N-hexadecanoylsphingosine (CHEBI:72959)

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CHEBI:72959 - N-hexadecanoylsphingosine

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ChEBI Name	N-hexadecanoylsphingosine

ChEBI ID	CHEBI:72959

ChEBI ASCII Name	N-hexadecanoylsphingosine

Definition	A N-acylsphingosine in which the ceramide N-acyl group is specified as hexadecanoyl (palmitoyl).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Alan Bridge

Secondary ChEBI IDs	CHEBI:39603

Supplier Information	eMolecules:715863, ZINC000008860497

Download	Molfile XML SDF

more structures >>

Molfile

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M END): 38 ms

reading 105 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

105 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Formula

C34H67NO3

Net Charge

Average Mass

537.914

Monoisotopic Mass

537.51210

InChI

InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1

InChIKey

YDNKGFDKKRUKPY-TURZORIXSA-N

SMILES

CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC

Metabolite of Species	Details
Mycoplasma genitalium (NCBI:txid2097)	See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed

Roles Classification
Biological Role(s):	Mycoplasma genitalium metabolite Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium. human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via N-acylsphingosine )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	N-hexadecanoylsphingosine (CHEBI:72959) has functional parent hexadecanoic acid (CHEBI:15756) N-hexadecanoylsphingosine (CHEBI:72959) has role Mycoplasma genitalium metabolite (CHEBI:131604) N-hexadecanoylsphingosine (CHEBI:72959) has role human blood serum metabolite (CHEBI:85234) N-hexadecanoylsphingosine (CHEBI:72959) is a N-acylsphingosine (CHEBI:52639) N-hexadecanoylsphingosine (CHEBI:72959) is a N-palmitoyl-sphingoid base (CHEBI:144703) N-hexadecanoylsphingosine (CHEBI:72959) is a Cer(d34:1) (CHEBI:137569)

IUPAC Name

N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide

Synonyms	Sources
(2S,3R,4E)-2-acylamino-1,3-octadec-4-enediol	HMDB
(2S,3R,4E)-2-acylaminooctadec-4-ene-1,3-diol	HMDB
C16 Cer	LIPID MAPS
C16 Ceramide	ChEBI
C16-0(Palmitoyl)ceramide	ChemIDplus
Cer(d18:1/16:0)	LIPID MAPS
Ceramide (d18:1/16:0)	HMDB
N-(hexadecanoyl)-sphing-4-enine	ChEBI
N-(hexadecanoyl)ceramide	LIPID MAPS
N-(hexadecanoyl)sphing-4-enine	SUBMITTER
N-(palmitoyl)ceramide	LIPID MAPS
N-hexadecanoyl-D-erythro-sphingosine	ChEBI
N-hexadecanoylsphing-4-enine	SUBMITTER
N-hexadecanoylsphing-4-enine	UniProt
N-palmitoyl-sphingosine	ChEBI
N-palmitoylsphing-4-enine	ChEBI
N-palmitoylsphingosine	ChEBI

Manual Xrefs	Databases
16C	PDBeChem
FDB023536	FooDB
HMDB0004949	HMDB
LMSP02010004	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
1717423	Reaxys Registry Number	Reaxys
4201-58-5	CAS Registry Number	ChemIDplus

Citations

Jyonouchi S, Abraham V, Orange JS, Spergel JM, Gober L, Dudek E, Saltzman R, Nichols KE, Cianferoni A (2011)
Invariant natural killer T cells from children with versus without food allergy exhibit differential responsiveness to milk-derived sphingomyelin.
The Journal of allergy and clinical immunology 128, 102-109.e13 [PubMed:21458849]
[show Abstract]

Kudo N, Kumagai K, Tomishige N, Yamaji T, Wakatsuki S, Nishijima M, Hanada K, Kato R (2008)
Structural basis for specific lipid recognition by CERT responsible for nonvesicular trafficking of ceramide.
Proceedings of the National Academy of Sciences of the United States of America 105, 488-493 [PubMed:18184806]
[show Abstract]

Panjarian S, Kozhaya L, Arayssi S, Yehia M, Bielawski J, Bielawska A, Usta J, Hannun YA, Obeid LM, Dbaibo GS (2008)
De novo N-palmitoylsphingosine synthesis is the major biochemical mechanism of ceramide accumulation following p53 up-regulation.
Prostaglandins & other lipid mediators 86, 41-48 [PubMed:18400537]
[show Abstract]

Megha, Sawatzki P, Kolter T, Bittman R, London E (2007)
Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts).
Biochimica et biophysica acta 1768, 2205-2212 [PubMed:17574203]
[show Abstract]

Sot J, Goñi FM, Alonso A (2005)
Molecular associations and surface-active properties of short- and long-N-acyl chain ceramides.
Biochimica et biophysica acta 1711, 12-19 [PubMed:15904658]
[show Abstract]

Duclos RI (2001)
The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog.
Chemistry and physics of lipids 111, 111-138 [PubMed:11457441]
[show Abstract]

Di Paola M, Cocco T, Lorusso M (2000)
Ceramide interaction with the respiratory chain of heart mitochondria.
Biochemistry 39, 6660-6668 [PubMed:10828984]
[show Abstract]
A study is presented on the interaction of ceramide with the respiratory chain of rat heart mitochondria, and a comparison is made between the effects elicited by short- and long-chain ceramides. N-Acetylsphingosine (C(2)-ceramide) and N-palmitoylsphingosine (C(16)-ceramide) inhibited to the same extent the pyruvate+malate-dependent oxygen consumption. Succinate-supported respiration was also inhibited by ceramides, but this activity was substantially restored upon the addition of cytochrome c, which, on the contrary, was ineffective toward the ceramide-inhibited NADH-linked substrate oxidation. Direct measurements showed that short- and long-chain ceramides caused a large release of cytochrome c from mitochondria. The ceramide-dependent inhibition of pyruvate+malate and succinate oxidation caused reactive oxygen species to be produced at the level of either complex I or complex III. The activity of the cytochrome c oxidase, measured as ascorbate/TMPD oxidase activity, was significantly stimulated and inhibited by C(2)- and C(16)-ceramide, respectively. Similar effects were observed on the activity of the individual respiratory complexes isolated from bovine heart. Short- and long-chain ceramides had definitely different effects on the mitochondrial membrane potential. C(2)-ceramide caused an almost complete collapse of the respiration-dependent membrane potential, whereas C(16)-ceramide had a negligible effect. Similar results were obtained when the potential was generated in liposome-reconstituted complex III respiring at the steady-state. Furthermore, C(2)-ceramide caused a drop of the membrane potential generated by ATP hydrolysis instead of respiration, whereas C(16)-ceramide did not. Finally, only short-chain ceramides inhibited markedly the reactive oxygen species generation associated with membrane potential-dependent reverse electron flow from succinate to complex I. The emerging indication is that the short-chain ceramide-dependent collapse of membrane potential is a consequence of their ability to perturb the membrane structure, leading to an unspecific increase of its permeability.

Jin JS, Tsai CS, Si X, Webb RC (1999)
Endothelium dependent and independent relaxations induced by ceramide in vascular smooth muscles.
The Chinese journal of physiology 42, 47-51 [PubMed:10405771]
[show Abstract]

Okino N, Tani M, Imayama S, Ito M (1998)
Purification and characterization of a novel ceramidase from Pseudomonas aeruginosa.
The Journal of biological chemistry 273, 14368-14373 [PubMed:9603946]
[show Abstract]

Gomes NA, Previato JO, Zingales B, Mendonça-Previato L, DosReis GA (1996)
Down-regulation of T lymphocyte activation in vitro and in vivo induced by glycoinositolphospholipids from Trypanosoma cruzi. Assignment of the T cell-suppressive determinant to the ceramide domain.
Journal of immunology (Baltimore, Md. : 1950) 156, 628-635 [PubMed:8543814]
[show Abstract]

Last Modified

13 October 2020

ChEBI

CHEBI:72959 - N-hexadecanoylsphingosine

Background

Objective

Methods

Results

Conclusion

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