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Human Metabolome Database Version 3.5

Showing metabocard for PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (HMDB08518)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (77) transporters (1)

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2008-09-11 19:38:23 -0600
Update Date	2013-02-08 17:19:42 -0700
HMDB ID	HMDB08518
Secondary Accession Numbers	None
Metabolite Identification
Common Name	PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Description	PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The eicosapentaenoic acid moiety is derived from fish oils, liver and kidney, while the docosahexaenoic acid moiety is derived from fish oils. 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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	1-Eicosapentaenoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine GPCho(20:5/22:6) GPCho(20:5n3/22:6n3) GPCho(20:5w3/22:6w3) GPCho(42:11) Lecithin PC(20:5/22:6) PC(20:5n3/22:6n3) PC(20:5w3/22:6w3) PC(42:11) Phosphatidylcholine(20:5/22:6) Phosphatidylcholine(20:5n3/22:6n3) Phosphatidylcholine(20:5w3/22:6w3) Phosphatidylcholine(42:11)
Chemical Formula	C50H78NO8P
Average Molecular Weight	852.13
Monoisotopic Molecular Weight	851.546504989
IUPAC Name	(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name	(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry Number	Not Available
SMILES	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier	InChI=1S/C50H78NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,25,27-28,30-31,33-34,36-37,39,48H,6-7,12-13,18-19,24,26,29,32,35,38,40-47H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,27-25-,30-28-,33-31-,36-34-,39-37-/t48-/m1/s1
InChI Key	PRAHGYJIPXTSPA-OWXGTRINSA-N
Chemical Taxonomy
Kingdom	Organic Compounds
Super Class	Lipids
Class	Glycerophospholipids
Sub Class	Glycerophosphocholines
Other Descriptors	Aliphatic Acyclic Compounds
Substituents	Acyclic Alkene Carboxylic Acid Ester Choline Dicarboxylic Acid Derivative Fatty Acid Ester Glycero 3 Phosphocholine Organic Hypophosphite Organic Phosphite Phosphocholine Phosphoethanolamine Phosphoric Acid Ester Quaternary Ammonium Salt
Direct Parent	Phosphatidylcholines
Ontology
Status	Expected and Not Quantified
Origin	Endogenous Food
Biofunction	Cell signaling Energy source Fuel and energy storage Fuel or energy source Membrane component Membrane integrity/stability
Application	Nutrients Stabilizers Surfactants and Emulsifiers
Cellular locations	Extracellular Membrane
Physical Properties
State	Solid
Experimental Properties	Property Value Reference Melting Point Not Available Not Available Boiling Point Not Available Not Available Water Solubility Not Available Not Available LogP Not Available Not Available
Predicted Properties	Property Value Source Water Solubility 4.720E-05 g/L ALOGPS LogP 5.47 ALOGPS LogP 8.58 ChemAxon LogS -7.28 ALOGPS pKa (strongest acidic) 1.86 ChemAxon pKa (strongest basic) -6.7 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 111.19 A2 ChemAxon Rotatable Bond Count 39 ChemAxon Refractivity 274.16 ChemAxon Polarizability 96.87 ChemAxon Formal Charge 0 ChemAxon Physiological Charge 0 ChemAxon
Spectra
	Not Available
Biological Properties
Cellular Locations	Extracellular Membrane
Biofluid Locations	Not Available
Tissue Location	All Tissues
Pathways	Not Available
Normal Concentrations
	Not Available
Abnormal Concentrations
	Not Available
Predicted Concentrations
	Biofluid Value Original age Original sex Original condition Comments Blood 1.537725048 +/- 0.42423541 uM Adult (>18 years old) Both Normal (Most Probable) Calculated using MetaboAnalyst Blood 61.1 +/- 14.12657071 uM Adult (>18 years old) Both Normal (Upper Limit) Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
DrugBank Metabolite ID	Not Available
Phenol Explorer Compound ID	Not Available
Phenol Explorer Metabolite ID	Not Available
FoodDB ID	FDB025708
KNApSAcK ID	Not Available
Chemspider ID	24767179
KEGG Compound ID	C00157
BioCyc ID	PHOSPHATIDYLCHOLINE
BiGG ID	Not Available
Wikipedia Link	Lecithin
NuGOwiki Link	HMDB08518
Metagene Link	HMDB08518
METLIN ID	Not Available
PubChem Compound	24779082
PDB ID	Not Available
ChEBI ID	Not Available
References
Synthesis Reference	Not Available
Material Safety Data Sheet (MSDS)	Not Available
General References	Not Available

---

Enzymes
Name: Acyl-protein thioesterase 1 Reactions: Not Available Gene Name: LYPLA1 Uniprot ID: O75608 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group XV phospholipase A2 Reactions: Not Available Gene Name: PLA2G15 Uniprot ID: Q8NCC3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Calcium-dependent phospholipase A2 Reactions: Not Available Gene Name: PLA2G5 Uniprot ID: P39877 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G2F Uniprot ID: Q9BZM2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 Reactions: Not Available Gene Name: PLA2G4A Uniprot ID: P47712 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase A2 Reactions: Not Available Gene Name: PLA2G1B Uniprot ID: P04054 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group XIIB secretory phospholipase A2-like protein Reactions: Not Available Gene Name: PLA2G12B Uniprot ID: Q9BX93 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G10 Uniprot ID: O15496 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G2E Uniprot ID: Q9NZK7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Acyl-protein thioesterase 2 Reactions: Not Available Gene Name: LYPLA2 Uniprot ID: O95372 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group XIIA secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G12A Uniprot ID: Q9BZM1 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2 Reactions: Not Available Gene Name: PLA2G6 Uniprot ID: O60733 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylcholine-sterol acyltransferase Reactions: Not Available Gene Name: LCAT Uniprot ID: P04180 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Eosinophil lysophospholipase Reactions: Not Available Gene Name: CLC Uniprot ID: Q05315 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase A2, membrane associated Reactions: Not Available Gene Name: PLA2G2A Uniprot ID: P14555 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G2D Uniprot ID: Q9UNK4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase D2 Reactions: Not Available Gene Name: PLD2 Uniprot ID: O14939 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylethanolamine N-methyltransferase Reactions: Not Available Gene Name: PEMT Uniprot ID: Q9UBM1 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase D1 Reactions: Not Available Gene Name: PLD1 Uniprot ID: Q13393 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 gamma Reactions: Not Available Gene Name: PLA2G4C Uniprot ID: Q9UP65 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G3 Uniprot ID: Q9NZ20 Protein Sequence: FASTA Gene Sequence: FASTA
Name: D-beta-hydroxybutyrate dehydrogenase, mitochondrial Reactions: Not Available Gene Name: BDH1 Uniprot ID: Q02338 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Choline-phosphate cytidylyltransferase B Reactions: Not Available Gene Name: PCYT1B Uniprot ID: Q9Y5K3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Choline-phosphate cytidylyltransferase A Reactions: Not Available Gene Name: PCYT1A Uniprot ID: P49585 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylcholine:ceramide cholinephosphotransferase 2 Reactions: Not Available Gene Name: SGMS2 Uniprot ID: Q8NHU3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylcholine:ceramide cholinephosphotransferase 1 Reactions: Not Available Gene Name: SGMS1 Uniprot ID: Q86VZ5 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Choline kinase alpha Reactions: Not Available Gene Name: CHKA Uniprot ID: P35790 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IG Reactions: Not Available Gene Name: ATP11C Uniprot ID: Q8NB49 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IH Reactions: Not Available Gene Name: ATP11A Uniprot ID: P98196 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VA Reactions: Not Available Gene Name: ATP10A Uniprot ID: O60312 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IC Reactions: Not Available Gene Name: ATP8B1 Uniprot ID: O43520 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IIA Reactions: Not Available Gene Name: ATP9A Uniprot ID: O75110 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VD Reactions: Not Available Gene Name: ATP10D Uniprot ID: Q9P241 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IB Reactions: Not Available Gene Name: ATP8A2 Uniprot ID: Q9NTI2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA Reactions: Not Available Gene Name: ATP8A1 Uniprot ID: Q9Y2Q0 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IM Reactions: Not Available Gene Name: ATP8B4 Uniprot ID: Q8TF62 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IF Reactions: Not Available Gene Name: ATP11B Uniprot ID: Q9Y2G3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IK Reactions: Not Available Gene Name: ATP8B3 Uniprot ID: O60423 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein beta isoform Reactions: Not Available Gene Name: PITPNB Uniprot ID: P48739 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Lecithin retinol acyltransferase Reactions: Not Available Gene Name: LRAT Uniprot ID: O95237 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 1 Reactions: Not Available Gene Name: PLSCR1 Uniprot ID: O15162 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylserine synthase 1 Reactions: Not Available Gene Name: PTDSS1 Uniprot ID: P48651 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein alpha isoform Reactions: Not Available Gene Name: PITPNA Uniprot ID: Q00169 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid transfer protein Reactions: Not Available Gene Name: PLTP Uniprot ID: P55058 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cholinephosphotransferase 1 Reactions: Not Available Gene Name: CHPT1 Uniprot ID: Q8WUD6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2 Reactions: Not Available Gene Name: MOGAT2 Uniprot ID: Q3SYC2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Choline/ethanolaminephosphotransferase 1 Reactions: Not Available Gene Name: CEPT1 Uniprot ID: Q9Y6K0 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3 Reactions: Not Available Gene Name: PLCD3 Uniprot ID: Q8N3E9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Lysophospholipid acyltransferase 5 Reactions: Not Available Gene Name: LPCAT3 Uniprot ID: Q6P1A2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Putative inactive group IIC secretory phospholipase A2 Reactions: Not Available Gene Name: PLA2G2C Uniprot ID: Q5R387 Protein Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 1 Reactions: Not Available Gene Name: LPCAT1 Uniprot ID: Q8NF37 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 2 Reactions: Not Available Gene Name: LPCAT2 Uniprot ID: Q7L5N7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase D3 Reactions: Not Available Gene Name: PLD3 Uniprot ID: Q8IV08 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase D4 Reactions: Not Available Gene Name: PLD4 Uniprot ID: Q96BZ4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylcholine transfer protein Reactions: Not Available Gene Name: PCTP Uniprot ID: Q9UKL6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 2 Reactions: Not Available Gene Name: PLSCR2 Uniprot ID: Q9NRY7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 3 Reactions: Not Available Gene Name: PLSCR3 Uniprot ID: Q9NRY6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 4 Reactions: Not Available Gene Name: PLSCR4 Uniprot ID: Q9NRQ2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase family member 5 Reactions: Not Available Gene Name: PLSCR5 Uniprot ID: A0PG75 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VB Reactions: Not Available Gene Name: ATP10B Uniprot ID: O94823 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase ID Reactions: Not Available Gene Name: ATP8B2 Uniprot ID: P98198 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase B1, membrane-associated Reactions: Not Available Gene Name: PLB1 Uniprot ID: Q6P1J6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylethanolamine-binding protein 1 Reactions: Not Available Gene Name: PEBP1 Uniprot ID: P30086 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylethanolamine-binding protein 4 Reactions: Not Available Gene Name: PEBP4 Uniprot ID: Q96S96 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Membrane-associated phosphatidylinositol transfer protein 1 Reactions: Not Available Gene Name: PITPNM1 Uniprot ID: O00562 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Membrane-associated phosphatidylinositol transfer protein 2 Reactions: Not Available Gene Name: PITPNM2 Uniprot ID: Q9BZ72 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Membrane-associated phosphatidylinositol transfer protein 3 Reactions: Not Available Gene Name: PITPNM3 Uniprot ID: Q9BZ71 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 delta Reactions: Not Available Gene Name: PLA2G4D Uniprot ID: Q86XP0 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 epsilon Reactions: Not Available Gene Name: PLA2G4E Uniprot ID: Q3MJ16 Protein Sequence: FASTA
Name: Cytosolic phospholipase A2 zeta Reactions: Not Available Gene Name: PLA2G4F Uniprot ID: Q68DD2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: ADP-ribosylation factor GTPase-activating protein 1 Reactions: Not Available Gene Name: ARFGAP1 Uniprot ID: Q8N6T3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 beta Reactions: Not Available Gene Name: PLA2G4B Uniprot ID: P0C869 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase D1 variant Reactions: Not Available Gene Name: Not Available Uniprot ID: Q59EA4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase D6 Reactions: Not Available Gene Name: PLD6 Uniprot ID: Q8N2A8 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Neuropathy target esterase Reactions: Not Available Gene Name: PNPLA6 Uniprot ID: Q8IY17 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Apolipoprotein A-V Reactions: Not Available Gene Name: APOA5 Uniprot ID: Q6Q788 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Uteroglobin Reactions: Not Available Gene Name: SCGB1A1 Uniprot ID: P11684 Protein Sequence: FASTA Gene Sequence: FASTA

Transporters
Name: Multidrug resistance protein 3 Reactions: Not Available Gene Name: ABCB4 Uniprot ID: P21439 Protein Sequence: FASTA Gene Sequence: FASTA

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