Bovine Metabolome Database: Showing metabocard for PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (BMDB0008147)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:14:47 UTC

Update Date

2020-06-04 20:05:07 UTC

BMDB ID

BMDB0008147

Secondary Accession Numbers

BMDB08147

Metabolite Identification

Common Name

PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))

Description

PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)), also known as gpcho(18:2/20:4) or phosphatidylcholine(18:2/20:4), 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(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) and L-serine can be converted into choline and PS(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine	ChEBI
1-Linoleoyl-2-arachidonoyl-GPC	ChEBI
1-Linoleoyl-2-arachidonoyl-GPC (18:2/20:4n6)	ChEBI
GPC(18:2/20:4n6)	ChEBI
GPCho(18:2/20:4)	ChEBI
GPCho(18:2n6/20:4n6)	ChEBI
GPCho(18:2W6/20:4W6)	ChEBI
PC(18:2/20:4)	ChEBI
PC(18:2n6/20:4n6)	ChEBI
PC(18:2W6/20:4W6)	ChEBI
Phosphatidylcholine(18:2/20:4)	ChEBI
Phosphatidylcholine(18:2n6/20:4n6)	ChEBI
Phosphatidylcholine(18:2W6/20:4W6)	ChEBI
1-linoleoyl-2-arachidonoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
Phosphatidylcholine(38:6)	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))	Lipid Annotator
GPCho(38:6)	Lipid Annotator, HMDB
PC(38:6)	Lipid Annotator, HMDB
PC Aa C38:6	HMDB
1-Linoleoyl-2-arachidonoyl-sn-glycero-3-phosphocholine	HMDB
1-Linoleoyl-2-arachidonoyl-sn-glycero-phosphatidylcholine	HMDB
GPC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))	HMDB
GPC(18:2/20:4)	HMDB
GPC(18:2n6/20:4n6)	HMDB
GPC(18:2w6/20:4w6)	HMDB
GPC(38:6)	HMDB
GPCho(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))	HMDB
Phosphatidylcholine(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))	HMDB

Chemical Formula

C₄₆H₈₀NO₈P

Average Molecular Weight

806.1031

Monoisotopic Molecular Weight

805.562155053

IUPAC Name

(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=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/CCCCC

InChI Identifier

InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14-17,20-22,24-25,27,31,33,44H,6-13,18-19,23,26,28-30,32,34-43H2,1-5H3/b16-14-,17-15-,22-20-,24-21-,27-25-,33-31-/t44-/m1/s1

InChI Key

ZZSZQATYGVHNLZ-PUMLCSCDSA-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

phosphatidylcholine 38:6 (CHEBI:84563 )
Diacylglycerophosphocholines (LMGP01010943 )

Ontology

Status

Detected and 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	5.73	ALOGPS
logP	8.61	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	250.17 m³·mol⁻¹	ChemAxon
Polarizability	95.63 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	splash10-0a4i-0000000090-ca3483f6dd540baaf891	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000090-0f04b1deeba14a94356f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041210-7535b3c0ca52eb410d47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-1e78e28c2730b5262b1b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000190-f42482894aa2a9df4b6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0200498220-882e69f0546935966511	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000090-16b357af2387839179b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0011000090-3c2d12da68314bd9861c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ui6-0099000090-659059b54ab6c0df71cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000090-8b00eebc929d9a9097df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000000190-71d714a518c51ee5a089	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900369110-b70a47abc65e2e98867c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000090-6dad79f01b1173c5421f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0064004390-a2e07e22be3f1a2bfb6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-5191000000-50eb4d0b8a691e3a81ef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-489803391fb15e1d23f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000090-e0c7549473f8627cae46	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-1900041210-6a88b3160e1dd26f3b53	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Blood
Liver
Longissimus Thoracis Muscle
Milk
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected and Quantified	1 +/- 0.3 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected and Quantified	6 +/- 3 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.5 +/- 0.1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.151 +/- 0.003 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.177 +/- 0.002 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.22 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.115 +/- 0.002 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.020 +/- 0.014 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.06 +/- 0.04 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	0.6 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	21 +/- 5 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0008147

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24766809

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778979

PDB ID

Not Available

ChEBI ID

84563

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details

1. Phosphatidylserine synthase 1

General function:: Not Available
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:: PTDSS1
Uniprot ID:: Q2KHY9
Molecular weight:: 55416.0

Reactions

PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))	details

Showing metabocard for PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (BMDB0008147)

Structure for BMDB0008147 (PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

Enzymes

Reactions