Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-07-07 20:53:56 UTC
HMDB IDHMDB0004953
Secondary Accession Numbers
  • HMDB04953
Metabolite Identification
Common NameCer(d18:1/24:1)
DescriptionCer(d18:1/24:1(15Z)), also known as N-15Z-tetracosenoyl-sphing-4-enine, 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(d18:1/24:1(15Z)) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached unsaturated 15Z-tetracosenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Data?1582752333
Synonyms
ValueSource
C24:1 CerChEBI
Ceramide (D18:1/24:1(15Z))ChEBI
N-(15-cis)-TetracosenoylsphingosineChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enineChEBI
N-(15Z-Tetracosenoyl)ceramideChEBI
N-(15Z-Tetracosenoyl)sphing-4-enineChEBI
N-NervonylsphingosineChEBI
(2S,3R,4E)-2-Acylamino-1,3-octadec-4-enediolHMDB
(2S,3R,4E)-2-Acylaminooctadec-4-ene-1,3-diolHMDB
CerHMDB
CeramideHMDB
N-AcylsphingosineHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamideHMDB
Ceramide(D18:1/24:1(15Z))HMDB
N-(15Z-Tetracosenoyl)-sphingosineHMDB
N-(15Z-Tetracosenoyl)-D-erythro-sphingosineHMDB
N-(15Z-Tetracosenoyl)-4-sphingenineHMDB
N-(15Z-Tetracosenoyl)-D-sphingosineHMDB
N-(15Z-Tetracosenoyl)-sphingenineHMDB
N-(15Z-Tetracosenoyl)-erythro-4-sphingenineHMDB
Cer(D18:1/24:1(15Z))ChEBI
Chemical FormulaC42H81NO3
Average Molecular Weight648.0974
Monoisotopic Molecular Weight647.621645463
IUPAC Name(15Z)-N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracos-15-enamide
Traditional NameN-(15Z-tetracosenoyl)-ceramide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H81NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h17-18,35,37,40-41,44-45H,3-16,19-34,36,38-39H2,1-2H3,(H,43,46)/b18-17-,37-35+/t40-,41+/m0/s1
InChI KeyVJSBNBBOSZJDKB-KPEYJIHVSA-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
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP10.44ALOGPS
logP14.06ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity203.7 m³·mol⁻¹ChemAxon
Polarizability88.78 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]+272.42131661259
DarkChem[M-H]-263.72731661259
DeepCCS[M+H]+274.77530932474
DeepCCS[M-H]-272.3830932474
DeepCCS[M-2H]-305.26430932474
DeepCCS[M+Na]+280.68830932474
AllCCS[M+H]+278.032859911
AllCCS[M+H-H2O]+277.632859911
AllCCS[M+NH4]+278.432859911
AllCCS[M+Na]+278.532859911
AllCCS[M-H]-263.732859911
AllCCS[M+Na-2H]-269.032859911
AllCCS[M+HCOO]-275.032859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cer(d18:1/24:1(15Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C5023.3Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C4606.6Standard non polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C5022.2Standard polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC4999.2Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC4677.7Standard non polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC5285.6Standard polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C4852.3Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C4641.2Standard non polar33892256
Cer(d18:1/24:1(15Z)),1TMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C5308.6Standard polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C4946.3Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C4483.3Standard non polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C4691.1Standard polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4833.8Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4493.9Standard non polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4759.6Standard polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C4807.6Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C4555.3Standard non polar33892256
Cer(d18:1/24:1(15Z)),2TMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C5022.4Standard polar33892256
Cer(d18:1/24:1(15Z)),3TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4817.6Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),3TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4486.9Standard non polar33892256
Cer(d18:1/24:1(15Z)),3TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C)[Si](C)(C)C4488.9Standard polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C5243.2Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C4698.0Standard non polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C5019.5Standard polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC5237.0Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC4779.7Standard non polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC5252.8Standard polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5078.5Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C4738.0Standard non polar33892256
Cer(d18:1/24:1(15Z)),1TBDMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5265.3Standard polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C5433.4Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C4714.9Standard non polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C4773.5Standard polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C5290.7Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4736.8Standard non polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4839.8Standard polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5268.8Semi standard non polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C4778.8Standard non polar33892256
Cer(d18:1/24:1(15Z)),2TBDMS,isomer #3CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/CCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5058.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cer(d18:1/24:1) GC-MS (TMS_3_1) - 70eV, PositiveNot Available2022-08-08Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 10V, Positive-QTOFsplash10-0002-0000009000-1f40f0f6aabd3d3778222017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 20V, Positive-QTOFsplash10-01ot-0050009000-2c2c621fcd34db4a00c62017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 40V, Positive-QTOFsplash10-01q9-0090006000-76fbd24c138f61a26c692017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 10V, Positive-QTOFsplash10-0udi-0000009000-31264534e837f791da652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 20V, Positive-QTOFsplash10-0udi-0000009000-31264534e837f791da652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 40V, Positive-QTOFsplash10-000i-0000009000-68b46d0682c146d495b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 10V, Negative-QTOFsplash10-0002-0000009000-99b30254d9b8ff6d778b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 20V, Negative-QTOFsplash10-0002-0010009000-e0f0fb15548876ff5fcc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 40V, Negative-QTOFsplash10-01ot-0022009000-9cde7a2c939063482b602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 10V, Positive-QTOFsplash10-0002-0000009000-8034b399a95d3586d3662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 20V, Positive-QTOFsplash10-01ot-0050009000-60034ad5862116f2cc772021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:1/24:1) 40V, Positive-QTOFsplash10-01q9-0090006000-6bfbef23ab00b1bb555b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1 +/- 0.029 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023540
KNApSAcK IDNot Available
Chemspider ID4446681
KEGG Compound IDC00195
BioCyc IDCERAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7206
PubChem Compound5283568
PDB IDNot Available
ChEBI ID74450
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. Erdreich-Epstein A, Tran LB, Cox OT, Huang EY, Laug WE, Shimada H, Millard M: Endothelial apoptosis induced by inhibition of integrins alphavbeta3 and alphavbeta5 involves ceramide metabolic pathways. Blood. 2005 Jun 1;105(11):4353-61. Epub 2005 Feb 10. [PubMed:15705795 ]
  2. Guchhait P, Lopez JA, Thiagarajan P: Characterization of autoantibodies against sulfatide from a V-gene phage-display library derived from patients with systemic lupus erythematosus. J Immunol Methods. 2004 Dec;295(1-2):129-37. Epub 2004 Oct 26. [PubMed:15627618 ]
  3. Ogawa-Goto K, Ohta Y, Kubota K, Funamoto N, Abe T, Taki T, Nagashima K: Glycosphingolipids of human peripheral nervous system myelins isolated from cauda equina. J Neurochem. 1993 Oct;61(4):1398-403. [PubMed:7690848 ]
  4. Deguchi H, Yegneswaran S, Griffin JH: Sphingolipids as bioactive regulators of thrombin generation. J Biol Chem. 2004 Mar 26;279(13):12036-42. Epub 2004 Jan 13. [PubMed:14722105 ]
  5. Holleran WM, Ginns EI, Menon GK, Grundmann JU, Fartasch M, McKinney CE, Elias PM, Sidransky E: Consequences of beta-glucocerebrosidase deficiency in epidermis. Ultrastructure and permeability barrier alterations in Gaucher disease. J Clin Invest. 1994 Apr;93(4):1756-64. [PubMed:8163674 ]
  6. Saito M, Saito M, Cooper TB, Vadasz C: Ethanol-induced changes in the content of triglycerides, ceramides, and glucosylceramides in cultured neurons. Alcohol Clin Exp Res. 2005 Aug;29(8):1374-83. [PubMed:16131844 ]
  7. Garcia-Ruiz C, Mari M, Morales A, Colell A, Ardite E, Fernandez-Checa JC: Human placenta sphingomyelinase, an exogenous acidic pH-optimum sphingomyelinase, induces oxidative stress, glutathione depletion, and apoptosis in rat hepatocytes. Hepatology. 2000 Jul;32(1):56-65. [PubMed:10869289 ]
  8. van Lijnschoten G, Groener JE, Maas SM, Ben-Yoseph Y, Dingemans KP, Offerhaus GJ: Intrauterine fetal death due to Farber disease: case report. Pediatr Dev Pathol. 2000 Nov-Dec;3(6):597-602. [PubMed:11000338 ]
  9. Maurer BJ, Melton L, Billups C, Cabot MC, Reynolds CP: Synergistic cytotoxicity in solid tumor cell lines between N-(4-hydroxyphenyl)retinamide and modulators of ceramide metabolism. J Natl Cancer Inst. 2000 Dec 6;92(23):1897-909. [PubMed:11106681 ]
  10. Poliak S, Gollan L, Salomon D, Berglund EO, Ohara R, Ranscht B, Peles E: Localization of Caspr2 in myelinated nerves depends on axon-glia interactions and the generation of barriers along the axon. J Neurosci. 2001 Oct 1;21(19):7568-75. [PubMed:11567047 ]
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Only showing the first 10 proteins. There are 70 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61
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 hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
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

Only showing the first 10 proteins. There are 70 proteins in total.