Bovine Metabolome Database: Showing metabocard for PC(14:0/18:2(9Z,12Z)) (BMDB0007874)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:46:10 UTC

Update Date

2020-06-04 19:46:41 UTC

BMDB ID

BMDB0007874

Secondary Accession Numbers

BMDB07874

Metabolite Identification

Common Name

PC(14:0/18:2(9Z,12Z))

Description

PC(14:0/18:2(9Z,12Z)), also known as gpcho(14:0/18:2) or PC(32:2), 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(14:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/18:2(9Z,12Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(14:0/18:2(9Z,12Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(14:0/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/18:2(9Z,12Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Myristoyl-2-linoleoyl-sn-glycero-3-phosphocholine	ChEBI
1-Tetradecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine	ChEBI
GPCho(14:0/18:2)	ChEBI
GPCho(14:0/18:2n6)	ChEBI
GPCho(14:0/18:2W6)	ChEBI
PC(14:0/18:2)	ChEBI
PC(14:0/18:2n6)	ChEBI
PC(14:0/18:2W6)	ChEBI
Phosphatidylcholine(14:0/18:2)	ChEBI
Phosphatidylcholine(14:0/18:2n6)	ChEBI
Phosphatidylcholine(14:0/18:2W6)	ChEBI
PC(32:2)	HMDB
Lecithin	HMDB
GPCho(32:2)	HMDB
Phosphatidylcholine(32:2)	HMDB
1-Myristoyl-2-linoleoyl-GPC	HMDB
1-Myristoyl-2-linoleoyl-sn-glycero-phosphatidylcholine	HMDB
GPC(14:0/18:2(9Z,12Z))	HMDB
GPC(14:0/18:2)	HMDB
GPC(14:0/18:2n6)	HMDB
GPC(14:0/18:2W6)	HMDB
GPC(32:2)	HMDB
GPCho(14:0/18:2(9Z,12Z))	HMDB
Phosphatidylcholine(14:0/18:2(9Z,12Z))	HMDB
PC(14:0/18:2(9Z,12Z))	Lipid Annotator

Chemical Formula

C₄₀H₇₆NO₈P

Average Molecular Weight

730.0071

Monoisotopic Molecular Weight

729.530854925

IUPAC Name

trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium

Traditional Name

trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h14,16,19-20,38H,6-13,15,17-18,21-37H2,1-5H3/b16-14-,20-19-/t38-/m1/s1

InChI Key

IWXJKHSPEQSQMD-GMGFYYQASA-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 32:2 (CHEBI:86094 )
Diacylglycerophosphocholines (LMGP01010496 )

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	5.13	ALOGPS
logP	7.39	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	218.1 m³·mol⁻¹	ChemAxon
Polarizability	88.4 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	splash10-03ei-7190221300-a5a6efe992d3c6f1e3d4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3390010000-1314bc9c8cd7a105f02e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-7290011000-c18b0610220e0b7b4769	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000200-d2f40ed6abb56bd3c7eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0190001000-8dc4a8bffe30ccd22187	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4190000000-e9f383a24479f58c44d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-6a6809008cae91e5f388	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090011300-3d1f8257d77c7e082ba2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-3291000000-6e5954d897a914d4b9b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-76332e6fc80373c2f62d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0030000900-58c7d430d67a279f4405	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0090000400-442c60c0f88343bcec71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-5f02b9487b48f138b9ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000001900-cf4a5735287140ffe940	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi1-0101491100-5169741670a31907bd3a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-144e898f8b56e36bfc48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-647bb30a36b4a684d60b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1900231200-69af3f1942482eb3ba02	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-2059ce0696da48a2a005	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-e61844da3e6ca3967d64	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0600491100-15b6cd11ed5b5ce12681	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Blood
Liver
Longissimus Thoracis Muscle
Milk
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))		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
Blood	Detected and Quantified	4 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected and Quantified	3 +/- 1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	1.7 +/- 0.4 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.63 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.83 +/- 0.02 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.00 +/- 0.05 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.61 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.048 +/- 0.024 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	0.034 +/- 0.003 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semimembranosus Muscle	Detected and Quantified	3 +/- 2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.5 +/- 0.1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007874

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778624

PDB ID

Not Available

ChEBI ID

86094

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.

Enzymes

Enzyme Details

1. Phosphatidylserine synthase 1

General function:: Not Available
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:: PTDSS1
Uniprot ID:: Q2KHY9
Molecular weight:: 55416.0

Reactions

PC(14:0/18:2(9Z,12Z)) + L-Serine → Choline + PS(14:0/18:2(9Z,12Z))	details

Showing metabocard for PC(14:0/18:2(9Z,12Z)) (BMDB0007874)

Structure for BMDB0007874 (PC(14:0/18:2(9Z,12Z)))

Enzymes

Reactions