Bovine Metabolome Database: Showing metabocard for PC(O-16:0/18:2(9Z,12Z)) (BMDB0011151)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:13:41 UTC

Update Date

2020-06-04 20:40:45 UTC

BMDB ID

BMDB0011151

Secondary Accession Numbers

BMDB11151

Metabolite Identification

Common Name

PC(O-16:0/18:2(9Z,12Z))

Description

PC(O-16:0/18:2(9Z,12Z)), also known as PC ae C34:2 or PC(O-34:2), 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-16:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(O-16:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexadecyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine	ChEBI
2-(9Z,12Z-Octadecadienoyl)-1-hexadecyl-sn-glycero-3-phosphocholine	HMDB
PC Ae C34:2	HMDB
PC(16:0E/18:2(9Z,12Z))	HMDB
PC(O-34:2)	HMDB
[(2R)-3-Hexadecoxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-trimethylazaniumylethyl phosphate	HMDB

Chemical Formula

C₄₂H₈₂NO₇P

Average Molecular Weight

744.0767

Monoisotopic Molecular Weight

743.582890495

IUPAC Name

(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

88542-95-4

SMILES

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

InChI Identifier

InChI=1S/C42H82NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)50-41(40-49-51(45,46)48-38-36-43(3,4)5)39-47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,41H,6-13,15,17-19,21,23-40H2,1-5H3/b16-14-,22-20-/t41-/m1/s1

InChI Key

IQACMFWAGALEAQ-WESJWMGVSA-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:86231 )
phosphatidylcholine O-34:2 (CHEBI:86231 )
1-alkyl,2-acylglycerophosphocholines (LMGP01020039 )

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	5.86	ALOGPS
logP	8.66	ChemAxon
logS	-7.5	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	40	ChemAxon
Refractivity	227.55 m³·mol⁻¹	ChemAxon
Polarizability	92.68 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	splash10-01q0-9170321300-dbd7856d52c0aa092c20	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g0-3290111000-2345c437d6514d4c63c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-7090022000-2630e93789ae7b753477	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0090003700-619264aad469d6299fc5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004u-1091006100-9abf3093eddcb9a13e76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-4091000000-70d3982de65c2c7f9291	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-23872d2e94db2d9fdf31	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-0060012900-27c3aa121cb366946f75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4091200000-64e10c7f3565c8d5c670	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-190e542fe7b67b8c2014	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000000900-190e542fe7b67b8c2014	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-0061201900-3adf33f5c1cb71fb8333	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-414ec66860f431bd7276	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-414ec66860f431bd7276	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-1900341600-1c67b05fa14757dd6ff5	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

Blood
Milk
Ruminal Fluid

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 20647382	details
Milk	Detected and Quantified	0.416 +/- 0.002 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.541 +/- 0.004 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.66 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.40 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.004 +/- 0.003 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.004 +/- 0.002 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	0.018 +/- 0.011 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.018 +/- 0.011 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.004 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.004 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.008 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

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

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

6443157

PDB ID

Not Available

ChEBI ID

Not Available

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-16:0/18:2(9Z,12Z)) (BMDB0011151)

Structure for BMDB0011151 (PC(O-16:0/18:2(9Z,12Z)))