Bovine Metabolome Database: Showing metabocard for PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (BMDB0008378)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:20:03 UTC

Update Date

2020-05-11 18:45:00 UTC

BMDB ID

BMDB0008378

Secondary Accession Numbers

BMDB08378

Metabolite Identification

Common Name

PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))

Description

PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)), also known as pc(20:3(5z,8z,11z)/20:4(5z,8z,11z,14z)) or pc(20:3(5z,8z,11z)/20:4(5z,8z,11z,14z)), 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(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) and L-serine can be converted into choline and PS(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine(40:7)	HMDB
GPCho(40:7)	HMDB
Lecithin	HMDB
1-Meadoyl-2-arachidonoyl-sn-glycero-3-phosphocholine	HMDB
GPCho(20:3/20:4)	HMDB
PC(40:7)	HMDB
Phosphatidylcholine(20:3/20:4)	HMDB
1-(5Z,8Z,11Z-Eicosatrienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(20:3/20:4)	HMDB
PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))	Lipid Annotator

Chemical Formula

C₄₈H₈₂NO₈P

Average Molecular Weight

832.1403

Monoisotopic Molecular Weight

831.577805117

IUPAC Name

(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C48H82NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,20-23,26-29,32-35,46H,6-14,16,18-19,24-25,30-31,36-45H2,1-5H3/b17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-/t46-/m1/s1

InChI Key

WDSGLVUDWOEVDV-NALRNXKASA-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	5.88	ALOGPS
logP	9.14	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	41	ChemAxon
Refractivity	260.49 m³·mol⁻¹	ChemAxon
Polarizability	99.4 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	splash10-001i-0000000090-79f227f2d9029f28e7e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-924f091d218719cd1b75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-1900041120-624e31d81224b37818b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-9ba117d1c0de1c2e67a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-d0b4cd4d5b1d3c3b81bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041120-6f2cc2910f346ed87c57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-28e9f69759c65edf3511	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000000190-f4871623ad0b081e303c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pe9-0200498220-7d1cc9f75975bf6469f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000090-b0b8959ba582c76807b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0003000090-145c027cd96a7ab6046a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-15mi-0009000040-d200e358aeda9f1dc1a2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000090-620340c637035e66e687	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000190-3bb76294110b3cbe4d52	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-0900369110-12dbc3dd17ee5ee203c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000090-9663725765fd23c75bff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0540-0029003370-b1124500d2569b392712	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5149100000-f2be4403070e26a343d0	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))		Not Available