Bovine Metabolome Database: Showing metabocard for PC(14:1(9Z)/20:0) (BMDB0007911)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:46:55 UTC

Update Date

2020-06-04 20:44:19 UTC

BMDB ID

BMDB0007911

Secondary Accession Numbers

BMDB07911

Metabolite Identification

Common Name

PC(14:1(9Z)/20:0)

Description

PC(14:1(9Z)/20:0), also known as gpcho(14:1/20:0) or gpcho(34:1), 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. Thus, PC(14:1(9Z)/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/20:0) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/20:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/20:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/20:0); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/20:0) can be biosynthesized from CDP-choline and DG(14:1(9Z)/20:0/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/20:0) and L-serine can be converted into choline and PS(14:1(9Z)/20:0); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/20:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/20:0) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/20:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Myristoleoyl-2-arachidonyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(14:1/20:0)	HMDB
Gpcho(14:1n5/20:0)	HMDB
Gpcho(14:1W5/20:0)	HMDB
Gpcho(34:1)	HMDB
Lecithin	HMDB
PC Aa C34:1	HMDB
PC(14:1/20:0)	HMDB
PC(14:1n5/20:0)	HMDB
PC(14:1W5/20:0)	HMDB
PC(34:1)	HMDB
Phosphatidylcholine(14:1/20:0)	HMDB
Phosphatidylcholine(14:1n5/20:0)	HMDB
Phosphatidylcholine(14:1W5/20:0)	HMDB
Phosphatidylcholine(34:1)	HMDB
1-(9Z-Tetradecenoyl)-2-eicosanoyl-sn-glycero-3-phosphocholine	HMDB
PC(14:1(9Z)/20:0)	Lipid Annotator

Chemical Formula

C₄₂H₈₂NO₈P

Average Molecular Weight

760.0761

Monoisotopic Molecular Weight

759.577805117

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13,15,40H,6-12,14,16-39H2,1-5H3/b15-13-/t40-/m1/s1

InChI Key

SJLGFZBXPQKJIH-LLVYEJTBSA-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 (LMGP01011397 )

Ontology

Status

Detected and 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	5.6	ALOGPS
logP	8.64	ChemAxon
logS	-7.6	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	41	ChemAxon
Refractivity	226.18 m³·mol⁻¹	ChemAxon
Polarizability	93.97 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	splash10-0udi-0000690700-fb9727724b61ef02ad01	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-0092000300-33116d1312a4b2ed51eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0191001000-b6f2eb7606fa766d6d3a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06vl-5293000000-c4480558368a49150bf8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-fc5ea85eb3704fac1e2a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-91dd06610a8a97fa32c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900230300-94bd04db609f7a93f865	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-5c2654109ac5e1768f70	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0062043900-aa2fd707ddaea3bab6d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-3159000000-79f5e3ff8a4bca4dcaef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-122890d5f0b74a98dbf8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-03d1b99daac1f51a0754	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0600490200-8c0b0d7255f258dddecb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-b3c6e728ecd1d8ae0cd1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0011000900-977431a0f5ef59817087	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03i6-0099000900-6d15ff6da7e535a6716e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000900-c437fa62968cd6370d11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000000900-5d47ab6a1cc6748bc9e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0101490300-9145839c0baaff67fb74	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Milk
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)		Not Available
Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)		Not Available

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
Milk	Detected and Quantified	26 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	16.1 +/- 0.5 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	17.0 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	22 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.227 +/- 0.120 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.231 +/- 0.165 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.14 +/- 0.145 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.312 +/- 0.284 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.027 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.03 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.034 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.3 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007911

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB025103

KNApSAcK ID

Not Available

Chemspider ID

24766587

KEGG Compound ID

C00157

BioCyc ID

PHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52922276

PDB ID

Not Available

ChEBI ID

88928

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for PC(14:1(9Z)/20:0) (BMDB0007911)

Structure for BMDB0007911 (PC(14:1(9Z)/20:0))