Milk Composition Database: Showing metabocard for PC(15:0/16:0) (BMDB0007935)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:47:26 UTC

Update Date

2020-06-04 19:41:19 UTC

MCDB ID

BMDB0007935

Secondary Accession Numbers

BMDB07935

Metabolite Identification

Common Name

PC(15:0/16:0)

Description

PC(15:0/16:0), also known as PC(31:0) 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(15:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(15:0/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(15:0/16:0) exists in all eukaryotes, ranging from yeast to humans. PC(15:0/16:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(15:0/16:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(15:0/16:0) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(15:0/16:0) can be biosynthesized from CDP-choline and DG(15:0/16:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(15:0/16:0) and L-serine can be converted into choline and PS(15:0/16:0); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(15:0/16:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(15:0/16:0) pathway and phosphatidylethanolamine biosynthesis pe(15:0/16:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine (15:0/16:0)	ChEBI
PC(31:0)	Lipid Annotator, HMDB
Phosphatidylcholine(15:0/16:0)	Lipid Annotator, HMDB
1-pentadecanoyl-2-palmitoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
PC(15:0/16:0)	Lipid Annotator
Phosphatidylcholine(31:0)	Lipid Annotator, HMDB
GPCho(31:0)	Lipid Annotator, HMDB
1-pentadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
GPCho(15:0/16:0)	Lipid Annotator, HMDB

Chemical Formula

C₃₉H₇₈NO₈P

Average Molecular Weight

720.0123

Monoisotopic Molecular Weight

719.546504989

IUPAC Name

(2-{[(2R)-2-(hexadecanoyloxy)-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C39H78NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)48-37(36-47-49(43,44)46-34-33-40(3,4)5)35-45-38(41)31-29-27-25-23-21-19-17-15-13-11-9-7-2/h37H,6-36H2,1-5H3/t37-/m1/s1

InChI Key

LLHISNQVRRYJGL-DIPNUNPCSA-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

Diacylglycerophosphocholines (LMGP01010532 )

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	5.14	ALOGPS
logP	7.67	ChemAxon
logS	-7.5	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	211.26 m³·mol⁻¹	ChemAxon
Polarizability	89.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-f3822f55bec6bf2951f8	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0600000900-afe3351377cad58c0497	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900411200-3ec6fd348b18ed2b0d97	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000900-16254dc22394f893beec	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066u-0090012500-72a59b285ef8bcf7f96d	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a73-2191000000-dffc7830c9028f351ddb	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-4e92316dee449c997377	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000001900-62b6091747a7797adc6e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0036-0100981100-525efe9e29628e40bf22	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-8384f2d1ab787fe91aee	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000001900-ac802f4d1290cc35a61f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4k-0500391100-d74e7d7251e03e9f3065	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-28e64a2a81602cc3ba86	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0030000900-8a807a25da396ca1d381	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-14i6-0090000400-213bf1a58bce931a161a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-480d4825d0be16b2adc6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0600000900-b5c7e0247ff916201d34	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900411200-cfcc1a243fd78335568b	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	1.2 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.27 +/- 0.01 uM	PMID: 30994344	details
Detected and Quantified	1.57 +/- 0.02 uM	PMID: 30994344	details
Detected and Quantified	1.0 +/- 0.1 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0007935

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025127

KNApSAcK ID

Not Available

Chemspider ID

24766611

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778655

PDB ID

Not Available

ChEBI ID

134583

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(15:0/16:0) (BMDB0007935)

Structure for BMDB0007935 (PC(15:0/16:0))