Bovine Metabolome Database: Showing metabocard for PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (BMDB0008212)

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 17:16:13 UTC

Update Date

2020-06-04 20:05:09 UTC

BMDB ID

BMDB0008212

Secondary Accession Numbers

BMDB08212

Metabolite Identification

Common Name

PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))

Description

PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)), also known as gpcho(18:3/20:3) or gpcho(38:6), 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(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) and L-serine can be converted into choline and PS(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-a-linolenoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
GPCho(18:3/20:3)	Lipid Annotator, HMDB
PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))	Lipid Annotator
GPCho(38:6)	Lipid Annotator, HMDB
Phosphatidylcholine(38:6)	Lipid Annotator, HMDB
PC(18:3/20:3)	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
Phosphatidylcholine(18:3/20:3)	Lipid Annotator, HMDB
1-(9Z,12Z,15Z-octadeatrienoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
PC(38:6)	Lipid Annotator, HMDB

Chemical Formula

C₄₆H₈₀NO₈P

Average Molecular Weight

806.1031

Monoisotopic Molecular Weight

805.562155053

IUPAC Name

(2-{[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCC\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/h9,11,14-17,20-22,24-25,27,44H,6-8,10,12-13,18-19,23,26,28-43H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,24-21-,27-25-/t44-/m1/s1

InChI Key

WZLXKZRHVGVNTE-NYMMKBANSA-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 (LMGP01011691 )

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	5.7	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	splash10-000i-9082041220-271596ccc1a41524ae27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4192021100-fbe9a1e3aeebc711c743	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9085003100-59958df93e111ec0cbef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pdi-0092000030-025bfb889f30b1ae0d5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0090000100-5fb6f044924d0f77d474	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-4092000000-e16c2cdfa81dc2bd52a7	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	splash10-001i-1900041210-090a85973689c73b02b8	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-a90ad92fa7f31896965f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a96-0099000090-e6fbd96b53f6230754d9	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	splash10-0zfr-0074005390-2b5f1a747e4c2ea8a64d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7295500000-06c73c1fb0423eaa3881	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-bed1e8ca6df5d95ed732	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	splash10-0002-0900369110-4fcca559e523ce31c68b	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

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

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(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
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

HMDB0008212

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24766874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52922861

PDB ID

Not Available

ChEBI ID

Not Available

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(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))	details

Showing metabocard for PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (BMDB0008212)

Structure for BMDB0008212 (PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)))

Enzymes

Reactions