Milk Composition Database: Showing metabocard for PC(16:1(9Z)/18:1(9Z)) (BMDB0008005)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:50 UTC

Update Date

2020-06-04 20:44:55 UTC

MCDB ID

BMDB0008005

Secondary Accession Numbers

BMDB08005

Metabolite Identification

Common Name

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

Description

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(16:1/18:1)	ChEBI
GPCho(16:1n7/18:1n9)	ChEBI
GPCho(16:1W7/18:1W9)	ChEBI
GPCho(34:2)	ChEBI
PC(16:1/18:1)	ChEBI
PC(16:1n7/18:1n9)	ChEBI
PC(16:1W7/18:1W9)	ChEBI
Phosphatidylcholine(16:1/18:1)	ChEBI
Phosphatidylcholine(16:1n7/18:1n9)	ChEBI
Phosphatidylcholine(16:1W7/18:1W9)	ChEBI
Lecithin	HMDB
PC Aa C34:2	HMDB
PC(34:2)	HMDB
Phosphatidylcholine(34:2)	HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(16:1(9Z)/18:1(9Z))	Lipid Annotator

Chemical Formula

C₄₂H₈₀NO₈P

Average Molecular Weight

758.0603

Monoisotopic Molecular Weight

757.562155053

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

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/h17,19-21,40H,6-16,18,22-39H2,1-5H3/b19-17-,21-20-/t40-/m1/s1

InChI Key

ZRCWDIULNHKQRD-RWGOWQMXSA-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:84811 )
Diacylglycerophosphocholines (LMGP01010688 )

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	5.45	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	92.23 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fi7-0000695200-48a7f33446bf9eeade79	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zgr-0090000200-050a6e388a232f6cba53	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090001000-46261eb1776c4edb01c7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kci-3090000000-5aa95502dd53f2e1a499	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-b382b9772ae071121f32	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-e509931f6dd2f1ba96fd	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900231200-c69772b3d60645bd7fa7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-4f45d46462d3badb869e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0090042700-0f3cc049f13654c0a4dc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-3191300000-8a3c20947e4487def4fc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-e3f5d1861df776418aef	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-80e8e19a84edd518095b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uf6-0090000400-79f4ee6d8252a51c2b49	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-02ab676d31620f046e54	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000900-80f99b213a3cb752bf9c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0100390200-652b5161d9c2cb1b0984	2021-09-23	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	splash10-0002-0500390200-462303c5fc844785f467	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-18	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

HMDB0008005

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025196

KNApSAcK ID

Not Available

Chemspider ID

24766674

KEGG Compound ID

C00157

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778767

PDB ID

Not Available

ChEBI ID

84811

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(16:1(9Z)/18:1(9Z)) (BMDB0008005)

Structure for BMDB0008005 (PC(16:1(9Z)/18:1(9Z)))