Bovine Metabolome Database: Showing metabocard for PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) (BMDB0007989)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:31 UTC

Update Date

2020-06-04 19:35:16 UTC

BMDB ID

BMDB0007989

Secondary Accession Numbers

BMDB07989

Metabolite Identification

Common Name

PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))

Description

PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)), also known as pc(16:0/22:5(4z,7z,10z,13z,16z)) or pc(16:0/22:5(4z,7z,10z,13z,16z)), 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(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/22:5(4Z,7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-choline and DG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) and L-serine can be converted into choline and PS(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Palmitoyl-2-docosapentaenoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(16:0/22:5n6)	ChEBI
GPCho(16:0/22:5W6)	ChEBI
PC(16:0/22:5)	ChEBI
Phosphatidylcholine(16:0/22:5n6)	ChEBI
Phosphatidylcholine(16:0/22:5W6)	ChEBI
PC(38:5)	HMDB
Phosphatidylcholine(38:5)	HMDB
GPCho(38:5)	HMDB
Lecithin	HMDB
GPCho(16:0/22:5)	HMDB
Phosphatidylcholine(16:0/22:5)	HMDB
1-Hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine	HMDB
1-Palmitoyl-2-osbondoyl-sn-glycero-3-phosphocholine	HMDB
PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))	Lipid Annotator

Chemical Formula

C₄₆H₈₂NO₈P

Average Molecular Weight

808.1189

Monoisotopic Molecular Weight

807.577805117

IUPAC Name

(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C46H82NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16,20-21,23-24,27,29,33,35,44H,6-13,15,17-19,22,25-26,28,30-32,34,36-43H2,1-5H3/b16-14-,21-20-,24-23-,29-27-,35-33-/t44-/m1/s1

InChI Key

MWXAIAMSOXOQJK-JIXVGTEKSA-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 38:5 (CHEBI:84795 )
Diacylglycerophosphocholines (LMGP01010645 )

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	5.99	ALOGPS
logP	8.97	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	41	ChemAxon
Refractivity	249.05 m³·mol⁻¹	ChemAxon
Polarizability	96.96 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	splash10-0a4i-0000000090-48c6ffcc5a302570c7be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000090-5674e41146fd29b1e9c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-1900221210-b85e9b79a4c5e0ac8d0c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0093000030-59925738f38d022bdf4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0091000100-f2187ef7cdfed894a1e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvr-5095000000-a61df26a5edcfa2f883f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-176beaa64b72d3c99c1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000090-c545a38bbe96927ef016	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900221210-827a8888cdbb7155b900	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-f63d7860e3264d19dfbc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000190-9706f6071dcd0d9077fb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0200669220-8aaf2a722f3a50f2192a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000090-09c683f4e3532312072e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0046004390-7f6fc686afd42535bfe3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4292000000-9b98e0043dd9edf35a3c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-982a5de1a95b33baa9fb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000190-700b9d4c4e1a88e5359e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900179110-878494e4a1e5722fad9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000090-2ed1617616dcbd8a27a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0011000090-1548f80abffb0d893333	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a96-0099000090-200925bcdc93927a64d2	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))		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
Ruminal Fluid	Detected and Quantified	0.015 +/- 0.007 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007989

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778735

PDB ID

Not Available

ChEBI ID

84795

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) (BMDB0007989)

Structure for BMDB0007989 (PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)))