Livestock Metabolome Database: Showing metabocard for PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (LMDB00521)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:42 UTC

Update Date

2021-04-30 20:57:49 UTC

Lmdb

LMDB00521

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)

Description

PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of stearic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
GPCho(22:6/18:0)	Lipid Annotator, HMDB
GPCho(40:6)	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
Phosphatidylcholine(40:6)	Lipid Annotator, HMDB
PC(40:6)	Lipid Annotator, HMDB
1-docosahexaenoyl-2-stearoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
Phosphatidylcholine(22:6/18:0)	Lipid Annotator, HMDB
PC(22:6/18:0)	Lipid Annotator, HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)	Lipid Annotator

Chemical Formula

C₄₈H₈₄NO₈P

Average Molecular Weight

834.1562

Monoisotopic Molecular Weight

833.593455181

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(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/C48H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,28,30,34,36,46H,6-7,9,11-13,15,17-19,21,23,26-27,29,31-33,35,37-45H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,30-28-,36-34-/t46-/m1/s1

InChI Key

AHWXJDWBIIDPKS-TZUVPVEASA-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 (LMGP01012107 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	6.21	ALOGPS
logP	9.5	ChemAxon
logS	-7.5	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	259.37 m³·mol⁻¹	ChemAxon
Polarizability	99.23 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000090-002c799c60fc4d73f51d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0011000090-95996a0eceb154950c1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ai-0099000090-16f8aee1b2f1f1764802	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000090-984ea4236848a8ef68fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0045005390-9e4594672bb9bc84614e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4297400000-e17d33f202be66e44525	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-a40775102b4d4f815a48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-d8c58c6fa3297db5857e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900041120-721fc981a3b2eb2de080	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-25d8a8b10dfd14fc7816	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000190-70c32db1d1532dee3550	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-0900179110-38584900c0b472da0b79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000090-69be100d9c131d43eb56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000190-4beaa04d4cbeaad3182c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0200498220-374f7165d7cf8482e296	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000090-34edac6f4ace79854def	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000090-1e3aed1deea007ebddb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900041120-e55f8251a338f6ee78ee	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	1.81 +/- 0.451 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	11.7906 +/- 5.6684 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.5759 +/- 5.2611 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.63 +/- 3.23 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	10.868 +/- 4.0812 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.9962 +/- 4.3543 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	13.9 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	10.9 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	17 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	14.3261 +/- 5.3209 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.159 +/- 6.1592 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.416 +/- 5.1008 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.9724 +/- 6.4534 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.7993 +/- 3.1967 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.9395 +/- 4.9916 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.7334 +/- 7.9095 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.1181 +/- 4.2773 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0008727

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

24767388

ChEBI ID

Not Available

PubChem Compound ID

52923691

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (LMDB00521)

Structure for LMDB00521 (PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0))