Milk Composition Database: Showing metabocard for PC(16:0/18:2(9Z,12Z)) (BMDB0007973)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:12 UTC

Update Date

2020-06-04 20:44:54 UTC

MCDB ID

BMDB0007973

Secondary Accession Numbers

BMDB07973

Metabolite Identification

Common Name

PC(16:0/18:2(9Z,12Z))

Description

PC(16:0/18:2(9Z,12Z)), also known as GPC(16:0/18:2) or gpcho 16:0/18:2(9Z,12Z), 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(16:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:0/18:2(9Z,12Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(16:0/18:2(9Z,12Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:2(9Z,12Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Palmitoyl-2-linoleoyl-GPC	ChEBI
1-Palmitoyl-2-linoleoyl-GPC (16:0/18:2)	ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholine	ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycerophosphatidylcholine	ChEBI
1-Palmitoyl-2-linoleoylphosphatidylcholine	ChEBI
GPC(16:0/18:2)	ChEBI
GPCho 16:0/18:2(9Z,12Z)	ChEBI
GPCho(16:0/18:2(9Z,12Z))	ChEBI
GPCho(16:0/18:2)	ChEBI
GPCho(16:0/18:2omega6)	ChEBI
Lecithin	ChEBI
PC 16:0/18:2(9Z,12Z)	ChEBI
PC(16:0/18:2)	ChEBI
PC(16:0/18:2omega6)	ChEBI
PC(34:2)	ChEBI
Phosphatidylcholine 16:0/18:2(9Z,12Z)	ChEBI
Phosphatidylcholine(16:0/18:2(9Z,12Z))	ChEBI
Phosphatidylcholine(16:0/18:2)	ChEBI
Phosphatidylcholine(16:0/18:2omega6)	ChEBI
Gpcho(34:2)	HMDB
Phosphatidylcholine(34:2)	HMDB
2-Linoleoyl-1-palmitoyl-sn-phosphatidylcholine	HMDB
Palmitoyl-linoleoatephosphatidylcholine	HMDB
PLPC	HMDB
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine	HMDB
1-Palmitoyl-2-linoleoyl-3-phosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyl-3-sn-glycerophosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyllecithin	HMDB
GPC(16:0/18:2(9Z,12Z))	HMDB
GPC(16:0/18:2n6)	HMDB
GPC(16:0/18:2W6)	HMDB
GPC(34:2)	HMDB
GPCho(16:0/18:2n6)	HMDB
GPCho(16:0/18:2W6)	HMDB
L-alpha-1-Palmitoyl-2-linoleoylphosphatidylcholine	HMDB
L-Α-1-palmitoyl-2-linoleoylphosphatidylcholine	HMDB
PC(16:0/18:2n6)	HMDB
PC(16:0/18:2W6)	HMDB
Phosphatidylcholine(16:0/18:2n6)	HMDB
Phosphatidylcholine(16:0/18:2W6)	HMDB
PC(16:0/18:2(9Z,12Z))	Lipid Annotator, ChEBI

Chemical Formula

C₄₂H₈₀NO₈P

Average Molecular Weight

758.0603

Monoisotopic Molecular Weight

757.562155053

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

6931-84-6

SMILES

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

InChI Identifier

InChI=1S/C42H80NO8P/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/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1

InChI Key

JLPULHDHAOZNQI-ZTIMHPMXSA-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 34:2 (CHEBI:73002 )
Diacylglycerophosphocholines (LMGP01010594 )

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	5.48	ALOGPS
logP	8.28	ChemAxon
logS	-7.5	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	227.3 m³·mol⁻¹	ChemAxon
Polarizability	92.66 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0udl-0000000490-b7304b809294dbb2ea74	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, negative	splash10-0006-0000000940-6acae25b185d1a864052	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0006-0030000910-537e946aca08f069e72b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-002f-0090000700-ecca901df00a9bff124c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-004i-0090000200-fa34aef5028ed4787c4c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, negative	splash10-004i-0090000000-d9440bc0e6a9f6cdaf65	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 72V, negative	splash10-004i-0090000000-a5231d807bde53ae849a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 90V, negative	splash10-056r-0090000000-23038428933dc1fcc66d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 109V, negative	splash10-056r-0090000000-ccce70356f7c7b18cbbf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, negative	splash10-056r-1090000000-32df8fc00b6e170aa02a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 157V, negative	splash10-004i-7190000000-811ed3f1fe9d51baf806	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 193V, negative	splash10-004i-9000000000-4bd8d3812cfdbafe42c7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 53V, negative	splash10-0006-0000000900-aed1ee56f1886685cef5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, negative	splash10-0006-0000000900-f70fecaaa4c193d6952d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-0006-0000000900-40ddf52a50eed646c5c3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, negative	splash10-0006-0000000900-79413b6bfab2c2699ebb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 40V, negative	splash10-0006-0020000900-30d6507c6252bceda2ab	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 46V, negative	splash10-002f-0090000800-e35e5d8e6ef65358f1d7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, negative	splash10-004i-0090000200-d82c61ca09093ce2f75a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 59V, negative	splash10-004i-0090000000-a788f61f6153073cc513	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, negative	splash10-056r-0090000000-5242b45696e3aa936e70	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 89V, negative	splash10-056r-0090000000-23038428933dc1fcc66d	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-73b8731f1bdde398585f	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-37c5a628d36a084e1386	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-1900231200-522c9f77a95c208b08bc	2017-10-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	7.7 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	9.5 +/- 0.5 uM	PMID: 30994344	details
Detected and Quantified	6.9 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	11.0 +/- 0.4 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0007973

DrugBank ID

DB02306

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030253

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5287971

PDB ID

CPL

ChEBI ID

73002

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(16:0/18:2(9Z,12Z)) (BMDB0007973)

Structure for BMDB0007973 (PC(16:0/18:2(9Z,12Z)))