Bovine Metabolome Database: Showing metabocard for LysoPC(16:0/0:0) (BMDB0010382)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:05:30 UTC

Update Date

2020-06-04 20:05:04 UTC

BMDB ID

BMDB0010382

Secondary Accession Numbers

BMDB0062711
BMDB10382
BMDB62711

Metabolite Identification

Common Name

LysoPC(16:0/0:0)

Description

PC(16:0/0:0), also known as 16:0 lyso-PC or 1-palmitoyl-GPC, belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Thus, PC(16:0/0:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/0:0) exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
1-16:0-LysoPC	ChEBI
1-16:0-Lysophosphatidylcholine	ChEBI
1-Hexadecanoyl-2-lysophosphatidylcholine	ChEBI
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoyl-2-lysophosphatidylcholine	ChEBI
1-Palmitoyl-GPC	ChEBI
1-Palmitoyl-GPC (16:0)	ChEBI
1-Palmitoyl-phosphatidylcholine	ChEBI
1-Palmitoyl-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoylphosphatidylcholine	ChEBI
16:0 LYSO-PC	ChEBI
GPC(16:0)	ChEBI
GPC(16:0/0:0)	ChEBI
GPCho 16:0/0:0	ChEBI
GPCho(16:0/0:0)	ChEBI
LPC 16:0/0:0	ChEBI
LPC(16:0)	ChEBI
LPC(16:0/0:0)	ChEBI
LyPC(16:0)	ChEBI
LyPC(16:0/0:0)	ChEBI
LysoPC 16:0/0:0	ChEBI
LysoPC(16:0)	ChEBI
Lysophosphatidylcholine(16:0)	ChEBI
Lysophosphatidylcholine(16:0/0:0)	ChEBI
PC(16:0/0:0)	ChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
1-Palmitoyl-glycero-3-phosphocholine	HMDB
1-Palmitoyl-lysophosphatidylcholine	HMDB
LysoPC a C16:0	HMDB
1-Pam-2-lysoptdcho	HMDB
1-Hexadecanoyl-glycero-3-phosphocholine	HMDB
1-Palmitoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Palmitoylglycerol-3-phosphorylcholine	HMDB
Hydroxide inner salt(S)-isomer OF we 201	HMDB
1-O-Hexadecylpropanediol 3-phosphorylcholine	HMDB
1-Palmitoyllysophosphatidylcholine	HMDB
LYSO-PC	HMDB
Hydroxide inner salt(R)-isomer OF we 201	HMDB
Hydroxide inner salt(+-)-isomer OF we 201	HMDB
Palmitoyl lysophosphatidylcholine	HMDB
1-Hexadecanoylglycerophosphocholine	HMDB
1-Palmitoylglycerophosphocholine	HMDB
1-Hexadecanoyl-sn-glycero-3-phosphocholine	HMDB
1-Hexadecanoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Hexadecanoyllysolecithin	HMDB
1-Hexadecyl-sn-glycero-3-phosphocholine	HMDB
1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine	HMDB
1-O-Palmitoyl-sn-glycero-3-phosphocholine	HMDB
1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholine	HMDB
1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine	HMDB
1-Palmitoyl-L-alpha-lysophosphatidylcholine	HMDB
1-Palmitoyl-L-α-lysophosphatidylcholine	HMDB
1-Palmitoyl-sn-glycero-3-phosphorylcholine	HMDB
1-Palmitoyl-sn-glycerol-3-phosphatidylcholine	HMDB
1-Palmitoyl-sn-glycerol-3-phosphocholine	HMDB
1-Palmitoyllecithin	HMDB
C(16)-Lysophosphatidylcholine	HMDB
L-Palmitoyllysolecithin	HMDB
L-alpha-Lysopalmitoylphosphatidylcholine	HMDB
L-alpha-Palmitoyllysophosphatidylcholine	HMDB
L-Α-lysopalmitoylphosphatidylcholine	HMDB
L-Α-palmitoyllysophosphatidylcholine	HMDB
Lysophosphatidylcholine C16:0	HMDB
MPPC	HMDB
Palmitoyl L-alpha-lysolecithin	HMDB
Palmitoyl L-alpha-lysophosphatidylcholine	HMDB
Palmitoyl L-lysophosphatidylcholine	HMDB
Palmitoyl L-α-lysolecithin	HMDB
Palmitoyl L-α-lysophosphatidylcholine	HMDB
gamma-Palmitoyl-L-alpha-lysophosphatidylcholine	HMDB
Γ-palmitoyl-L-α-lysophosphatidylcholine	HMDB
1-Hexadecanoyl-3-glycerophosphorylcholine	HMDB
1-Palmitoyl-3-glycerylphosphorylcholine	HMDB
1-Palmitoyllysolecithin	HMDB
Palmitoyllysolecithin	HMDB
Palmitoyllysophosphatidyl choline	HMDB
LysoPC(16:0/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₄H₅₀NO₇P

Average Molecular Weight

495.6301

Monoisotopic Molecular Weight

495.332489471

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

14863-27-5

SMILES

[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1

InChI Key

ASWBNKHCZGQVJV-HSZRJFAPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysophosphatidylcholine 16:0 (CHEBI:72998 )
Monoacylglycerophosphocholines (LMGP01050018 )

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	1.83	ALOGPS
logP	1.19	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	142.27 m³·mol⁻¹	ChemAxon
Polarizability	58.03 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
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phospholipid Biosynthesis		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 but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Blood	Detected and Quantified	15-58 uM	Not Specified	Not Specified	Normal	PMID: 25157578	details
Blood	Detected and Quantified	20 +/- 4 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected and Quantified	0.7 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.1 +/- 0.02 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	1.00 +/- 0.04 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.97 +/- 0.03 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.20 +/- 0.03 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.25 +/- 0.02 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 1779072	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.018 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.019 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.02 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.14 +/- 0.02 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.14 +/- 0.02 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.3 +/- 0.2 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	0.11 +/- 0.03 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.7 +/- 0.1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0010382

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027533

KNApSAcK ID

Not Available

Chemspider ID

405287

KEGG Compound ID

C04230

BioCyc ID

CPD-8343

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

460602

PDB ID

Not Available

ChEBI ID

72998

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
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. Acyl-protein thioesterase 1

General function:: Involved in hydrolase activity
Specific function:: Acts as a acyl-protein thioesterase hydrolyzing fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS (By similarity). Has depalmitoylating activity toward KCNMA1 (By similarity). Acts as a lysophospholipase hydrolyzing various lysophospholipids including lysophosphatidylcholine (lyso-PC), lysophosphatidylethanolamine (lyso-PE), lysophosphatidylinositol (lyso-PI) and lysophosphatidylserine (lyso-PS) (By similarity). Has much higher thioesterase activity than lysophospholipase activity (By similarity). Contributes to the production of lysophosphatidic acid (LPA) during blood coagulation by recognizing and cleaving plasma phospholipids to generate lysophospholipids which in turn act as substrates for ENPP2 to produce LPA (By similarity).
Gene Name:: LYPLA1
Uniprot ID:: Q3MHR0
Molecular weight:: 24596.0

Reactions

LysoPC(16:0/0:0) → Citicoline	details

Enzyme Details

2. Phospholipase A2, membrane associated

General function:: Not Available
Specific function:: Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Thought to participate in the regulation of phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Independent of its catalytic activity, acts as a ligand for integrins. Binds to and activates integrins ITGAV:ITGB3, ITGA4:ITGB1 and ITGA5:ITGB1. Binds to a site (site 2) which is distinct from the classical ligand-binding site (site 1) and induces integrin conformational changes and enhanced ligand binding to site 1. Induces cell proliferation in an integrin-dependent manner.
Gene Name:: PLA2G2A
Uniprot ID:: Q56JZ2
Molecular weight:: 16347.0

Reactions

PC(16:0/16:0) → LysoPC(16:0/0:0)	details

Showing metabocard for LysoPC(16:0/0:0) (BMDB0010382)

Structure for BMDB0010382 (LysoPC(16:0/0:0))

Enzymes

Reactions

Reactions