Human Metabolome Database Version 3.5

Showing metabocard for PC(14:0/15:0) (HMDB07868)

Record Information
Version 3.5
Creation Date 2008-09-11 19:27:27 -0600
Update Date 2013-02-08 17:17:55 -0700
HMDB ID HMDB07868
Secondary Accession Numbers None
Metabolite Identification
Common Name PC(14:0/15:0)
Description PC(14:0/15:0) 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(14:0/15:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the pentadecanoic acid moiety is derived from dairy products and milk fat. 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Myristoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine
  2. GPCho(14:0/15:0)
  3. GPCho(29:0)
  4. Lecithin
  5. PC(14:0/15:0)
  6. PC(29:0)
  7. Phosphatidylcholine(14:0/15:0)
  8. Phosphatidylcholine(29:0)
Chemical Formula C37H74NO8P
Average Molecular Weight 691.9591
Monoisotopic Molecular Weight 691.515204861
IUPAC Name trimethyl(2-{[(2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional IUPAC Name trimethyl(2-{[(2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
CAS Registry Number Not Available
SMILES [H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCC
InChI Identifier InChI=1S/C37H74NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-37(40)46-35(34-45-47(41,42)44-32-31-38(3,4)5)33-43-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h35H,6-34H2,1-5H3/t35-/m1/s1
InChI Key JERIBPHBOOFETI-PGUFJCEWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphocholines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Diacylglycerophosphocholines(Lipidmaps)
Substituents
  • 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 3.370E-05 g/L ALOGPS
LogP 4.76 ALOGPS
LogP 6.78 ChemAxon
LogS -7.34 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 37 ChemAxon
Refractivity 202.06 ChemAxon
Polarizability 84.86 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 Help
Biofluid Value Original age Original sex Original condition Comments
Blood 0.027939066 +/- 0.002849979 uM Adult (>18 years old) Both Normal (Most Probable) Calculated using MetaboAnalyst
Blood 10.56666667 +/- 0.642910051 uM Adult (>18 years old) Both Normal (Upper Limit) Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB025060
KNApSAcK ID Not Available
Chemspider ID 24766546 Link_out
KEGG Compound ID C00157 Link_out
BioCyc ID PHOSPHATIDYLCHOLINE Link_out
BiGG ID Not Available
Wikipedia Link Lecithin Link_out
NuGOwiki Link HMDB07868 Link_out
Metagene Link HMDB07868 Link_out
METLIN ID Not Available
PubChem Compound 24778611 Link_out
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

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 77 enzymes in total.

Name: Acyl-protein thioesterase 1
Reactions: Not Available
Gene Name: LYPLA1
Uniprot ID: O75608 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XV phospholipase A2
Reactions: Not Available
Gene Name: PLA2G15
Uniprot ID: Q8NCC3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-dependent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G5
Uniprot ID: P39877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2F
Uniprot ID: Q9BZM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2
Reactions: Not Available
Gene Name: PLA2G1B
Uniprot ID: P04054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIB secretory phospholipase A2-like protein
Reactions: Not Available
Gene Name: PLA2G12B
Uniprot ID: Q9BX93 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2E
Uniprot ID: Q9NZK7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-protein thioesterase 2
Reactions: Not Available
Gene Name: LYPLA2
Uniprot ID: O95372 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIA secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G12A
Uniprot ID: Q9BZM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylcholine-sterol acyltransferase
Reactions: Not Available
Gene Name: LCAT
Uniprot ID: P04180 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil lysophospholipase
Reactions: Not Available
Gene Name: CLC
Uniprot ID: Q05315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2, membrane associated
Reactions: Not Available
Gene Name: PLA2G2A
Uniprot ID: P14555 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2D
Uniprot ID: Q9UNK4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D2
Reactions: Not Available
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylethanolamine N-methyltransferase
Reactions: Not Available
Gene Name: PEMT
Uniprot ID: Q9UBM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D1
Reactions: Not Available
Gene Name: PLD1
Uniprot ID: Q13393 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 gamma
Reactions: Not Available
Gene Name: PLA2G4C
Uniprot ID: Q9UP65 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G3
Uniprot ID: Q9NZ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D-beta-hydroxybutyrate dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: BDH1
Uniprot ID: Q02338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline-phosphate cytidylyltransferase B
Reactions: Not Available
Gene Name: PCYT1B
Uniprot ID: Q9Y5K3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline-phosphate cytidylyltransferase A
Reactions: Not Available
Gene Name: PCYT1A
Uniprot ID: P49585 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylcholine:ceramide cholinephosphotransferase 2
Reactions: Not Available
Gene Name: SGMS2
Uniprot ID: Q8NHU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylcholine:ceramide cholinephosphotransferase 1
Reactions: Not Available
Gene Name: SGMS1
Uniprot ID: Q86VZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline kinase alpha
Reactions: Not Available
Gene Name: CHKA
Uniprot ID: P35790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IG
Reactions: Not Available
Gene Name: ATP11C
Uniprot ID: Q8NB49 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IH
Reactions: Not Available
Gene Name: ATP11A
Uniprot ID: P98196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VA
Reactions: Not Available
Gene Name: ATP10A
Uniprot ID: O60312 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IC
Reactions: Not Available
Gene Name: ATP8B1
Uniprot ID: O43520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IIA
Reactions: Not Available
Gene Name: ATP9A
Uniprot ID: O75110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VD
Reactions: Not Available
Gene Name: ATP10D
Uniprot ID: Q9P241 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IB
Reactions: Not Available
Gene Name: ATP8A2
Uniprot ID: Q9NTI2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA
Reactions: Not Available
Gene Name: ATP8A1
Uniprot ID: Q9Y2Q0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IM
Reactions: Not Available
Gene Name: ATP8B4
Uniprot ID: Q8TF62 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IF
Reactions: Not Available
Gene Name: ATP11B
Uniprot ID: Q9Y2G3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IK
Reactions: Not Available
Gene Name: ATP8B3
Uniprot ID: O60423 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein beta isoform
Reactions: Not Available
Gene Name: PITPNB
Uniprot ID: P48739 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lecithin retinol acyltransferase
Reactions: Not Available
Gene Name: LRAT
Uniprot ID: O95237 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 1
Reactions: Not Available
Gene Name: PLSCR1
Uniprot ID: O15162 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine synthase 1
Reactions: Not Available
Gene Name: PTDSS1
Uniprot ID: P48651 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein alpha isoform
Reactions: Not Available
Gene Name: PITPNA
Uniprot ID: Q00169 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid transfer protein
Reactions: Not Available
Gene Name: PLTP
Uniprot ID: P55058 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholinephosphotransferase 1
Reactions: Not Available
Gene Name: CHPT1
Uniprot ID: Q8WUD6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2
Reactions: Not Available
Gene Name: MOGAT2
Uniprot ID: Q3SYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline/ethanolaminephosphotransferase 1
Reactions: Not Available
Gene Name: CEPT1
Uniprot ID: Q9Y6K0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3
Reactions: Not Available
Gene Name: PLCD3
Uniprot ID: Q8N3E9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophospholipid acyltransferase 5
Reactions: Not Available
Gene Name: LPCAT3
Uniprot ID: Q6P1A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative inactive group IIC secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2C
Uniprot ID: Q5R387 Link_out
Protein Sequence: FASTA
Transporters
Name: Multidrug resistance protein 3
Reactions: Not Available
Gene Name: ABCB4
Uniprot ID: P21439 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA