Bovine Metabolome Database: Showing metabocard for PC(o-16:1(9Z)/20:0) (BMDB0013414)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:39:53 UTC

Update Date

2020-06-04 20:42:47 UTC

BMDB ID

BMDB0013414

Secondary Accession Numbers

BMDB13414

Metabolite Identification

Common Name

PC(o-16:1(9Z)/20:0)

Description

PC(O-16:1(9Z)/20:0), also known as gpcho(16:1/20:0) or gpcho(36:1), 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-16:1(9Z)/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:1(9Z)/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Palmitoleyl-2-arachidonyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(16:1/20:0)	HMDB
Gpcho(16:1n7/20:0)	HMDB
Gpcho(16:1W7/20:0)	HMDB
Gpcho(36:1)	HMDB
Lecithin	HMDB
PC Ae C36:1	HMDB
PC(16:1/20:0)	HMDB
PC(16:1n7/20:0)	HMDB
PC(16:1W7/20:0)	HMDB
PC(36:1)	HMDB
PC(O-36:1)	HMDB
Phosphatidylcholine(16:1/20:0)	HMDB
Phosphatidylcholine(16:1n7/20:0)	HMDB
Phosphatidylcholine(16:1W7/20:0)	HMDB
Phosphatidylcholine(36:1)	HMDB
1-(9Z-Hexadecenyl)-2-eicosanoyl-sn-glycero-3-phosphocholine	HMDB
PC(o-16:1(9Z)/20:0)	Lipid Annotator

Chemical Formula

C₄₄H₈₈NO₇P

Average Molecular Weight

774.1458

Monoisotopic Molecular Weight

773.629840687

IUPAC Name

(2-{[(2R)-3-[(9Z)-hexadec-9-en-1-yloxy]-2-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(9Z)-hexadec-9-en-1-yloxy]-2-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COCCCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C44H88NO7P/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/h17,19,43H,6-16,18,20-42H2,1-5H3/b19-17-/t43-/m1/s1

InChI Key

NEMVGIRAGVGOLH-RPBJOJELSA-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

1-(1Z-alkenyl),2-acylglycerophosphocholines (LMGP01030107 )

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	6.21	ALOGPS
logP	9.91	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	43	ChemAxon
Refractivity	235.63 m³·mol⁻¹	ChemAxon
Polarizability	97.6 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	splash10-0019-9151321300-963c777448c7cc3e3ff3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0012-4290111000-7212c18fc45fff6d2f24	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001a-6090012100-0066d389112d876019bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-0045002900-c10de029502e9deab8d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-029i-2095006300-efb406d658e80d4a88f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01r6-6096000000-ae258fa1a14671c36871	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000900-d959e23419da5cba0687	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0021010900-ddbaa7239086c376f6d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-2019000000-486581f7cce9790d8eee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-248c1c473caf7412bbc8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000900-248c1c473caf7412bbc8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-1900340700-cb52cd3e76d511a08420	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000090-567286e8b1188ad0ea60	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000000090-567286e8b1188ad0ea60	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dk-0009201910-c5eec7c15080047a3afc	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Blood
Milk
Ruminal Fluid

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	13.4 +/- 5.1 uM	Not Specified	Not Specified	Normal	PMID: 25875852	details
Milk	Detected and Quantified	2.5 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	3.1 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	3.7 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2.59 +/- 0.04 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.04 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.005 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.02 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.06 +/- 0.05 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.06 +/- 0.05 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.017 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.011 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.015 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.057 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0013414

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029414

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

53481711

PDB ID

Not Available

ChEBI ID

89893

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-16:1(9Z)/20:0) (BMDB0013414)

Structure for BMDB0013414 (PC(o-16:1(9Z)/20:0))