Milk Composition Database: Showing metabocard for PC(16:1(9Z)/16:1(9Z)) (BMDB0008002)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:47 UTC

Update Date

2020-06-04 19:46:42 UTC

MCDB ID

BMDB0008002

Secondary Accession Numbers

BMDB08002

Metabolite Identification

Common Name

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

Description

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Di-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1,2-Dipalmitoleoyl-sn-glycero-3-phosphorylcholine	ChEBI
Dipalmitoleoyl-L-alpha-glycerophosphorylcholine	ChEBI
GPCho(16:1/16:1)	ChEBI
GPCho(16:1n7/16:1n7)	ChEBI
GPCho(16:1W7/16:1W7)	ChEBI
GPCho(32:2)	ChEBI
L-Dipalmitoleoyllecithin	ChEBI
PC 16:1(9Z)/16:1(9Z)	ChEBI
PC(16:1/16:1)	ChEBI
PC(16:1n7/16:1n7)	ChEBI
PC(16:1W7/16:1W7)	ChEBI
PC(32:2)	ChEBI
Phosphatidylcholine(16:1/16:1)	ChEBI
Phosphatidylcholine(16:1n7/16:1n7)	ChEBI
Phosphatidylcholine(16:1W7/16:1W7)	ChEBI
Phosphatidylcholine(32:2)	ChEBI
Dipalmitoleoyl-L-a-glycerophosphorylcholine	Generator
Dipalmitoleoyl-L-α-glycerophosphorylcholine	Generator
1,2-Dipalmitoleoyl-rac-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
PC Aa C32:2	HMDB
1,2-Di(9Z-hexadecenoyl)-rac-glycero-3-phosphocholine	HMDB
PC(16:1(9Z)/16:1(9Z))	Lipid Annotator

Chemical Formula

C₄₀H₇₆NO₈P

Average Molecular Weight

730.0071

Monoisotopic Molecular Weight

729.530854925

IUPAC Name

(2-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h16-19,38H,6-15,20-37H2,1-5H3/b18-16-,19-17-/t38-/m1/s1

InChI Key

GPWHCUUIQMGELX-VHQDNGOZSA-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 32:2 (CHEBI:83717 )
Diacylglycerophosphocholines (LMGP01010684 )

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	5.12	ALOGPS
logP	7.39	ChemAxon
logS	-7.4	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	38	ChemAxon
Refractivity	218.1 m³·mol⁻¹	ChemAxon
Polarizability	87.95 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	splash10-001i-0000000900-2c3238d389cac738936f	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-36b81a67e325f0216f8c	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-1bc83cd559310c83c10d	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fbi-0090000400-6ac2e20ce745f6196fcc	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0090001000-6bc9429c31c4de650023	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zi9-4091100000-3e65d04f14832f0c5316	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-6a6809008cae91e5f388	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090032800-826e6ae767231c2d896a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1091100000-29f09cf4791cc690aba4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-144e898f8b56e36bfc48	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-647bb30a36b4a684d60b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-1fab4e82972a386b71ce	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-2059ce0696da48a2a005	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-e61844da3e6ca3967d64	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014k-0700291100-95f0c94c31ec2503fc30	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-76332e6fc80373c2f62d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0010000900-11669f0521fd71952691	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0xr0-0090000900-a1569473afc22b214ce4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-5f02b9487b48f138b9ff	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000001900-cf4a5735287140ffe940	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0100391100-cd854fc2a55818ade14b	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.63 +/- 0.01 uM	PMID: 30994344	details
Detected and Quantified	0.83 +/- 0.02 uM	PMID: 30994344	details
Detected and Quantified	1.00 +/- 0.05 uM	PMID: 30994344	details
Detected and Quantified	0.61 +/- 0.01 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0008002

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025193

KNApSAcK ID

Not Available

Chemspider ID

24766671

KEGG Compound ID

C00157

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778764

PDB ID

Not Available

ChEBI ID

83717

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)/16:1(9Z)) (BMDB0008002)

Structure for BMDB0008002 (PC(16:1(9Z)/16:1(9Z)))