Bovine Metabolome Database: Showing metabocard for PC(16:1(9Z)/16:1(9Z)) (BMDB0008002)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:47 UTC

Update Date

2020-06-04 19:46:42 UTC

BMDB 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 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Intracellular membrane
Membrane

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-2c3238d389cac738936f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-36b81a67e325f0216f8c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-1bc83cd559310c83c10d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fbi-0090000400-6ac2e20ce745f6196fcc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0090001000-6bc9429c31c4de650023	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zi9-4091100000-3e65d04f14832f0c5316	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-6a6809008cae91e5f388	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090032800-826e6ae767231c2d896a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1091100000-29f09cf4791cc690aba4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-144e898f8b56e36bfc48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-647bb30a36b4a684d60b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-1fab4e82972a386b71ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-2059ce0696da48a2a005	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-e61844da3e6ca3967d64	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014k-0700291100-95f0c94c31ec2503fc30	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-76332e6fc80373c2f62d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0010000900-11669f0521fd71952691	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0xr0-0090000900-a1569473afc22b214ce4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-5f02b9487b48f138b9ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000001900-cf4a5735287140ffe940	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0100391100-cd854fc2a55818ade14b	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Blood
Liver
Longissimus Thoracis Muscle
Milk
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected and Quantified	4 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected and Quantified	3 +/- 1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	1.7 +/- 0.4 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.63 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.83 +/- 0.02 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.00 +/- 0.05 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.61 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.034 +/- 0.003 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.048 +/- 0.024 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	3 +/- 2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.5 +/- 0.1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0008002

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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.

Enzymes

Enzyme Details

1. Phosphatidylserine synthase 1

General function:: Not Available
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:: PTDSS1
Uniprot ID:: Q2KHY9
Molecular weight:: 55416.0

Reactions

PC(16:1(9Z)/16:1(9Z)) + L-Serine → Choline + PS(16:1(9Z)/16:1(9Z))	details

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

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

Enzymes

Reactions