Bovine Metabolome Database: Showing metabocard for PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0008715)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:27:33 UTC

Update Date

2020-05-11 18:49:39 UTC

BMDB ID

BMDB0008715

Secondary Accession Numbers

BMDB08715

Metabolite Identification

Common Name

PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Description

PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as pc(22:5(7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)) or pc(22:5(7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)), 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. PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-choline and DG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and L-serine can be converted into choline and PS(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylethanolamine biosynthesis pe(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine(22:5/22:6)	HMDB
Phosphatidylcholine(44:11)	HMDB
Lecithin	HMDB
GPCho(22:5/22:6)	HMDB
1-Docosapentaenoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine	HMDB
PC(44:11)	HMDB
PC(22:5/22:6)	HMDB
1-(7Z,10Z,13Z,16Z,19Z-Docosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine	HMDB
GPCho(44:11)	HMDB
PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	Lipid Annotator

Chemical Formula

C₅₂H₈₂NO₈P

Average Molecular Weight

880.1831

Monoisotopic Molecular Weight

879.577805117

IUPAC Name

(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(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/C\C=C/CC

InChI Identifier

InChI=1S/C52H82NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,39,41,50H,6-7,12-13,18-19,24-25,30-31,36-38,40,42-49H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-,41-39-/t50-/m1/s1

InChI Key

LIYXTHCSSCAYRI-VYKHTVRDSA-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

Not Available

Ontology

Status

Expected but not 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	5.73	ALOGPS
logP	9.47	ChemAxon
logS	-7.3	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	283.36 m³·mol⁻¹	ChemAxon
Polarizability	101.27 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000009-14c2ce6abbfe757c66ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000019-602903742dacfa745646	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0800090811-22cbf6e627928ca828a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-33ccde4ee21295e6f1bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-26e449b720fb732cc572	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1900041030-1dd78277d7d0822f6124	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-5444a903dc3d0668f571	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000000090-b5db901c6bec0e35acb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi1-0200490840-dd8ac2331edc198a932a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000090-df183a8d955b882a9013	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1009001040-3d797f62d09e0e218edc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4169000100-a979208219eb83e13d7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000009-81f97a179a89640adbfb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0003000009-eadcef00a8c8df6cc471	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0009000004-14ce7693d2f2eb21fa7c	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))		Not Available