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

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:10 UTC

Update Date

2020-06-04 20:44:21 UTC

MCDB 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 )

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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, negative	splash10-000t-0090200800-c8db3c4042d858672ebd	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - IT 40V, negative	splash10-0006-0020000900-603012fb0ce5ff46f1ea	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, negative	splash10-0udi-0000000190-afc4cd2ac0e64fa39623	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0udl-0000000490-09171592a6955e57e163	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, negative	splash10-0f6x-0000000940-3b9edba3cc0cdfff4945	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0006-0030000910-e80b4b8f6690eea16c9d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-000x-0090000700-527aadfe756a5f2ad9a5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-053r-0090000200-e27632edecd3a83538a4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, negative	splash10-053r-0090000000-875a5d38cc2b636df4a1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 72V, negative	splash10-053r-0090000000-6bdad7ea857755dad8df	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, negative	splash10-053r-0090000000-a0160ca0a20b8ca408de	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 109V, negative	splash10-053r-0090000000-d2bc446076d9d86bbadf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, negative	splash10-053r-1090000000-a94d8052959d35d3d25e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 157V, negative	splash10-057i-5190000000-12de950663c450d5ad7f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 194V, negative	splash10-004i-9000000000-906a0ebc0dd0220ac288	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 53V, negative	splash10-0006-0000000900-0bfd0ce87b7b119d82fb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, negative	splash10-0006-0000000900-88f30608c9fd0df934c2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-0006-0000000900-fb159b53855796db7d35	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, negative	splash10-0006-0000000900-084480cec1d6930fa834	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, negative	splash10-0006-0020000900-103adeac53f876868122	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 47V, negative	splash10-000x-0090000800-a9198efdf2f4fe5ec5da	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, negative	splash10-053r-0090000200-9df170809bae304c6bc1	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-64875131a83d4fda43e6	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-dfb450caf9537c97446e	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fai-1900230300-31ec54e207b217422a2e	2017-10-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	17.0 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	22 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	26 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	16.1 +/- 0.5 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0007972

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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.

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

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