Livestock Metabolome Database: Showing metabocard for PC(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z)) (LMDB00519)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:40 UTC

Update Date

2021-04-30 20:57:45 UTC

Lmdb

LMDB00519

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z))

Description

PC(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z)) 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(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z)), in particular, consists of one chain of docosapentaenoic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The docosapentaenoic acid moiety is derived from animal fats and brain, while the myristoleic acid moiety is derived from milk fats. 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
Phosphatidylcholine(36:6)	Lipid Annotator, HMDB
PC(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z))	Lipid Annotator
GPCho(36:6)	Lipid Annotator, HMDB
GPCho(22:5/14:1)	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
Phosphatidylcholine(22:5/14:1)	Lipid Annotator, HMDB
1-osbondoyl-2-myristoleoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
PC(36:6)	Lipid Annotator, HMDB
1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
PC(22:5/14:1)	Lipid Annotator, HMDB
1-Docosapentaenoyl-2-myristoleoyl-sn-glycero-3-phosphocholine	HMDB
gpcho(22:5n6/14:1n5)	HMDB
gpcho(22:5W6/14:1W5)	HMDB
PC Aa C36:6	HMDB
PC(22:5n6/14:1n5)	HMDB
PC(22:5W6/14:1W5)	HMDB
Phosphatidylcholine(22:5n6/14:1n5)	HMDB
Phosphatidylcholine(22:5W6/14:1W5)	HMDB

Chemical Formula

C₄₄H₇₆NO₈P

Average Molecular Weight

778.0499

Monoisotopic Molecular Weight

777.530854925

IUPAC Name

(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-26-17-15-13-11-9-7-2/h13-16,19-20,22-23,25,27,30,32,42H,6-12,17-18,21,24,26,28-29,31,33-41H2,1-5H3/b15-13-,16-14-,20-19-,23-22-,27-25-,32-30-/t42-/m1/s1

InChI Key

XGLZBINKZRQAPD-OTMYLMJASA-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 (LMGP01012233 )

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	5.43	ALOGPS
logP	7.72	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	38	ChemAxon
Refractivity	240.97 m³·mol⁻¹	ChemAxon
Polarizability	90.68 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, Positive	splash10-01ri-9154151300-cfea3ee09369fd95fb31	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08gr-5695130100-5fd719b8f0c04c15e3c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-9346021100-5b1a8c5bcb847e8712f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0049000300-37bc1e23bf4016c48ff7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0029001000-12c67a7029edd2c3f691	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-7297100000-785a81ffd6e2b6ba2ecf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-5a1f7e5d648203ccaa08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0051030900-f37f3145b5c6da5f4bc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1129000000-22826ec77f2ecccca9dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000090-e97180150486da753e49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000190-cd910875d8659ad53678	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0900449110-2cfb44f3de81e4422695	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000090-87e491c712a61c58fe72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0011000090-7f9dda42b2a9366e09f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0099000090-9cc2aa4c0558ae928a0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-e158c1e70dedba30b57e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0600000900-259bce635b325b3b4835	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900230300-d2c342e9454bd44eaf38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-41c33084af9f783c847d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-dd151cc7bd543b751825	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0202649400-935bfeae2aa67aadbb2a	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	0.017 +/- 0.007 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	0.652 +/- 0.1985 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.5873 +/- 0.1295 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.608 +/- 0.1558 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.577 +/- 0.256 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.18 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.18 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.11 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.22 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.6461 +/- 0.1695 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.5622 +/- 0.177 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.591 +/- 0.2005 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.6625 +/- 0.1986 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.6653 +/- 0.3255 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.6375 +/- 0.2177 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.604 +/- 0.2868 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.636 +/- 0.2256 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.34 +/- 0.15 uM	Not Available	Ovine	Candidate serum m...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0008657

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

24767318

ChEBI ID

Not Available

PubChem Compound ID

53479277

Kegg Compound ID

Not Available

YMDB ID

YMDB02191

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z)) (LMDB00519)

Structure for LMDB00519 (PC(22:5(4Z,7Z,10Z,13Z,16Z)/14:1(9Z)))