Milk Composition Database: Showing metabocard for PC(16:1(9Z)/18:0) (BMDB0008003)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:48 UTC

Update Date

2020-06-04 20:44:21 UTC

MCDB ID

BMDB0008003

Secondary Accession Numbers

BMDB08003

Metabolite Identification

Common Name

PC(16:1(9Z)/18:0)

Description

PC(16:1(9Z)/18:0), also known as gpcho(16:1/18:0) or gpcho(34:1), 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)/18:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/18:0) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/18:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/18:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/18:0); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/18:0) can be biosynthesized from CDP-choline and DG(16:1(9Z)/18:0/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/18:0) and L-serine can be converted into choline and PS(16:1(9Z)/18:0) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/18:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/18:0) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/18:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z-Hexadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(16:1/18:0)	ChEBI
GPCho(16:1n7/18:0)	ChEBI
GPCho(16:1W7/18:0)	ChEBI
PC(16:1/18:0)	ChEBI
PC(16:1n7/18:0)	ChEBI
PC(16:1W7/18:0)	ChEBI
Phosphatidylcholine(16:1/18:0)	ChEBI
Phosphatidylcholine(16:1n7/18:0)	ChEBI
Phosphatidylcholine(16:1W7/18:0)	ChEBI
1-Palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(34:1)	HMDB
Lecithin	HMDB
PC Aa C34:1	HMDB
PC(34:1)	HMDB
Phosphatidylcholine(34:1)	HMDB
PC(16:1(9Z)/18:0)	Lipid Annotator

Chemical Formula

C₄₂H₈₂NO₈P

Average Molecular Weight

760.0761

Monoisotopic Molecular Weight

759.577805117

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

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

InChI Key

LJUDFFWSOQEQKW-QCFYSATCSA-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

1,2-diacyl-sn-glycero-3-phosphocholine (CHEBI:84570 )
phosphatidylcholine 34:1 (CHEBI:84570 )
Diacylglycerophosphocholines (LMGP01011483 )

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	93.86 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, Negative	splash10-0zgr-0090000200-aabd9b01ccaebabcacc3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0090001000-c9ce3672c84c040b9bf8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kci-3090000000-cd83c0282bb21a304d0c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-b3c6e728ecd1d8ae0cd1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-da2711afa09de91feb17	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uf6-0090000400-15a15f3d3a4ccc0fbf56	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-5c2654109ac5e1768f70	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090042700-f545dd3bd7240cea0a2f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-3191300000-522cde3aa0e3a87b63ba	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kkf-0000690700-20a011228de2240a230d	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-122890d5f0b74a98dbf8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-03d1b99daac1f51a0754	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0500390200-f4006fcdb68b00a06a6a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000900-c437fa62968cd6370d11	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000000900-5d47ab6a1cc6748bc9e4	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0100390200-486972aab32bb882057b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-fc5ea85eb3704fac1e2a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-91dd06610a8a97fa32c6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900230300-85b09124d42ea56a35ca	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	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

HMDB0008003

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025194

KNApSAcK ID

Not Available

Chemspider ID

24766672

KEGG Compound ID

C00157

BioCyc ID

PHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52922448

PDB ID

Not Available

ChEBI ID

84570

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)/18:0) (BMDB0008003)

Structure for BMDB0008003 (PC(16:1(9Z)/18:0))