Livestock Metabolome Database: Showing metabocard for PC(14:1(9Z)/14:0) (LMDB00487)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:50:56 UTC

Update Date

2016-07-20 20:43:18 UTC

Lmdb

LMDB00487

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(14:1(9Z)/14:0)

Description

PC(14:1(9Z)/14:0) 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(14:1(9Z)/14:0), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of myristic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the myristic acid moiety is derived from nutmeg and butter. 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-Myristoleoyl-2-myristoyl-sn-glycero-3-phosphocholine	HMDB
Phosphatidylcholine(28:1)	HMDB
PC(28:1)	HMDB
Phosphatidylcholine(14:1/14:0)	HMDB
Lecithin	HMDB
GPCho(14:1/14:0)	HMDB
GPCho(28:1)	HMDB
1-(9Z-Tetradecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphocholine	HMDB
PC(14:1/14:0)	HMDB
PC(14:1(9Z)/14:0)	Lipid Annotator

Chemical Formula

C₃₆H₇₀NO₈P

Average Molecular Weight

675.9167

Monoisotopic Molecular Weight

675.483904733

IUPAC Name

trimethyl(2-{[(2R)-3-[(9Z)-tetradec-9-enoyloxy]-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C36H70NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h12,14,34H,6-11,13,15-33H2,1-5H3/b14-12-/t34-/m1/s1

InChI Key

XQPYHFHTTVXZKL-XBEBLRSGSA-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 (LMGP01011381 )

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	4.46	ALOGPS
logP	5.97	ChemAxon
logS	-7.2	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	35	ChemAxon
Refractivity	198.58 m³·mol⁻¹	ChemAxon
Polarizability	81.11 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	splash10-01wk-9620553000-6d138f7e85953d4ece10	Spectrum
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	splash10-002r-9270714000-47f0054fe0edaa46537f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0910-4590301000-ebe699aa039592c32fa0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00m0-9470211000-80d4d78c93d0334a7a10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-0090018000-6387133285e85fdae2c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-1191043000-e03586a7e76be6ff03a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4291000000-8bf9668085aafe8fe155	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-23efe47e180661e62928	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0030000900-931ce8d673e04b6f55f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0090000400-ed7612e2f02e25222e13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000009000-7758c98a5dd6e0447643	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000009000-9b85e71817316dd08c1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-0800983000-f6ef0e5f0a0444f23588	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000009000-db7c90fe63745586beab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0600009000-74e9482b89e7476b0d25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-1900503000-115579516283be1e52de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000009000-724887a31238f844cc5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000009000-fcb13f9b85a7f37b5cb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-0102902000-767a404c9335cd8210aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000009000-559731194e19bf038640	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-0090308000-62495e9dcc45c3e0a3c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3394000000-040e028d94985748b842	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	0.064 +/- 0.005 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	0.25 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.27 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.21 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.28 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0007899

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

Not Available

ChEBI ID

89588

PubChem Compound ID

52922244

Kegg Compound ID

Not Available

YMDB ID

YMDB01830

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(14:1(9Z)/14:0) (LMDB00487)

Structure for LMDB00487 (PC(14:1(9Z)/14:0))