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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:06:31 UTC
Update Date2021-10-01 18:39:43 UTC
HMDB IDHMDB0243890
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-O-Hexadecyl-sn-glycero-3-phosphocholine
Description(2-{[3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium, also known as 1-O-hexadecyl-2-lyso-sn-glycero-3-phosphocholine, belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond. Based on a literature review very few articles have been published on (2-{[3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-o-hexadecyl-sn-glycero-3-phosphocholine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-O-Hexadecyl-sn-glycero-3-phosphocholine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1-O-Hexadecyl-2-lyso-sn-glycero-3-phosphocholineKegg
Chemical FormulaC24H52NO6P
Average Molecular Weight481.655
Monoisotopic Molecular Weight481.353225396
IUPAC Name(2-{[3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCOCC(O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3
InChI KeyVLBPIWYTPAXCFJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentMonoalkylglycerophosphocholines
Alternative Parents
Substituents
  • Monoalkylglycerophosphocholine
  • Phosphocholine
  • Glycerol ether
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP2.36ALOGPS
logP1.57ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.05 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity142.52 m³·mol⁻¹ChemAxon
Polarizability59.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+219.54530932474
DeepCCS[M-H]-215.52530932474
DeepCCS[M-2H]-252.06830932474
DeepCCS[M+Na]+228.3630932474
AllCCS[M+H]+231.732859911
AllCCS[M+H-H2O]+230.332859911
AllCCS[M+NH4]+233.032859911
AllCCS[M+Na]+233.332859911
AllCCS[M-H]-227.232859911
AllCCS[M+Na-2H]-229.332859911
AllCCS[M+HCOO]-231.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-O-Hexadecyl-sn-glycero-3-phosphocholineCCCCCCCCCCCCCCCCOCC(O)COP([O-])(=O)OCC[N+](C)(C)C3262.4Standard polar33892256
1-O-Hexadecyl-sn-glycero-3-phosphocholineCCCCCCCCCCCCCCCCOCC(O)COP([O-])(=O)OCC[N+](C)(C)C3007.1Standard non polar33892256
1-O-Hexadecyl-sn-glycero-3-phosphocholineCCCCCCCCCCCCCCCCOCC(O)COP([O-])(=O)OCC[N+](C)(C)C3203.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0032-4960000000-2ff8def4f9b9c6c306b62016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 10V, Positive-QTOFsplash10-0019-9151400000-842fb747b8d4191ed2182019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 20V, Positive-QTOFsplash10-005i-7291100000-b36af285768bf13dfb272019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 40V, Positive-QTOFsplash10-003i-9340000000-77e3b535d064fb67cb082019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 10V, Negative-QTOFsplash10-001i-0022900000-f5ab01d20344323d020d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 20V, Negative-QTOFsplash10-00bd-2198300000-2efdef904a224eb0ab272019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 40V, Negative-QTOFsplash10-004l-8291000000-b027520e261dd7d2aa5c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 10V, Negative-QTOFsplash10-014i-0000090000-3636af85e402969cdf042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 20V, Negative-QTOFsplash10-014i-0110690000-2d0435840a9fe716e1a62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 40V, Negative-QTOFsplash10-014i-0113910000-5a74ded8418eec7903822021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 10V, Positive-QTOFsplash10-001i-1900700000-2656ab57af11e93094a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 20V, Positive-QTOFsplash10-0f89-1610900000-26478851e66979dd8fe72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 40V, Positive-QTOFsplash10-0f89-0610900000-6b5800738e32be035b5e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 10V, Positive-QTOFsplash10-0udi-0000090000-186fe8833c5951767f002021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 20V, Positive-QTOFsplash10-0udi-0000090000-186fe8833c5951767f002021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-O-Hexadecyl-sn-glycero-3-phosphocholine 40V, Positive-QTOFsplash10-0002-0000910000-4863de933aa5fa2f7c532021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3845
KEGG Compound IDC13903
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:
ENPP2
Uniprot ID:
Q13822
Molecular weight:
98992.78
General function:
Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:
Modulates the action of platelet-activating factor (PAF) by hydrolyzing the sn-2 ester bond to yield the biologically inactive lyso-PAF. Has a specificity for substrates with a short residue at the sn-2 position. It is inactive against long-chain phospholipids.
Gene Name:
PLA2G7
Uniprot ID:
Q13093
Molecular weight:
50076.99
General function:
Involved in hydrolase activity
Specific function:
Inactivates paf by removing the acetyl group at the sn-2 position. This is a catalytic subunit. Plays an important role during the development of brain.
Gene Name:
PAFAH1B3
Uniprot ID:
Q15102
Molecular weight:
25734.13
General function:
Involved in metabolic process
Specific function:
Has a preference for arachidonic acid at the sn-2 position of phosphatidylcholine as compared with palmitic acid.
Gene Name:
PLA2G4C
Uniprot ID:
Q9UP65
Molecular weight:
60938.07
General function:
Involved in hydrolase activity
Specific function:
Inactivates PAF by removing the acetyl group at the sn-2 position. This is a catalytic subunit.
Gene Name:
PAFAH1B2
Uniprot ID:
P68402
Molecular weight:
22733.715
General function:
Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:
Has a marked selectivity for phospholipids with short acyl chains at the sn-2 position. May share a common physiologic function with the plasma-type enzyme.
Gene Name:
PAFAH2
Uniprot ID:
Q99487
Molecular weight:
44035.255
General function:
Involved in metal ion binding
Specific function:
Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:
SMPD2
Uniprot ID:
O60906
Molecular weight:
47645.29

Only showing the first 10 proteins. There are 23 proteins in total.