Livestock Metabolome Database: Showing metabocard for PC(16:1(9Z)/14:1(9Z)) (LMDB00494)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:07 UTC

Update Date

2016-07-20 20:43:29 UTC

Lmdb

LMDB00494

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(16:1(9Z)/14:1(9Z))

Description

PC(16:1(9Z)/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(16:1(9Z)/14:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, 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
1-Palmitoleoyl-2-myristoleoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(16:1n7/14:1n5)	ChEBI
GPCho(16:1W7/14:1W5)	ChEBI
PC(16:1n7/14:1n5)	ChEBI
PC(16:1W7/14:1W5)	ChEBI
Phosphatidylcholine(16:1n7/14:1n5)	ChEBI
Phosphatidylcholine(16:1W7/14:1W5)	ChEBI
Phosphatidylcholine(16:1/14:1)	HMDB
Lecithin	HMDB
GPCho(30:2)	HMDB
PC(16:1/14:1)	HMDB
Phosphatidylcholine(30:2)	HMDB
GPCho(16:1/14:1)	HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(30:2)	HMDB
PC(16:1(9Z)/14:1(9Z))	Lipid Annotator

Chemical Formula

C₃₈H₇₂NO₈P

Average Molecular Weight

701.9539

Monoisotopic Molecular Weight

701.499554797

IUPAC Name

(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C38H72NO8P/c1-6-8-10-12-14-16-18-19-21-22-24-26-28-30-37(40)44-34-36(35-46-48(42,43)45-33-32-39(3,4)5)47-38(41)31-29-27-25-23-20-17-15-13-11-9-7-2/h13,15-16,18,36H,6-12,14,17,19-35H2,1-5H3/b15-13-,18-16-/t36-/m1/s1

InChI Key

WEVWHXAKLAWWAP-KQGJYXFZSA-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

phosphatidylcholine 30:2 (CHEBI:86415 )
Diacylglycerophosphocholines (LMGP01011476 )

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	4.76	ALOGPS
logP	6.5	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	208.9 m³·mol⁻¹	ChemAxon
Polarizability	83.96 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-8190412200-69aefb2afb7f6cd3f73e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053i-4490111000-cddd9e51f52be7eab2c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9371041000-5c5fc3d4f150943129a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000200-0b0897bf9f4925390819	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0090000000-db0d065968bd886f3c90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kdr-4190000000-6f9a8cf789b018427a21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-c0264bc5a3658a84089e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000001900-f99701a4c0dc029e939b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fis-0101791100-07091dabbadf7fa8ebb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-1fd7bbea2430b811e0ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0600000900-4b1c66063a5797985307	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900412100-d5b06fcc3b23dd902711	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-015b7563f35058194e4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0030000900-fd2ae918b9bd28bf4ae8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uii-0090000400-cd9d490ca073d32c9e59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-5e86fac3277edd257bad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000001900-d689ed047e4811394499	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-0700691100-b1b962c108a0c0b79340	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-c0783fc627a546653f44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090032800-dae7a83f9fa1abd8eda8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1191000000-b81065f019c21da75732	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	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	0.009 +/- 0.002 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0007999

FooDB ID

FDB025190

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

Not Available

ChEBI ID

86415

PubChem Compound ID

52922434

Kegg Compound ID

Not Available

YMDB ID

YMDB01863

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(16:1(9Z)/14:1(9Z)) (LMDB00494)

Structure for LMDB00494 (PC(16:1(9Z)/14:1(9Z)))