Bovine Metabolome Database: Showing metabocard for PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (BMDB0008240)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:16:54 UTC

Update Date

2020-05-11 18:43:05 UTC

BMDB ID

BMDB0008240

Secondary Accession Numbers

BMDB08240

Metabolite Identification

Common Name

PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))

Description

PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)), also known as pc(18:4(6z,9z,12z,15z)/18:4(6z,9z,12z,15z)) or PC(18:4/18:4), 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(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from CDP-choline and DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) and L-serine can be converted into choline and PS(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine(36:8)	HMDB
PC(18:4/18:4)	HMDB
GPCho(18:4/18:4)	HMDB
PC(36:8)	HMDB
Phosphatidylcholine(18:4/18:4)	HMDB
1,2-Distearidonoyl-rac-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
GPCho(36:8)	HMDB
1,2-Di(6Z,9Z,12Z,15Z-octadecatetraenoyl)-rac-glycero-3-phosphocholine	HMDB
PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))	Lipid Annotator

Chemical Formula

C₄₄H₇₂NO₈P

Average Molecular Weight

774.0181

Monoisotopic Molecular Weight

773.499554797

IUPAC Name

(2-{[(2R)-2,3-bis[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]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/CCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C44H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,42H,6-7,12-13,18-19,24-25,30-41H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-/t42-/m1/s1

InChI Key

RYWHBQHFYXLTOJ-KDCFPJOHSA-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

Diacylglycerophosphocholines (LMGP01011716 )

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	4.97	ALOGPS
logP	7	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	36	ChemAxon
Refractivity	243.2 m³·mol⁻¹	ChemAxon
Polarizability	88.18 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, Negative	splash10-00di-0000000900-29976f6ae0036d58f33f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-0071030900-af8c1f64b7ad1a5f3713	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3490000000-9117d64f0d8d01b4e68b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000090-7f382382524ec62b3fb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0010000090-d6d702f0dfacf10eef2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a90-0090000090-3a7e5f95bd9bf345475d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-20436f604416a86e5e27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0600000900-c7241b809300c4bf55a6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900120300-4a90bc5adbf9f2bea780	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000900-2f46c8f353443cabfd3c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000000900-80f66c50915a042c42df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dk-0900139300-7934c95b5ff49f2b6640	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-c30ebfa3251ce2387cfd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0600000900-d13b2e4c55470f4749ea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900120300-0854812f2c5ac2fb7eb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-4e97a882d4dca5a702d2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-6ece10391313016b59fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0100190300-515d2ad092d97250068b	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))		Not Available