Bovine Metabolome Database: Showing metabocard for PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0008412)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:20:48 UTC

Update Date

2020-05-11 18:45:28 UTC

BMDB ID

BMDB0008412

Secondary Accession Numbers

BMDB08412

Metabolite Identification

Common Name

PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))

Description

PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)), also known as pc(20:3(8z,11z,14z)/20:5(5z,8z,11z,14z,17z)) or PC(40:8), 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. Thus, PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-choline and DG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) and L-serine can be converted into choline and PS(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Homo-g-linolenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine	HMDB
Phosphatidylcholine(20:3/20:5)	HMDB
PC(40:8)	HMDB
GPCho(20:3/20:5)	HMDB
Phosphatidylcholine(40:8)	HMDB
Lecithin	HMDB
GPCho(40:8)	HMDB
1-(8Z,11Z,14Z-Eicosatrienoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(20:3/20:5)	HMDB
PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))	Lipid Annotator

Chemical Formula

C₄₈H₈₀NO₈P

Average Molecular Weight

830.1245

Monoisotopic Molecular Weight

829.562155053

IUPAC Name

(2-{[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C48H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,14-17,20-23,26-29,33,35,46H,6-8,10,12-13,18-19,24-25,30-32,34,36-45H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,35-33-/t46-/m1/s1

InChI Key

HPXVUIIWTAPGLC-IBSYIIJISA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphocholines (LMGP01011890 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Intracellular membrane
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
logP	5.63	ALOGPS
logP	8.77	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	261.61 m³·mol⁻¹	ChemAxon
Polarizability	96.76 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-6b9fc011848cc9c89204	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-2474fb0095b51b5e823c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041120-9d2bebd454afee3dc8d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-1057516eaf51445afea3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-4e0b1f0b79372e5fc6ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-1900041120-077321fe5d461153caf6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000090-fa2bf6c3c89cea47a840	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0029003370-5d05c71b88b1910973f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5159000000-24ce04fddb8b3e2d322c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-1023bafff7fb8b4a46bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000000190-4a5c55b4ef6aa69ab843	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-0200498220-6458a8ef3141f3b16a00	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000090-cb15d5da1da59dd58588	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000190-ee3451433bac9c082aa2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014k-0900369110-42f982f0bcb0916f2b43	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000090-f258085e9de304c2430e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0003000090-9a24133666ef96363acf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-17vi-0009000040-80a70c848338029adade	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))		Not Available