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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-03-24 16:16:40 UTC
Update Date2022-03-07 02:51:14 UTC
HMDB IDHMDB0011772
Secondary Accession Numbers
  • HMDB11772
Metabolite Identification
Common NameCer(d18:0/26:1(17Z))
DescriptionCer(d18:0/26:1(17Z)), also known as N-17Z-hexacosenoyl-sphinganine, is a ceramide (Cer). Ceramides are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). In humans, ceramides are phosphorylated to ceramide phosphates (CerPs) through the action of a specific ceramide kinase (CerK). Ceramide phosphates are important metabolites of ceramides as they act as a mediators of the inflammatory response. Ceramides are also one of the hydrolysis byproducts of sphingomyelins (SMs) through the action of the enzyme sphingomyelin phosphodiesterase, which has been identified in the subcellular fractions of human epidermis (PMID: 25935 ) and many other tissues. Ceramides can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID: 14998372 ). Ceramides are key in the biosynthesis of glycosphingolipids and gangliosides. In terms of its appearance and structure, Cer(d18:0/26:1(17Z)) is a colorless solid that consists of a saturated 18-carbon sphingoid base with an attached unsaturated 17Z-hexacosenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Data?1582752949
Synonyms
ValueSource
C26:1DH CerChEBI
N-(17Z-Hexacosenoyl)-dihydroceramideChEBI
N-[(17Z)-Hexacosenoyl]dihydrosphingosineChEBI
N-[(17Z)-Tetracosenoyl]dihydrosphingosineChEBI
N-C26:1-17Z-SphinganineChEBI
N-Hexacos-17cis-enoylsphinganineChEBI
N-XimenoyldihydrosphingosineChEBI
N-XimenoylsphinganineChEBI
CeramideHMDB
N-(17Z-Hexacosenoyl)-sphinganineHMDB
Ceramide(D18:0/26:1(17Z))HMDB
N-(17Z-Hexacosenoyl)-dihydrosphingosineHMDB
N-(17Z-Hexacosenoyl)-D-erythro-sphinganineHMDB
Cer(D18:0/26:1(17Z))ChEBI
Chemical FormulaC44H87NO3
Average Molecular Weight678.1665
Monoisotopic Molecular Weight677.668595655
IUPAC Name(17Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]hexacos-17-enamide
Traditional NameC26:1DH cer
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H87NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-44(48)45-42(41-46)43(47)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h17-18,42-43,46-47H,3-16,19-41H2,1-2H3,(H,45,48)/b18-17-/t42-,43+/m0/s1
InChI KeyCTSPXOBSUIWAAB-SNMLQRCYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentCeramides
Alternative Parents
Substituents
  • Ceramide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.1e-05 g/LALOGPS
logP10.51ALOGPS
logP15.16ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)13.83ChemAxon
pKa (Strongest Basic)0.034ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity211.94 m³·mol⁻¹ChemAxon
Polarizability93.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+281.88331661259
DarkChem[M-H]-266.56431661259
DeepCCS[M+H]+281.5930932474
DeepCCS[M-H]-279.19530932474
DeepCCS[M-2H]-312.0830932474
DeepCCS[M+Na]+287.50330932474
AllCCS[M+H]+287.432859911
AllCCS[M+H-H2O]+287.132859911
AllCCS[M+NH4]+287.832859911
AllCCS[M+Na]+287.832859911
AllCCS[M-H]-272.232859911
AllCCS[M+Na-2H]-276.632859911
AllCCS[M+HCOO]-281.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cer(d18:0/26:1(17Z))CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC3853.3Standard polar33892256
Cer(d18:0/26:1(17Z))CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC4249.0Standard non polar33892256
Cer(d18:0/26:1(17Z))CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC5264.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cer(d18:0/26:1(17Z)),3TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@@H](CCCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C5047.0Semi standard non polar33892256
Cer(d18:0/26:1(17Z)),3TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@@H](CCCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4713.2Standard non polar33892256
Cer(d18:0/26:1(17Z)),3TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@@H](CCCCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4789.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-4355987000-e4a137b3d30eb83409b72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:0/26:1(17Z)) GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 10V, Positive-QTOFsplash10-03fr-0022009000-98d0faf397501ac3c8252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 20V, Positive-QTOFsplash10-01q9-1196017000-32f5d3fe95ff949cdad82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 40V, Positive-QTOFsplash10-0002-3479151000-5349f07e85e502a2a77c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 10V, Negative-QTOFsplash10-004i-0000009000-aabd27db96459952a3c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 20V, Negative-QTOFsplash10-004i-0034409000-9693e4c270639598fe4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 40V, Negative-QTOFsplash10-01ox-9188000000-4c3e22eeaedbb67c8cc72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 10V, Positive-QTOFsplash10-001i-0000009000-db0e7db2b458c26e0c5f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 20V, Positive-QTOFsplash10-001i-0000009000-db0e7db2b458c26e0c5f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 40V, Positive-QTOFsplash10-014i-0000009000-3eacb775e96413fc24952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 10V, Negative-QTOFsplash10-004i-0000009000-ce52ccd5949c4f7977aa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 20V, Negative-QTOFsplash10-004i-0010009000-66754946823aaf99399b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 40V, Negative-QTOFsplash10-004o-0022009000-15d62360190ee4cf115b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 10V, Positive-QTOFsplash10-004i-0000009000-43e8b87ae8fa46301afa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 20V, Positive-QTOFsplash10-00or-0050009000-713e7fb1f912319c89b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:0/26:1(17Z)) 40V, Positive-QTOFsplash10-02u0-0090005000-a129543a3cdf3cc8ac7d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.031 +/- 0.001 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028442
KNApSAcK IDNot Available
Chemspider ID4446691
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283578
PDB IDNot Available
ChEBI ID74132
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. [PubMed:25935 ]
  2. Tserng KY, Griffin RL: Ceramide metabolite, not intact ceramide molecule, may be responsible for cellular toxicity. Biochem J. 2004 Jun 15;380(Pt 3):715-22. [PubMed:14998372 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  8. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  9. Pruett ST, Bushnev A, Hagedorn K, Adiga M, Haynes CA, Sullards MC, Liotta DC, Merrill AH Jr: Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J Lipid Res. 2008 Aug;49(8):1621-39. doi: 10.1194/jlr.R800012-JLR200. Epub 2008 May 21. [PubMed:18499644 ]
  10. Hannun YA, Obeid LM: Ceramide: an intracellular signal for apoptosis. Trends Biochem Sci. 1995 Feb;20(2):73-7. [PubMed:7701566 ]
  11. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 66 proteins in total.

Enzymes

General function:
Involved in galactosylceramidase activity
Specific function:
Hydrolyzes the galactose ester bonds of galactosylceramide, galactosylsphingosine, lactosylceramide, and monogalactosyldiglyceride. Enzyme with very low activity responsible for the lysosomal catabolism of galactosylceramide, a major lipid in myelin, kidney and epithelial cells of small intestine and colon.
Gene Name:
GALC
Uniprot ID:
P54803
Molecular weight:
77062.86
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:
GBGT1
Uniprot ID:
Q8N5D6
Molecular weight:
40126.9
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in catalytic activity
Specific function:
Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Required for cell growth
Gene Name:
SGMS2
Uniprot ID:
Q8NHU3
Molecular weight:
42279.8
General function:
Involved in catalytic activity
Specific function:
Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Suppresses BAX-mediated apoptosis and also prevents cell death in response to stimuli such as hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. May protect against cell death by reversing the stress-inducible increase in levels of proapoptotic ceramide. Required for cell growth
Gene Name:
SGMS1
Uniprot ID:
Q86VZ5
Molecular weight:
49207.3
General function:
Involved in hydrolase activity
Specific function:
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:
SMPD1
Uniprot ID:
P17405
Molecular weight:
69935.53
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
Gene Name:
UGCG
Uniprot ID:
Q16739
Molecular weight:
44853.255
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q14442
Molecular weight:
21080.415

Only showing the first 10 proteins. There are 66 proteins in total.