Bovine Metabolome Database: Showing metabocard for PC(16:1(9Z)/18:2(9Z,12Z)) (BMDB0008006)

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 23:48:52 UTC

Update Date

2020-06-04 20:41:43 UTC

BMDB ID

BMDB0008006

Secondary Accession Numbers

BMDB08006

Metabolite Identification

Common Name

PC(16:1(9Z)/18:2(9Z,12Z))

Description

PC(16:1(9Z)/18:2(9Z,12Z)), also known as gpcho(16:1/18:2) or lecithin, 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(16:1(9Z)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/18:2(9Z,12Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(16:1(9Z)/18:2(9Z,12Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/18:2(9Z,12Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z-Hexadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine	ChEBI
GPCho(16:1/18:2)	ChEBI
GPCho(16:1n7/18:2n6)	ChEBI
GPCho(16:1W7/18:2W6)	ChEBI
PC(16:1/18:2)	ChEBI
PC(16:1n7/18:2n6)	ChEBI
PC(16:1W7/18:2W6)	ChEBI
Phosphatidylcholine(16:1/18:2)	ChEBI
Phosphatidylcholine(16:1n7/18:2n6)	ChEBI
Phosphatidylcholine(16:1W7/18:2W6)	ChEBI
1-Palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
Phosphatidylcholine(34:3)	HMDB
GPCho(34:3)	HMDB
PC(34:3)	HMDB
1-Palmitoleoyl-2-linoleoyl-GPC	HMDB
1-Palmitoleoyl-2-linoleoyl-sn-glycero-phosphatidylcholine	HMDB
GPC(16:1(9Z)/18:2(9Z,12Z))	HMDB
GPC(16:1/18:2)	HMDB
GPC(16:1n7/18:2n6)	HMDB
GPC(16:1W7/18:2W6)	HMDB
GPC(34:3)	HMDB
GPCho(16:1(9Z)/18:2(9Z,12Z))	HMDB
Phosphatidylcholine(16:1(9Z)/18:2(9Z,12Z))	HMDB
PC(16:1(9Z)/18:2(9Z,12Z))	Lipid Annotator

Chemical Formula

C₄₂H₇₈NO₈P

Average Molecular Weight

756.0444

Monoisotopic Molecular Weight

755.546504989

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16-17,19-21,40H,6-13,15,18,22-39H2,1-5H3/b16-14-,19-17-,21-20-/t40-/m1/s1

InChI Key

QJWDAOSZZYVBJZ-KXESGEQTSA-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 34:3 (CHEBI:84567 )
Diacylglycerophosphocholines (LMGP01010690 )

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	5.4	ALOGPS
logP	7.92	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	39	ChemAxon
Refractivity	228.42 m³·mol⁻¹	ChemAxon
Polarizability	90.98 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-7190220300-02f77b9d7f06b00e64ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3290010000-b35293c5a0086f069aad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-7192011000-b3f68d6530ffd3425451	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000200-5219f29db4a36bf01049	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090001000-4168da6e9d0734ea2617	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kdr-3090000000-059acbdcc7d901a56a0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-178043a88be6f491ac6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000000900-13496904f0fd4fc1981e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0500390200-73cfb30e90e00128bced	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-7438791c506b384c79b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-a1440059050d26e01e58	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ui6-0090000400-3c3945b904a6d97aaac1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-3cb602c3acfc6a68ce4b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090032700-61a55a1320c27551cfe0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2190100000-d4fd4103d9f9161a262a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-7d3df73fbaa9dffe7d9e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-785a8f601a463a4cb653	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-1900231200-73b1a9cb2ee55f5678ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-b5946ddd213bca84cd6e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000900-8697b097e89237a32dd7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0100390200-880ba2e4e20016ba2d70	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Milk
Placenta
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))		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	0.84 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.98 +/- 0.04 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.3 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.74 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.019 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	0.006 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.026 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.009 +/- 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	0.06 +/- 0.003 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.038 +/- 0.021 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0008006

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

24778768

PDB ID

Not Available

ChEBI ID

84567

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(16:1(9Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(16:1(9Z)/18:2(9Z,12Z))	details

Showing metabocard for PC(16:1(9Z)/18:2(9Z,12Z)) (BMDB0008006)

Structure for BMDB0008006 (PC(16:1(9Z)/18:2(9Z,12Z)))

Enzymes

Reactions