Bovine Metabolome Database: Showing metabocard for PC(14:0/18:3(9Z,12Z,15Z)) (BMDB0007876)

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 23:46:12 UTC

Update Date

2020-06-04 20:41:26 UTC

BMDB ID

BMDB0007876

Secondary Accession Numbers

BMDB07876

Metabolite Identification

Common Name

PC(14:0/18:3(9Z,12Z,15Z))

Description

PC(14:0/18:3(9Z,12Z,15Z)), also known as gpcho(14:0/18:3) or PC(32:3), 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(14:0/18:3(9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/18:3(9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/18:3(9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/18:3(9Z,12Z,15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/18:3(9Z,12Z,15Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/18:3(9Z,12Z,15Z)) can be biosynthesized from CDP-choline and DG(14:0/18:3(9Z,12Z,15Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/18:3(9Z,12Z,15Z)) and L-serine can be converted into choline and PS(14:0/18:3(9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/18:3(9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/18:3(9Z,12Z,15Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/18:3(9Z,12Z,15Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Myristoyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(14:0/18:3)	ChEBI
GPCho(14:0/18:3n3)	ChEBI
GPCho(14:0/18:3W3)	ChEBI
PC(14:0/18:3)	ChEBI
PC(14:0/18:3n3)	ChEBI
PC(14:0/18:3W3)	ChEBI
Phosphatidylcholine(14:0/18:3)	ChEBI
Phosphatidylcholine(14:0/18:3n3)	ChEBI
Phosphatidylcholine(14:0/18:3W3)	ChEBI
1-Myristoyl-2-a-linolenoyl-sn-glycero-3-phosphocholine	Generator
1-Myristoyl-2-α-linolenoyl-sn-glycero-3-phosphocholine	Generator
PC(32:3)	HMDB
Phosphatidylcholine(32:3)	HMDB
Lecithin	HMDB
GPCho(32:3)	HMDB
1-Tetradecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholine	HMDB
PC(14:0/18:3(9Z,12Z,15Z))	Lipid Annotator

Chemical Formula

C₄₀H₇₄NO₈P

Average Molecular Weight

727.9912

Monoisotopic Molecular Weight

727.515204861

IUPAC Name

trimethyl(2-{[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C40H74NO8P/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/h8,10,14,16,19-20,38H,6-7,9,11-13,15,17-18,21-37H2,1-5H3/b10-8-,16-14-,20-19-/t38-/m1/s1

InChI Key

AGQKQQAJRFTOGL-XPTMXNASSA-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 32:3 (CHEBI:86095 )
Diacylglycerophosphocholines (LMGP01010497 )

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	ALOGPS
logP	7.03	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	37	ChemAxon
Refractivity	219.21 m³·mol⁻¹	ChemAxon
Polarizability	86.99 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	splash10-03g0-7190321300-7b5634078055faa2c154	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3390010000-c2e42ded7603e4d6ed04	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-7290020000-45eaac2473697911733c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000200-ef9cd92fe636192ee5c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0190001000-99997b45607f017c2109	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-4190000000-02501e307f0fcefe3b15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-9653fbcf31b375e5170f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0600000900-bd0be299c1f1467f4b6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fsi-1900231200-a295a12c186eb3816bf8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-5b1fd914c09974aac1bc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000001900-0890e236514873d6e443	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zna-0101491100-dd6d428f36800e4bbb0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-d9526beec28bd7498c5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090032600-b60dc6ccbdfb37d6ae29	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4490000000-fabec6081aec5338bb22	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-3a99710a0b37278c42e7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0030000900-ca36c0e18e16b3a2d471	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0090000400-20ca3143f7230e16fbd0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-3775854d4a94f6be8174	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-f5b3b62817adde9c6fbb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014n-0600491100-797df8002263263f7ebf	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(14:0/18:3(9Z,12Z,15Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))		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	0.165 +/- 0.002 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.20 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.25 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.161 +/- 0.003 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.01 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.007 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.021 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.007 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.014 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.011 +/- 0.003 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007876

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

24778625

PDB ID

Not Available

ChEBI ID

86095

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(14:0/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(14:0/18:3(9Z,12Z,15Z))	details

Showing metabocard for PC(14:0/18:3(9Z,12Z,15Z)) (BMDB0007876)

Structure for BMDB0007876 (PC(14:0/18:3(9Z,12Z,15Z)))

Enzymes

Reactions