydroceramide
Q63153308
n-[(2s,3r)-1,3-dihydroxyoctadecan-2-yl]formamide
CBIOL_002032
BIO1_000807
BIO1_000318
BIO2_000767
BIO1_001296
BIO2_000287
IDI1_034037
BSPBIO_001567
dihydroceramide c2, >=98% (tlc), solid
NCGC00161358-01
NCGC00161358-02
c2 dihydroceramide
KBIO3_000573
KBIOGR_000287
KBIO3_000574
KBIO2_000287
KBIO2_005423
KBIO2_002855
KBIOSS_000287
NCGC00161358-03
c2-dihydroceramide
n-acetylsphinganine
HMS1989O09
13031-64-6
BML3-C11
HMS1361O09
HMS1791O09
chebi:64913 ,
CHEMBL155886
n-[(2s,3r)-1,3-dihydroxyoctadecan-2-yl]acetamide
SCHEMBL1479036
n-acetyldihydrosphingosine
dihydro-c2-ceramide
tic-016
n-acetyl dihydrosphingosine
d-erythro-1,3-dihydroxy-2-acetamidooctadecane
zzk8x1cr0r ,
d-erythro-2-acetamido-1,3-octadecanediol
unii-zzk8x1cr0r
acetamide, n-((1s,2r)-2-hydroxy-1-(hydroxymethyl)heptadecyl)-
ds-n-acetylsphinganine
acetamide, n-(2-hydroxy-1-(hydroxymethyl)heptadecyl)-, (r-(r*,s*))-
n-acetyl dihydrosphingosine [inci]
acetamide, n-(2-hydroxy-1-(hydroxymethyl)heptadecyl)-, d-erythro-
d-erythro-n-acetylsphinganine
BRD-K62910157-001-01-9
CCG-208049
CRJGESKKUOMBCT-VQTJNVASSA-N
(2s,3r)-2-acetylaminooctadecane-1,3-diol
HMS3402O09
DTXSID20156452
J-005790
c2 dihydroceramide (d18:0/2:0), n-acetoyl-d-erythro-sphinganine, powder
26561-61-5
acetamide, n-[(1r,2s)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-, rel-
Q27133532
c2-dihydro-ceramide (n-acetyl-)
acetamide,n-[(1r,2s)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-,rel-
BP-28805

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" Sphingolipid (SL) analogues can promote tumour response in combination with anticancer drugs."( Increased tumour dihydroceramide production after Photofrin-PDT alone and improved tumour response after the combination with the ceramide analogue LCL29. Evidence from mouse squamous cell carcinomas.
Bielawski, J; Korbelik, M; Merchant, S; Ogretmen, B; Pierce, JS; Separovic, D; Tarca, AL, 2009
)
0.35
" In the present work, TMZ was combined with a specific SKI, and the cytotoxic effect of each drug alone or in combination was tested on GBM cell lines."( A sphingosine kinase inhibitor combined with temozolomide induces glioblastoma cell death through accumulation of dihydrosphingosine and dihydroceramide, endoplasmic reticulum stress and autophagy.
Choi, J; Kopp-Schneider, A; Noack, J; Régnier-Vigouroux, A; Richter, K, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylsphinganineA ceramide consisting of sphinganine in which one of the amino hydrogens is substituted by a fatty acyl group.
[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]

Pathways (14)

PathwayProteinsCompounds
Sphingolipid Metabolism2335
Gaucher Disease2335
Globoid Cell Leukodystrophy2335
Metachromatic Leukodystrophy (MLD)2335
Fabry Disease2335
Krabbe Disease2335
Synthesis of ceramides and 1-deoxyceramides115
sphingolipid recycling and degradation (yeast)820
sphingolipid biosynthesis (mammals)914
ceramide de novo biosynthesis712
sphingolipid biosynthesis (plants)1226
ceramide biosynthesis1010
Sphingolipid pathway315
Metabolism of sphingolipids in ER and Golgi apparatus144

Bioassays (18)

Assay IDTitleYearJournalArticle
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.
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.
AID521220Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID421663Antibacterial activity against Shigella sonnei ATCC 11060 at 100 ug/disk2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID1627826Cytostatic activity against mouse FL5.12A cells after 48 hrs by DAPI staining-based flow cytometric analysis2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Effects of stereochemistry, saturation, and hydrocarbon chain length on the ability of synthetic constrained azacyclic sphingolipids to trigger nutrient transporter down-regulation, vacuolation, and cell death.
AID421659Antibacterial activity against Enterobacter aerogenes ATCC 13048 at 100 ug/disk2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID81276Apoptotic activity against HL-60 (Human leukemia) cell after 6 hr of stimulation measured by MTT assay2003Bioorganic & medicinal chemistry letters, Feb-24, Volume: 13, Issue:4
Synthesis of non-natural C2-homo-ceramide and its apoptotic activity against HL-60 cells.
AID421660Antibacterial activity against Serratia marcescens ATCC 25419 at 100 ug/disk2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID421665Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced COX2 protein level at 10 uM by immunoblot analysis relative to control2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID1627823Induction of vacuolation in mouse FL5.12A cells assessed as vacuolation score at 50 uM measured at 3 hrs by fluorescence microscopic analysis2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Effects of stereochemistry, saturation, and hydrocarbon chain length on the ability of synthetic constrained azacyclic sphingolipids to trigger nutrient transporter down-regulation, vacuolation, and cell death.
AID393057Cytotoxicity against human SupT1 cells after 24 hrs by CellTiter-Blue assay2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency.
AID421664Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced iNOS protein level at 10 uM by immunoblot analysis relative to control2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID421666Effect on beta-actin protein expression in LPS-stimulated mouse RAW264.7 cells at 10 uM by immunoblot analysis relative to control2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID421662Antibacterial activity against Yersinia enterocolitica ATCC 23715 at 100 ug/disk2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID421661Antibacterial activity against Salmonella enteritidis ATCC 13076 at 100 ug/disk2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.
AID1627824Downregulation of CD8 expression level in mouse FL5.12A cells at 50 uM measured at 3 hrs by flow cytometric analysis2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Effects of stereochemistry, saturation, and hydrocarbon chain length on the ability of synthetic constrained azacyclic sphingolipids to trigger nutrient transporter down-regulation, vacuolation, and cell death.
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.
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 (166)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (5.42)18.2507
2000's56 (33.73)29.6817
2010's66 (39.76)24.3611
2020's35 (21.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.76

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.76 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index41.22 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.26%)5.53%
Trials0 (0.00%)5.53%
Reviews12 (7.55%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational1 (0.63%)0.25%
Observational0 (0.00%)0.25%
Other144 (90.57%)84.16%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]