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Information on EC 2.3.1.24 - sphingosine N-acyltransferase and Organism(s) Homo sapiens and UniProt Accession Q6ZMG9

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EC Tree
IUBMB Comments
Acts on sphingosine or its 2-epimer.
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This record set is specific for:
Homo sapiens
UNIPROT: Q6ZMG9
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
Synonyms
ceramide synthase, cers6, cers5, cers4, lass5, ceramide synthase 6, lass6, ceramide synthase 5, sphinganine n-acyltransferase, (dihydro)ceramide synthase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C16:0-CerS
-
longevity assurance homolog 6
-
longevity assurance homologue 6
-
acyltransferase, sphingosine
-
-
-
-
C16:0-CerS
-
ceramide synthase
-
-
ceramide synthase 4
-
ceramide synthetase
-
-
-
-
longevity assurance homologue 5
-
sphinganine N-acyl transferase synthase
-
-
sphingosine acyltransferase
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -
SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:sphingosine N-acyltransferase
Acts on sphingosine or its 2-epimer.
CAS REGISTRY NUMBER
COMMENTARY hide
37257-09-3
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dihydrosphingosine + myristoyl-CoA
N-myristoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoylsphinganine + CoA
show the reaction diagram
sphingosine + 2-hydroxy-palmitoyl-CoA
N-2-hydroxy-palmitoyl-sphingosine + CoA
show the reaction diagram
-
-
-
?
sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
show the reaction diagram
dihydrosphingosine + myristoyl-CoA
N-myristoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
show the reaction diagram
best substrate
-
-
?
dihydrosphingosine + stearoyl-CoA
N-stearoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
docosanoyl-CoA + sphingosine
CoA + N-docosanoylsphingosine
show the reaction diagram
-
-
-
?
eicosanoyl-CoA + sphingosine
CoA + N-eicosanoylsphingosine
show the reaction diagram
-
-
-
?
hexacosanoyl-CoA + sphingosine
CoA + N-hexacosanoylsphingosine
show the reaction diagram
-
-
-
?
palmitoyl-CoA + sphingosine
CoA + N-palmitoylsphingosine
show the reaction diagram
palmitoyl-CoA + sphingosine
CoA + palmitoylsphingosine
show the reaction diagram
sphinganine + arachidoyl-CoA
N-arachidoylsphinganine + CoA
show the reaction diagram
-
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoyl-DL-dihydrosphingosine + CoA
show the reaction diagram
-
-
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoylsphinganine + CoA
show the reaction diagram
sphinganine + stearoyl-CoA
N-stearoylsphinganine + CoA
show the reaction diagram
-
-
-
?
sphingosine + 2-hydroxy-palmitoyl-CoA
N-2-hydroxy-palmitoyl-sphingosine + CoA
show the reaction diagram
-
-
-
?
sphingosine + eicosanoyl-CoA
N-eicosanoylsphingosine + CoA
show the reaction diagram
-
-
-
?
sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
show the reaction diagram
stearoyl-CoA + sphingosine
CoA + N-stearoylsphingosine
show the reaction diagram
-
-
-
?
tetracosanoyl-CoA + sphingosine
CoA + N-tetracosanoylsphingosine
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dihydrosphingosine + myristoyl-CoA
N-myristoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoylsphinganine + CoA
show the reaction diagram
sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
show the reaction diagram
dihydrosphingosine + myristoyl-CoA
N-myristoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
show the reaction diagram
best substrate
-
-
?
dihydrosphingosine + stearoyl-CoA
N-stearoyldihydrosphingosine + CoA
show the reaction diagram
-
-
-
?
sphinganine + arachidoyl-CoA
N-arachidoylsphinganine + CoA
show the reaction diagram
-
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoyl-DL-dihydrosphingosine + CoA
show the reaction diagram
-
-
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoylsphinganine + CoA
show the reaction diagram
sphinganine + stearoyl-CoA
N-stearoylsphinganine + CoA
show the reaction diagram
-
-
-
?
sphingosine + eicosanoyl-CoA
N-eicosanoylsphingosine + CoA
show the reaction diagram
-
-
-
?
sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
fumonisin B1
FTY720
fumonisin B1
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
daunorubicin
-
an anthracycline used in the treatment of leukemia, increases the enzyme activity and ceramide production, and inhibits the apoptosis of leukmeia cells
N-(4-hydroxyphenyl)retinamide
-
i.e. 4-HPR or fenretinide, elevates ceramide in neuroblastoma cell lines by coordinating activation of serine palmitoyltransferase and ceramide synthase. 4-HPR treatment does not accelerate cellular decay of sphingomyelin
additional information
-
vincristine (100 nM), methotrexate (200 nM), etoposide (0.003 mM), and cis-platinum (0.05 mM) do not stimulate ceramide synthase
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
isozymes CerS2 (EC 2.3.1.297) and CerS6 (EC 2.3.1.24) mRNA is significantly elevated in breast cancer tissue compared to normal tissue, with approximately half of the individuals showing elevated CerS2 and CerS6 mRNA. A significant correlation is found between CerS2 and CerS6 isozyme expression, and between isozymes CerS4 (EC 2.3.1.24) and CerS2/CerS6 expression
Manually annotated by BRENDA team
human hepatoma HepG2 cells stably transfected with recombinant plasmids carrying the murine alcohol dehydrogenase gene and the human cytochrome P450 2E1 gene, in vitro model of alcoholic steatosis
Manually annotated by BRENDA team
high expression level of CerS6
Manually annotated by BRENDA team
epidermal, expression analysis of the CerS family members during keratinocyte differentiation, overview
Manually annotated by BRENDA team
CerS2 and CerS6 are the major very long-chain and long-chain CerS isoforms in MCF-7 cells, respectively
Manually annotated by BRENDA team
isozymes CerS2 (EC 2.3.1.297) and CerS6 (EC 2.3.1.24) mRNA is significantly elevated in breast cancer tissue compared to normal tissue, with approximately half of the individuals showing elevated CerS2 and CerS6 mRNA. A significant correlation is found between CerS2 and CerS6 isozyme expression, and between isozymes CerS4 (EC 2.3.1.24) and CerS2/CerS6 expression
Manually annotated by BRENDA team
epidermal, expression analysis of the CerS family members during keratinocyte differentiation, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
recombinant FLAG-tagged CerS6 localizes primarily to the perinuclear region
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
malfunction
metabolism
physiological function
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
CERS6_HUMAN
384
5
44890
Swiss-Prot
Secretory Pathway (Reliability: 1)
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
CerS activity can be modulated by dimer formation. CerS5 activity is inhibited in a dominant-negative fashion by co-expression with catalytically inactive CerS5. CerS dimers are formed rapidly upon stimulation of ceramide synthesis
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H220A/H221A
site-directed mutagenesis, mutation of the two residues involved in catalytic activity completely abrogates CerS5 activity in a constitutive dimer
additional information
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
subcellular fractionation of HeLa cells recombinantly expressing the CerS isozyme
subcellular fractionation of HeLa cells recombinantly expressing the CerS isozyme
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene CERS6, isozyme expression analysis
gene CERS6, quantitative real-time PCR enzyme expression analysis
gene CERS6, recombinant expression in HEK-293T cells, quantitative real-time quantitative PCR enzyme expression analysis
gene CERS6, recombinant expression of N-terminally FLAG-tagged CerS6 and EGFP-tagged CerS6 in SW-480 cells and localization in the perinuclear region. When cells transfected with pCerS6-IRES2-EGFP are treated with TRAIL, GFP positive cells appear to be undergoing apoptosis. Cells stably transfected with CerS6 but not with the empty plasmid acquire a TRAIL sensitive phenotype
gene CERS6, recombinant FLAG-tagged isozyme overexpression in HeLa cells, quantitative real-time PCR enzyme expression analysis, CerS6 overexpression yields no significant differences in IR-induced apoptosis compared to empty vector-transfected cells. CerS2, CerS5, and CerS6 form heterocomplexes in transformed HeLa cells
expression in HEK-293T cell
gene CERS4, isozyme expression analysis
gene CERS4, recombinant overexpression in HEK cells
gene CERS5, quantitative real-time PCR enzyme expression analysis
gene CERS5, recombinant expression in HEK-293T cells, quantitative real-time quantitative PCR enzyme expression analysis
gene CERS5, recombinant expression of HA-tagged wild-type enzyme, and point mutants as well as truncated CerS5DELTAC332-392 mutant and chimeric mutant enzyme in HEK-293 cells, recombinant expression of FLAG-tagged CerS5 in HEK-293 cells
gene CERS5, recombinant FLAG-tagged isozyme overexpression in HeLa cells, quantitative real-time PCR enzyme expression analysis, CerS5 overexpression significantly increases apoptosis in a time- and dose-dependent manner compared to empty vector-transfected controls. CerS2, CerS5, and CerS6 form heterocomplexes in transformed HeLa cells
gene CERS5, recombinant overexpression in HEK cells, FTY720 inhibits CerS1 activity to a greater extent than CerS5 in the overexpressing cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CerS6 is upregulated in alcoholic steatosis and in response to ethanol
ionizing radiation (IR) induces de novo synthesis of ceramide by specifically activating CerS isoforms 2, 5, and 6
ionizing radiation (IR) induces de novo synthesis of ceramide by specifically activating CerS isoforms 2, 5, and 6
UV-C irradiation decreases the expression of CerS5 enzyme by about 50%
RENATURED/Commentary
ORGANISM
UNIPROT
LITERATURE
recombinant HA-tagged wild-type CerS5 and HA-tagged chimeric mutant CerS5:TM:CerS2 are reconstituted in 1,2-dioleoyl-sn-glycero-3-phosphocholine liposomes
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
diagnostics
important role for the CerS genes in breast cancer etiology or diagnosis, overview
medicine
isoform CerS6 is specifically upregulated in experimental alcoholic steatosis in vivo and in vitro
analysis
-
fluorescent CERS assay with quantification using thin-layer chromatography or high-performance liquid chromatography
diagnostics
important role for the CerS genes in breast cancer etiology or diagnosis, overview
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Erez-Roman, R.; Pienik, R.; Futerman, A.H.
Increased ceramide synthase 2 and 6 mRNA levels in breast cancer tissues and correlation with sphingosine kinase expression
Biochem. Biophys. Res. Commun.
391
219-223
2010
Homo sapiens (Q6ZMG9), Homo sapiens (Q9HA82), Homo sapiens
Manually annotated by BRENDA team
Wang, H.; Maurer, B.J.; Reynolds, C.P.; Cabot, M.C.
N-(4-Hydroxyphenyl)retinamide elevates ceramide in neuroblastoma cell lines by coordinate activation of serine palmitoyltransferase and ceramide synthase
Cancer Res.
61
5102-5105
2001
Homo sapiens
Manually annotated by BRENDA team
Bose, R.; Verheji, M.; Haimovitz-Friedman, A.; Scotto, K.; Fuks, Z.; Kolesnick, R.
Ceramide synthase mediates daunorubicin-induced apoptosis an alternative mechanism for generating death signals
Cell
82
405-414
1995
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Mesicek, J.; Lee, H.; Feldman, T.; Jiang, X.; Skobeleva, A.; Berdyshev, E.V.; Haimovitz-Friedman, A.; Fuks, Z.; Kolesnick, R.
Ceramide synthases 2, 5, and 6 confer distinct roles in radiation-induced apoptosis in HeLa cells
Cell. Signal.
22
1300-1307
2010
Homo sapiens (Q6ZMG9), Homo sapiens (Q8N5B7)
Manually annotated by BRENDA team
Lahiri, S.; Park, H.; Laviad, E.L.; Lu, X.; Bittman, R.; Futerman, A.H.
Ceramide synthesis is modulated by the sphingosine analog FTY720 via a mixture of uncompetitive and noncompetitive inhibition in an Acyl-CoA chain length-dependent manner
J. Biol. Chem.
284
16090-16098
2009
Homo sapiens (Q8N5B7), Homo sapiens (Q9HA82)
Manually annotated by BRENDA team
Mullen, T.D.; Jenkins, R.W.; Clarke, C.J.; Bielawski, J.; Hannun, Y.A.; Obeid, L.M.
Ceramide synthase-dependent ceramide generation and programmed cell death involvement of salvage pathway in regulating postmitochondrial events
J. Biol. Chem.
286
15929-15942
2011
Homo sapiens (Q6ZMG9), Homo sapiens (Q8N5B7)
Manually annotated by BRENDA team
Laviad, E.L.; Kelly, S.; Merrill, A.H.; Futerman, A.H.
Modulation of ceramide synthase activity via dimerization
J. Biol. Chem.
287
21025-21033
2012
Homo sapiens (Q8N5B7)
Manually annotated by BRENDA team
Sassa, T.; Hirayama, T.; Kihara, A.
Enzyme activities of the ceramide synthases CERS2-6 are regulated by phosphorylation in the C-terminal region
J. Biol. Chem.
291
7477-7487
2016
Homo sapiens (Q8IU89), Homo sapiens (Q8N5B7), Homo sapiens (Q96G23), Homo sapiens (Q9HA82), Homo sapiens (Q9NTG7), Mus musculus (Q924Z4), Mus musculus
Manually annotated by BRENDA team
Mizutani, Y.; Kihara, A.; Chiba, H.; Tojo, H.; Igarashi, Y.
2-Hydroxy-ceramide synthesis by ceramide synthase family enzymatic basis for the preference of FA chain length
J. Lipid Res.
49
2356-2364
2008
Homo sapiens (Q6ZMG9), Homo sapiens (Q8N5B7)
Manually annotated by BRENDA team
Lim, X.Y.; Pickford, R.; Don, A.S.
Assaying ceramide synthase activity in vitro and in living cells using liquid chromatography-mass spectrometry
Methods Mol. Biol.
1376
11-22
2016
Homo sapiens (Q6ZMG9), Homo sapiens (Q8N5B7), Homo sapiens (Q9HA82)
Manually annotated by BRENDA team
White-Gilbertson, S.; Mullen, T.; Senkal, C.; Lu, P.; Ogretmen, B.; Obeid, L.; Voelkel-Johnson, C.
Ceramide synthase 6 modulates TRAIL sensitivity and nuclear translocation of active caspase-3 in colon cancer cells
Oncogene
28
1132-1141
2009
Homo sapiens (Q6ZMG9)
Manually annotated by BRENDA team
Williams, B.; Correnti, J.; Oranu, A.; Lin, A.; Scott, V.; Annoh, M.; Beck, J.; Furth, E.; Mitchell, V.; Senkal, C.E.; Obeid, L.; Carr, R.M.
A novel role for ceramide synthase 6 in mouse and human alcoholic steatosis
FASEB J.
32
130-142
2018
Homo sapiens (Q6ZMG9), Homo sapiens, Mus musculus (Q8C172), Mus musculus
Manually annotated by BRENDA team
Tidhar, R.; Zelnik, I.; Volpert, G.; Ben-Dor, S.; Kelly, S.; Merrill, A.; Futerman, A.
Eleven residues determine the acyl chain specificity of ceramide synthases
J. Biol. Chem.
293
9912-9921
2018
Homo sapiens (Q8N5B7), Homo sapiens (Q9HA82)
Manually annotated by BRENDA team
Couttas, T.; Don, A.
Fluorescent assays for ceramide synthase activity
Methods Mol. Biol.
1376
23-33
2016
Homo sapiens
Manually annotated by BRENDA team