Bovine Metabolome Database: Showing metabocard for PC(o-16:0/20:0) (BMDB0013406)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:39:44 UTC

Update Date

2020-06-04 19:46:48 UTC

BMDB ID

BMDB0013406

Secondary Accession Numbers

BMDB13406

Metabolite Identification

Common Name

PC(o-16:0/20:0)

Description

PC(O-16:0/20:0), also known as gpcho(16:0/20:0) or gpcho(36:0), belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Thus, PC(O-16:0/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:0/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Palmityl-2-arachidonyl-sn-glycero-3-phosphocholine	ChEBI
Gpcho(16:0/20:0)	HMDB
Gpcho(36:0)	HMDB
Lecithin	HMDB
PC Ae C36:0	HMDB
PC(16:0/20:0)	HMDB
PC(36:0)	HMDB
PC(O-36:0)	HMDB
Phosphatidylcholine(16:0/20:0)	HMDB
Phosphatidylcholine(36:0)	HMDB
1-Hexadecanyl-2-eicosanoyl-sn-glycero-3-phosphocholine	HMDB
PC(o-16:0/20:0)	Lipid Annotator

Chemical Formula

C₄₄H₉₀NO₇P

Average Molecular Weight

776.1617

Monoisotopic Molecular Weight

775.645490751

IUPAC Name

(2-{[(2R)-3-(hexadecyloxy)-2-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecyloxy)-2-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C44H90NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)52-43(42-51-53(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h43H,6-42H2,1-5H3/t43-/m1/s1

InChI Key

QFZSBLJYDQLBAG-VZUYHUTRSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-alkyl,2-acylglycero-3-phosphocholines

Alternative Parents

Substituents

1-alkyl,2-acylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Glycerol ether
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-acyl-1-alkyl-sn-glycero-3-phosphocholine (CHEBI:86240 )
phosphatidylcholine O-36:0 (CHEBI:86240 )
1-alkyl,2-acylglycerophosphocholines (LMGP01020051 )

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	6.25	ALOGPS
logP	10.27	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	94.12 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	234.51 m³·mol⁻¹	ChemAxon
Polarizability	99.67 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

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

Not Available

Name	SMPDB/Pathwhiz	KEGG

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	1.6 +/- 0.4 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected and Quantified	5 +/- 2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.55 +/- 0.12 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.783 +/- 0.002 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.87 +/- 0.02 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.19 +/- 0.04 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.696 +/- 0.003 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.05 +/- 0.04 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	0.6 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.9 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0013406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029406

KNApSAcK ID

Not Available

Chemspider ID

24822862

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779297

PDB ID

Not Available

ChEBI ID

86240

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(o-16:0/20:0) (BMDB0013406)

Structure for BMDB0013406 (PC(o-16:0/20:0))