Milk Composition Database: Showing metabocard for LysoPC(16:0/0:0) (BMDB0010382)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-10-03 18:05:30 UTC

Update Date

2020-06-04 20:05:04 UTC

MCDB 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 )

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	1	ChemAxon
Rule of Five	Yes	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01y9-9311000000-9632c8a0304eb91f3751	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 1V, negative	splash10-001i-0010960000-db67de4509c75d7797d5	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-014i-0100190000-466a257c45e674564cc2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-014i-0300490000-fd86cfc8580fd230b8a8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-1000-1900860000-1a2c5a54bd973898558d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0zfr-2901600000-7c35aada431d2e867652	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0udi-5901100000-be073d1065c18511ab41	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 1V, positive	splash10-0002-0300900000-849ef7d9847d865ee542	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0002-0000900000-bd89b3b43b9782d3e5d0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0002-0000900000-7c8338b951da28a32df8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0002-0000900000-aa4c98d730731747150c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0002-0000900000-2d0497b2b78955e2f373	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0002-0100900000-864a738c4e243f3650a8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0002-0400900000-ce5450f53d5acc84a31e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-000t-0700900000-4ea431cd2258d012bb04	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0f8a-0900400000-584dbb5e4958e61bcab8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0f89-0900200000-2b522394881a967d30af	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0f89-0900100000-64234f354a55048175bc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0f89-0900000000-5f827a15f6679c860460	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0f89-1900000000-f09c6fb5cf772c643504	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0f89-1900000000-d5bef12c7df660f031a9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0f89-1900000000-f069c0af6b2eb74b9336	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0f89-3900000000-d43ab983a88913d21991	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0f8i-5900000000-2b2fa2819f5e2fce5fe4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0002-0000900000-0b99348189a68c7f5592	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-0002-0300900000-4249906ba39f9c0a48ea	2020-07-22	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 but not Quantified	Not Applicable	PMID: 1779072	details
Detected and Quantified	1.00 +/- 0.04 uM	PMID: 30994344	details
Detected and Quantified	0.97 +/- 0.03 uM	PMID: 30994344	details
Detected and Quantified	1.20 +/- 0.03 uM	PMID: 30994344	details
Detected and Quantified	1.25 +/- 0.02 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0010382

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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.

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

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