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
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Formula C34H67NO3
Net Charge 0
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]
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