Milk Composition Database: Showing metabocard for PC(14:1(9Z)/20:1(11Z)) (BMDB0007912)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:46:56 UTC

Update Date

2020-06-04 20:44:53 UTC

MCDB ID

BMDB0007912

Secondary Accession Numbers

BMDB07912

Metabolite Identification

Common Name

PC(14:1(9Z)/20:1(11Z))

Description

PC(14:1(9Z)/20:1(11Z)), also known as gpcho(14:1/20:1) or gpcho(34:2), 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(14:1(9Z)/20:1(11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/20:1(11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/20:1(11Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/20:1(11Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/20:1(11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/20:1(11Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/20:1(11Z)) can be biosynthesized from CDP-choline and DG(14:1(9Z)/20:1(11Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/20:1(11Z)) and L-serine can be converted into choline and PS(14:1(9Z)/20:1(11Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/20:1(11Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/20:1(11Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/20:1(11Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Myristoleoyl-2-eicosenoyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(14:1/20:1)	HMDB
Gpcho(14:1n5/20:1n9)	HMDB
Gpcho(14:1W5/20:1W9)	HMDB
Gpcho(34:2)	HMDB
Lecithin	HMDB
PC Aa C34:2	HMDB
PC(14:1/20:1)	HMDB
PC(14:1n5/20:1n9)	HMDB
PC(14:1W5/20:1W9)	HMDB
PC(34:2)	HMDB
Phosphatidylcholine(14:1/20:1)	HMDB
Phosphatidylcholine(14:1n5/20:1n9)	HMDB
Phosphatidylcholine(14:1W5/20:1W9)	HMDB
Phosphatidylcholine(34:2)	HMDB
1-(9Z-Tetradecenoyl)-2-(11-eicosenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(14:1(9Z)/20:1(11Z))	Lipid Annotator

Chemical Formula

C₄₂H₈₀NO₈P

Average Molecular Weight

758.0603

Monoisotopic Molecular Weight

757.562155053

IUPAC Name

(2-{[(2R)-2-[(11Z)-icos-11-enoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13,15,19-20,40H,6-12,14,16-18,21-39H2,1-5H3/b15-13-,20-19-/t40-/m1/s1

InChI Key

OLUKQTJCNPHKRC-LYJZGNKWSA-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 (LMGP01011398 )

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	5.46	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	92.34 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000695200-ff0f7bf1e6c89bac40d0	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0092000300-7b4c3014feb0a9a42cfd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0191001000-90412ddf6b750ca83f66	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-5293000000-859173051fb53c09f7ae	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-02ab676d31620f046e54	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000900-80f99b213a3cb752bf9c	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0101490300-19f77c48c4b2b0c87b12	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-4f45d46462d3badb869e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0072043900-5cc27fd5b0e0b9bae9cd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-3269000000-b49da80c1fcb72876dfb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-b382b9772ae071121f32	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-e509931f6dd2f1ba96fd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900231200-324a1b22eaee1311f985	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-e3f5d1861df776418aef	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0011000900-9dc79b8dad4f0c585798	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a96-0099000900-16b3f97973b70ad7fe54	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-8ecd56b42b9f6b271e5d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-ab98c2d6a7f897263cd4	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0600490200-09aafb71510e1313bdb5	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-21	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

HMDB0007912

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025104

KNApSAcK ID

Not Available

Chemspider ID

24766588

KEGG Compound ID

C00157

BioCyc ID

PHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52922278

PDB ID

Not Available

ChEBI ID

88919

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(14:1(9Z)/20:1(11Z)) (BMDB0007912)

Structure for BMDB0007912 (PC(14:1(9Z)/20:1(11Z)))