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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-11 21:57:19 UTC
Update Date2021-10-27 23:23:57 UTC
HMDB IDHMDB0061455
Secondary Accession Numbers
  • HMDB61455
Metabolite Identification
Common NamePC(MonoMe(13,5)/DiMe(13,5))
DescriptionPC(MonoMe(13,5)/DiMe(13,5)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(MonoMe(13,5)/DiMe(13,5)), in particular, consists of one chain of 14,17-epoxy-15,16-dimethyldocosa-14,16-dienoic at the C-1 position and one chain of 14,17-epoxy-15-methyldocosa-14,16-dienoic at the C-2 position. The 14,17-epoxy-15,16-dimethyldocosa-14,16-dienoic moiety is derived from X, while the 14,17-epoxy-15-methyldocosa-14,16-dienoic moiety is derived from fish oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Data?1563866188
Synonyms
ValueSource
PC(MonoMe(13,5)/DiMe(13,5))SMPDB
Phosphatidylcholine(13M5/13D5)SMPDB
Phosphatidylcholine(MonoMe(13,5)/DiMe(13,5))SMPDB
PC(13M5/13D5)SMPDB
Chemical FormulaC55H99NO10P
Average Molecular Weight965.349
Monoisotopic Molecular Weight964.700659905
IUPAC Name(2-{[13-(3,4-dimethyl-5-pentylfuran-2-yl)tridecanoyl]oxy}-3-{[13-(3-methyl-5-pentylfuran-2-yl)tridecanoyl]oxy}propoxy)[2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional Name2-{[13-(3,4-dimethyl-5-pentylfuran-2-yl)tridecanoyl]oxy}-3-{[13-(3-methyl-5-pentylfuran-2-yl)tridecanoyl]oxy}propoxy(2-(trimethylammonio)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H]C1=C(CCCCC)OC(CCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC2=C(C)C(C)=C(CCCCC)O2)=C1C
InChI Identifier
InChI=1S/C55H98NO10P/c1-9-11-29-35-49-43-46(3)51(64-49)36-31-25-21-17-13-15-19-23-27-33-39-54(57)61-44-50(45-63-67(59,60)62-42-41-56(6,7)8)65-55(58)40-34-28-24-20-16-14-18-22-26-32-38-53-48(5)47(4)52(66-53)37-30-12-10-2/h43,50H,9-42,44-45H2,1-8H3/p+1
InChI KeyJPXWGKKIQVJFMS-UHFFFAOYSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Furanoid fatty acid
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Furan
  • Tetraalkylammonium salt
  • Heteroaromatic compound
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic salt
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

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 Solubility0.0016 g/LALOGPS
logP10(6.04) g/LALOGPS
logP10(12.06) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area134.64 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity285.94 m³·mol⁻¹ChemAxon
Polarizability121.06 ųChemAxon
Number of Rings2ChemAxon
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]+328.36831661259
DarkChem[M-H]-305.96531661259
DeepCCS[M+H]+316.1330932474
DeepCCS[M-H]-314.30630932474
DeepCCS[M-2H]-347.89230932474
DeepCCS[M+Na]+321.73630932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 10V, Positive-QTOFsplash10-03di-0000000009-af7dedfed4223335b0692017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 20V, Positive-QTOFsplash10-03e9-0600000009-91848291008c2f2e86f32017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 40V, Positive-QTOFsplash10-001i-1900013103-345266abdc5c0272a9be2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 10V, Positive-QTOFsplash10-00di-0000000009-8fbc775f2e8eafb230e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 20V, Positive-QTOFsplash10-00di-0000000009-3f7a92c68b5221abfa242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 40V, Positive-QTOFsplash10-01wr-0200066904-3bd02626b4d52c0b20c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 10V, Positive-QTOFsplash10-03di-0000000009-c49fba01812c3bce0b442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 20V, Positive-QTOFsplash10-03e9-0600000009-d6b86dda2487402326272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 40V, Positive-QTOFsplash10-001i-1900013103-1c1926417d40c94ed6fd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 10V, Negative-QTOFsplash10-0002-0000000009-3e616e7082fe56b068c52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 20V, Negative-QTOFsplash10-0002-0003000009-4a4b974a92928ee422d42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 40V, Negative-QTOFsplash10-03i2-0009000004-06caac2af567e22170fb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 10V, Positive-QTOFsplash10-000i-0000000009-caad606eeb825c6f3d062021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 20V, Positive-QTOFsplash10-000i-0000000009-23205ce33cb6c87360ee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(MonoMe(13,5)/DiMe(13,5)) 40V, Positive-QTOFsplash10-0f6t-0900036093-e6e2f1ca441c7a387f932021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
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. Wang Z, Klipfell E, Bennett BJ, Koeth R, Levison BS, Dugar B, Feldstein AE, Britt EB, Fu X, Chung YM, Wu Y, Schauer P, Smith JD, Allayee H, Tang WH, DiDonato JA, Lusis AJ, Hazen SL: Gut flora metabolism of phosphatidylcholine promotes cardiovascular disease. Nature. 2011 Apr 7;472(7341):57-63. doi: 10.1038/nature09922. [PubMed:21475195 ]
  2. Spiteller G: Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids. 2005 Aug;40(8):755-71. [PubMed:16296395 ]
  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. Furse S, de Kroon AI: Phosphatidylcholine's functions beyond that of a membrane brick. Mol Membr Biol. 2015;32(4):117-9. doi: 10.3109/09687688.2015.1066894. Epub 2015 Aug 25. [PubMed:26306852 ]
  9. Exton JH: Signaling through phosphatidylcholine breakdown. J Biol Chem. 1990 Jan 5;265(1):1-4. [PubMed:2104616 ]
  10. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  12. Li, Zhaoyu, and Dennis E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylcholine and choline homeostasis. Journal of Lipid Research.
  13. The AOCS Lipid Library [Link]

Only showing the first 10 proteins. There are 78 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
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.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
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 phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:
ABCB4
Uniprot ID:
P21439
Molecular weight:
141521.8

Only showing the first 10 proteins. There are 78 proteins in total.