Milk Composition Database: Showing metabocard for PC(14:0/18:1(9Z)) (BMDB0007873)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:46:08 UTC

Update Date

2020-06-04 19:51:02 UTC

MCDB ID

BMDB0007873

Secondary Accession Numbers

BMDB07873

Metabolite Identification

Common Name

PC(14:0/18:1(9Z))

Description

PC(14:0/18:1(9Z)), also known as gpcho(14:0/18:1) or mopc CPD, 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(14:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/18:1(9Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(14:0/18:1(9Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/18:1(9Z)) and L-serine can be converted into choline and PS(14:0/18:1(9Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/18:1(9Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Myristoyl-2-oleoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(14:0/18:1)	ChEBI
GPCho(14:0/18:1n9)	ChEBI
GPCho(14:0/18:1W9)	ChEBI
PC(14:0/18:1)	ChEBI
PC(14:0/18:1n9)	ChEBI
PC(14:0/18:1W9)	ChEBI
Phosphatidylcholine(14:0/18:1)	ChEBI
Phosphatidylcholine(14:0/18:1n9)	ChEBI
Phosphatidylcholine(14:0/18:1W9)	ChEBI
MOPC CPD	HMDB
Lecithin	HMDB
GPCho(32:1)	HMDB
Phosphatidylcholine(32:1)	HMDB
PC(32:1)	HMDB
1-Tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(14:0/18:1(9Z))	Lipid Annotator

Chemical Formula

C₄₀H₇₈NO₈P

Average Molecular Weight

732.023

Monoisotopic Molecular Weight

731.546504989

IUPAC Name

trimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C40H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h19-20,38H,6-18,21-37H2,1-5H3/b20-19-/t38-/m1/s1

InChI Key

NXASLICYTANYBI-OQHNRNOKSA-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 32:1 (CHEBI:84808 )
Diacylglycerophosphocholines (LMGP01010492 )

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	5.26	ALOGPS
logP	7.75	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	39	ChemAxon
Refractivity	216.98 m³·mol⁻¹	ChemAxon
Polarizability	89.61 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	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0g4i-0000695200-a5492e1cf5c6631ac9fa	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0560-0090000200-c7cede786eb5ee0a9a5c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0190001000-3df5d09c81cc94e2d945	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-4190000000-1884e88116f0f9cf73ff	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-6ea32ad4dc08edccb04b	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-909418a92ec1ce82912b	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1900231200-027f616f3f576c3277a6	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-72e4b10a8d04de492e21	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-6d29a9c4f6d92278bb69	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dk-0600491100-1cf4d4ff35ffc6a2d9ff	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000900-27ef027a037d0c8fadfd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0030000900-62ce39d263a778534931	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ai-0090000400-bc1655a81dd28d38491f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-692892d313dcd3995c61	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000001900-d2164a22b9f090f20896	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0101491100-b42d46f73ce97f6a5ae8	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-8dbe5f937df1e45f5cec	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0080042900-956c0a8083ca697757fa	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1090100000-b946ca057c620f828955	2021-09-25	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	3.51 +/- 0.03 uM	PMID: 30994344	details
Detected and Quantified	4.2 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	5.2 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	3.18 +/- 0.02 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0007873

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

24778620

PDB ID

Not Available

ChEBI ID

84808

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(14:0/18:1(9Z)) (BMDB0007873)

Structure for BMDB0007873 (PC(14:0/18:1(9Z)))