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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-26 14:11:35 UTC
Update Date2022-03-07 02:51:02 UTC
HMDB IDHMDB0010700
Secondary Accession Numbers
  • HMDB10700
Metabolite Identification
Common NameCerP(d18:1/16:0)
DescriptionCerP(d18:1/16:0), also known as N-hexadecanoyl-sphing-4-enine-1-phosphate, is a ceramide phosphate (CerP). Ceramide phosphates 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, ceramide phosphate are formed from ceramides by the action of a specific ceramide kinase (CerK) and can be dephosphorylated by phosphatidate phosphatase back to the ceramide. CerPs are an important metabolite of ceramide as it acts as a mediator of the inflammatory response. CerPs are also known to have a dual regulatory capacity acting as intracellular second messengers to regulate cell survival, or as extracellular receptor ligands to stimulate chemotaxis. Moreover, CerPs have been shown to be specific and potent inducers of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of cytoplasmic phospholipase A2. In terms of its appearance and structure, CerP(d18:1/16:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated hexadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Data?1582752862
Synonyms
ValueSource
N-Hexadecanoylsphing-4-enine-1-phosphateChEBI
N-Palmitoylsphing-4-enine-1-phosphateChEBI
N-Palmitoylsphingosine 1-phosphateChEBI
N-Hexadecanoylsphing-4-enine-1-phosphoric acidGenerator
N-Palmitoylsphing-4-enine-1-phosphoric acidGenerator
N-Palmitoylsphingosine 1-phosphoric acidGenerator
Ceramide phosphateMetBuilder
N-(Hexadecanoyl)-1-phosphate-sphing-4-enineMetBuilder
Ceramide phosphate(D18:1/16:0)MetBuilder
N-(Hexadecanoyl)-1-phosphate-sphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-D-erythro-sphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-4-sphingenineMetBuilder
N-(Hexadecanoyl)-1-phosphate-D-sphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-sphingenineMetBuilder
N-(Hexadecanoyl)-1-phosphate-erythro-4-sphingenineMetBuilder
N-(Hexadecanoyl)-sphing-4-enine-1-phosphateHMDB
[(e,2S,3R)-2-(hexadecanoylamino)-3-Hydroxyoctadec-4-enyl] dihydrogen phosphateHMDB
Chemical FormulaC34H68NO6P
Average Molecular Weight617.8806
Monoisotopic Molecular Weight617.478425425
IUPAC Name{[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
Traditional NameC16 CerP
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C34H68NO6P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(36)32(31-41-42(38,39)40)35-34(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36H,3-26,28,30-31H2,1-2H3,(H,35,37)(H2,38,39,40)/b29-27+/t32-,33+/m0/s1
InChI KeyUNRULDRRONAKLU-TURZORIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
Substituents
  • Sphingoid-1-phosphate or derivatives
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Fatty amide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
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 Solubility0.0001 g/LALOGPS
logP8.24ALOGPS
logP10.58ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.53ChemAxon
pKa (Strongest Basic)0.00068ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.09 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity176.65 m³·mol⁻¹ChemAxon
Polarizability78.06 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]+257.22431661259
DarkChem[M-H]-251.44131661259
DeepCCS[M+H]+262.56430932474
DeepCCS[M-H]-260.66930932474
DeepCCS[M-2H]-293.9130932474
DeepCCS[M+Na]+268.99430932474
AllCCS[M+H]+265.732859911
AllCCS[M+H-H2O]+265.132859911
AllCCS[M+NH4]+266.132859911
AllCCS[M+Na]+266.332859911
AllCCS[M-H]-251.032859911
AllCCS[M+Na-2H]-255.332859911
AllCCS[M+HCOO]-260.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CerP(d18:1/16:0)CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC4411.2Standard polar33892256
CerP(d18:1/16:0)CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC3993.0Standard non polar33892256
CerP(d18:1/16:0)CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC4775.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
CerP(d18:1/16:0),1TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)NC(=O)CCCCCCCCCCCCCCC4540.3Semi standard non polar33892256
CerP(d18:1/16:0),1TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4532.1Semi standard non polar33892256
CerP(d18:1/16:0),1TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4476.9Semi standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4488.6Semi standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4147.0Standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC5249.0Standard polar33892256
CerP(d18:1/16:0),2TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4530.4Semi standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4158.0Standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C5675.3Standard polar33892256
CerP(d18:1/16:0),2TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4473.5Semi standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4252.2Standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC5078.7Standard polar33892256
CerP(d18:1/16:0),2TMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4498.9Semi standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4227.8Standard non polar33892256
CerP(d18:1/16:0),2TMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C5412.1Standard polar33892256
CerP(d18:1/16:0),3TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4489.6Semi standard non polar33892256
CerP(d18:1/16:0),3TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4128.7Standard non polar33892256
CerP(d18:1/16:0),3TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCC4641.2Standard polar33892256
CerP(d18:1/16:0),3TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4510.5Semi standard non polar33892256
CerP(d18:1/16:0),3TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4164.8Standard non polar33892256
CerP(d18:1/16:0),3TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4948.3Standard polar33892256
CerP(d18:1/16:0),3TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4457.8Semi standard non polar33892256
CerP(d18:1/16:0),3TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4220.4Standard non polar33892256
CerP(d18:1/16:0),3TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C4844.1Standard polar33892256
CerP(d18:1/16:0),1TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)NC(=O)CCCCCCCCCCCCCCC4823.2Semi standard non polar33892256
CerP(d18:1/16:0),1TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC4804.8Semi standard non polar33892256
CerP(d18:1/16:0),1TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C4723.1Semi standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC5053.5Semi standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC4406.3Standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC5202.6Standard polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5005.5Semi standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C4440.0Standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5523.9Standard polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC5066.5Semi standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC4452.8Standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)NC(=O)CCCCCCCCCCCCCCC5124.2Standard polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C4942.1Semi standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C4492.1Standard non polar33892256
CerP(d18:1/16:0),2TBDMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCCCCCCCCCCCCCC)[Si](C)(C)C(C)(C)C5358.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS (1 TMS) - 70eV, Positivesplash10-022a-9114256000-70029283243742b63ffc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - CerP(d18:1/16:0) GC-MS ("CerP(d18:1/16:0),1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CerP(d18:1/16:0) 10V, Negative-QTOFsplash10-014i-2000009000-9b49d4a6a5e50d9a0bfa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CerP(d18:1/16:0) 20V, Negative-QTOFsplash10-016r-9000007000-da48a526484a4a6e0f262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CerP(d18:1/16:0) 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CerP(d18:1/16:0) 10V, Positive-QTOFsplash10-00xr-0000197000-ca8198b56f63cdf300892021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CerP(d18:1/16:0) 20V, Positive-QTOFsplash10-0uk9-0010092000-ee5db710d22114fccbec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CerP(d18:1/16:0) 40V, Positive-QTOFsplash10-014i-4590000000-a35ff7a144ee7bc18e022021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027850
KNApSAcK IDNot Available
Chemspider ID4446694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283581
PDB ID1PX
ChEBI ID73145
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. 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 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.