Bovine Metabolome Database: Showing metabocard for PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-16:0) (BMDB0008751)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:28:20 UTC

Update Date

2020-06-04 19:39:45 UTC

BMDB ID

BMDB0008751

Secondary Accession Numbers

BMDB08751

Metabolite Identification

Common Name

PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-16:0)

Description

PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-16:0) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-16:0), in particular, consists of one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl chain to the C-1 atom, and one 1Z-hexadecenyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Docosahexaenoyl-2-(1-enyl-palmitoyl)-sn-glycero-3-phosphocholine	HMDB
Gpcho(22:6/16:0)	HMDB
Gpcho(22:6n3/16:0)	HMDB
Gpcho(22:6W3/16:0)	HMDB
Gpcho(38:6)	HMDB
Lecithin	HMDB
PC Aa C38:6	HMDB
PC(22:6/16:0)	HMDB
PC(22:6n3/16:0)	HMDB
PC(22:6W3/16:0)	HMDB
PC(38:6)	HMDB
Phosphatidylcholine(22:6/16:0)	HMDB
Phosphatidylcholine(22:6n3/16:0)	HMDB
Phosphatidylcholine(22:6W3/16:0)	HMDB
Phosphatidylcholine(38:6)	HMDB

Chemical Formula

C₄₆H₈₀NO₇P

Average Molecular Weight

790.1037

Monoisotopic Molecular Weight

789.567240431

IUPAC Name

[2-({3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(1Z)-hexadec-1-en-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC\C=C/OC(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C46H80NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-46(48)52-43-45(44-54-55(49,50)53-42-40-47(3,4)5)51-41-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,27,29,33,35,38,41,45H,6-7,9,11-13,15,17-19,21,23,26,28,30-32,34,36-37,39-40,42-44H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,29-27-,35-33-,41-38-

InChI Key

GJRXIEGNAMFGOV-VEOGPPBOSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-acyl,2-(1z-alkenyl)-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O1-position, and one 1Z-alkenyl chain attached through an ether linkage at the O2-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl,2-(1Z-alkenyl)-glycerophosphocholines

Alternative Parents

Substituents

1-acyl,2-(1z-alkenyl)-glycerophosphocholine
Phosphocholine
Glycerol vinyl ether
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Status

Detected 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	6.17	ALOGPS
logP	9	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	94.12 Å²	ChemAxon
Rotatable Bond Count	39	ChemAxon
Refractivity	250.51 m³·mol⁻¹	ChemAxon
Polarizability	94.19 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	splash10-01p9-9033212500-7f77203207c77cc6d7fb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03l9-5294102200-90569d451e12f13a86b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ei-6092021000-354d7433e92aad6c0260	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0550-0029000400-b88c699c2f6259eacd82	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0029000100-3b2a07d4233737dfde17	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-5069200000-b23eb8e901b23a4b5929	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2100001900-3c31070db76513caaf15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2900000300-c740a26f733ae5286534	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0911000000-8a836c13dc306bf56d69	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-ccee64249dd340e638d0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0002000900-53ae7978af80d8809620	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-6479100000-e3318c3608c870526811	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Blood

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

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
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24888604	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 20647382	details