Bovine Metabolome Database: Showing metabocard for PC(16:0/18:1(9Z)) (BMDB0007972)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:10 UTC

Update Date

2020-06-04 20:44:21 UTC

BMDB ID

BMDB0007972

Secondary Accession Numbers

BMDB07972

Metabolite Identification

Common Name

PC(16:0/18:1(9Z))

Description

PC(16:0/18:1(9Z)), also known as PC(16:0/18:1) or 1-POPC, 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(16:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:1(9Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(16:0/18:1(9Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:1(9Z)) and L-serine can be converted into choline and PS(16:0/18:1(9Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:1(9Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-16:0-2-18:1-Phosphatidylcholine	ChEBI
1-Hexadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoyl-2-oleoyl-GPC	ChEBI
1-Palmitoyl-2-oleoyl-GPC (16:0/18:1)	ChEBI
1-Palmitoyl-2-oleoyl-lecithin	ChEBI
1-Palmitoyl-2-oleoylphosphatidylcholine	ChEBI
1-Palmotoyl-2-oleoylglycero-3-phosphocholine	ChEBI
1-POPC	ChEBI
16:0-18:1-PC	ChEBI
GPC(16:0/18:1)	ChEBI
GPCho(16:0/18:1)	ChEBI
GPCho(16:0/18:1omega9)	ChEBI
GPCho(34:1)	ChEBI
Lecithin	ChEBI
Palmitoyloleoylphosphatidylcholine	ChEBI
PC(16:0/18:1)	ChEBI
PC(16:0/18:1omega9)	ChEBI
PC(34:1)	ChEBI
Phosphatidylcholine(16:0/18:1)	ChEBI
Phosphatidylcholine(16:0/18:1omega9)	ChEBI
Phosphatidylcholine(34:1)	ChEBI
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylcholine	MeSH
alpha-Phosphatidylcholine-beta-oleoyl-gamma-palmitoyl	MeSH
1-Palmitoyl-2-oleoyl-phosphatidylcholine	MeSH
1-Palmitoyl-2-oleoylphosphatidylcholine, (R)-(Z)-isomer	MeSH
POPC Lipid	MeSH
beta-Oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholine	MeSH
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine	Lipid Annotator, MeSH, HMDB
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
PC(16:0/18:1(9Z))	Lipid Annotator, ChEBI
1-Palmitoyl-2-oleoyl-3-sn-phosphatidylcholine	HMDB
1-Palmitoyl-2-oleoyl-L-alpha-lecithin	HMDB
1-Palmitoyl-2-oleoyl-L-alpha-phosphatidylcholine	HMDB
1-Palmitoyl-2-oleoyl-L-α-lecithin	HMDB
1-Palmitoyl-2-oleoyl-L-α-phosphatidylcholine	HMDB
1-Palmitoyl-2-oleoyl-sn-3-phosphocholine	HMDB
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphorylcholine	HMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphatidylcholine	HMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphocholine	HMDB
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphatidylcholine	HMDB
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine	HMDB
1-Palmitoyl-2-oleoyl-sn-glyceryl-3-phosphorylcholine	HMDB
1-Palmitoyl-2-oleoyllecithin	HMDB
1-Palmitoyl-2-oleyl-3-sn-phosphatidylcholine	HMDB
2-Oleo-1-palmitin phosphate choline ester	HMDB
2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine	HMDB
2-Oleoyl-1-palmitoyllecithin	HMDB
GPC(16:0/18:1(9Z))	HMDB
GPC(16:0/18:1n9)	HMDB
GPC(16:0/18:1w9)	HMDB
GPC(34:1)	HMDB
GPCho(16:0/18:1(9Z))	HMDB
GPCho(16:0/18:1n9)	HMDB
GPCho(16:0/18:1w9)	HMDB
L-1-Palmitoyl-2-oleoylphosphatidylcholine	HMDB
L-Palmitoyloleoylphosphatidylcholine	HMDB
L-alpha-1-Palmitoyl-2-oleoylphosphatidylcholine	HMDB
L-α-1-Palmitoyl-2-oleoylphosphatidylcholine	HMDB
PC(16:0/18:1n9)	HMDB
PC(16:0/18:1w9)	HMDB
POPC	HMDB
Phosphatidylcholine(16:0/18:1(9Z))	HMDB
Phosphatidylcholine(16:0/18:1n9)	HMDB
Phosphatidylcholine(16:0/18:1w9)	HMDB
β-Oleoyl-γ-palmitoyl-L-α-phosphatidylcholine	HMDB

Chemical Formula

C₄₂H₈₂NO₈P

Average Molecular Weight

760.0761

Monoisotopic Molecular Weight

759.577805117

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

6753-55-5

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1

InChI Key

WTJKGGKOPKCXLL-VYOBOKEXSA-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 34:1 (CHEBI:73001 )
Diacylglycerophosphocholines (LMGP01010005 )

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	5.59	ALOGPS
logP	8.64	ChemAxon
logS	-7.6	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	41	ChemAxon
Refractivity	226.18 m³·mol⁻¹	ChemAxon
Polarizability	94 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

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Milk
Placenta
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))		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
Milk	Detected and Quantified	26 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	16.1 +/- 0.5 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	17.0 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	22 +/- 1 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	0.227 +/- 0.120 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.231 +/- 0.165 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.14 +/- 0.145 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.312 +/- 0.284 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.027 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.03 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.034 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.3 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007972

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030200

KNApSAcK ID

Not Available

Chemspider ID

4593686

KEGG Compound ID

Not Available

BioCyc ID

CPD-8157

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497103

PDB ID

Not Available

ChEBI ID

73001

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. Phosphatidylethanolamine N-methyltransferase

General function:: Involved in phosphatidylethanolamine N-methyltransferas
Specific function:: Catalyzes the three sequential steps of the methylation pathway of phosphatidylcholine biosynthesis, the SAM-dependent methylation of phosphatidylethanolamine (PE) to phosphatidylmonomethylethanolamine (PMME), PMME to phosphatidyldimethylethanolamine (PDME), and PDME to phosphatidylcholine (PC).
Gene Name:: PEMT
Uniprot ID:: Q7YRH6
Molecular weight:: 22018.0

Reactions

S-Adenosylmethionine + PE-NMe2(16:0/18:1(9Z)) → S-Adenosylhomocysteine + PC(16:0/18:1(9Z))	details

Enzyme Details

2. 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(16:0/18:1(9Z)) + L-Serine → Choline + PS(16:0/18:1(9Z))	details

Showing metabocard for PC(16:0/18:1(9Z)) (BMDB0007972)

Structure for BMDB0007972 (PC(16:0/18:1(9Z)))

Enzymes

Reactions

Reactions