Bovine Metabolome Database: Showing metabocard for PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (BMDB0008714)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:27:31 UTC

Update Date

2020-05-11 18:49:39 UTC

BMDB ID

BMDB0008714

Secondary Accession Numbers

BMDB08714

Metabolite Identification

Common Name

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

Description

PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)), also known as pc(22:5(7z,10z,13z,16z,19z)/22:5(7z,10z,13z,16z,19z)) or pc(22:5(7z,10z,13z,16z,19z)/22:5(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)/22:5(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)/22:5(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)/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-choline and DG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) and L-serine can be converted into choline and PS(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(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)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylethanolamine biosynthesis pe(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine(22:5/22:5)	HMDB
GPCho(44:10)	HMDB
Phosphatidylcholine(44:10)	HMDB
Lecithin	HMDB
PC(22:5/22:5)	HMDB
PC(44:10)	HMDB
GPCho(22:5/22:5)	HMDB
1,2-Di(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-rac-glycero-3-phosphocholine	HMDB
1,2-Didocosapentaenoyl-rac-glycero-3-phosphocholine	HMDB
PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))	Lipid Annotator

Chemical Formula

C₅₂H₈₄NO₈P

Average Molecular Weight

882.199

Monoisotopic Molecular Weight

881.593455181

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C52H84NO8P/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/h8-11,14-17,20-23,26-29,32-35,50H,6-7,12-13,18-19,24-25,30-31,36-49H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-/t50-/m1/s1

InChI Key

XAFPNZQFSGKDDB-WRSGPNQTSA-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	5.79	ALOGPS
logP	9.83	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	42	ChemAxon
Refractivity	282.24 m³·mol⁻¹	ChemAxon
Polarizability	103.12 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-0000000090-d68969c61947563878e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-175145361f93f686fca9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900021030-332171e5d0352b7739e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-1e383c1959112c6940cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000000090-70f258c1c7c8de632cda	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0200240940-e28c824c82ff71c0de57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-26ee6a1180a1a9b7fba4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-94f8dfad6de73ae3283c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900021030-bcefaee276584e8e6af1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000090-117d61d3d1a2c4c66043	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0009003080-ecd6df9f5af31aaf4be9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3149000000-e14d7503b488970260d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000009-babd0b6becf20d2df65d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0001000009-9af6b281157edc23ec9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0190-0009000009-7baaf77407fd7fddc153	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000009-74927739644039f49907	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000019-dc1c1b6e5dd2d1d310a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dk-0900040911-cdc3557a882915cb5695	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)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available