Livestock Metabolome Database: Showing metabocard for lysoPC(26:0) (LMDB00653)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:43 UTC

Update Date

2021-04-30 20:57:44 UTC

Lmdb

LMDB00653

Secondary Accession Numbers

None

Metabolite Identification

Common Name

lysoPC(26:0)

Description

LysoPC(26:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(26:0/0:0), in particular, consists of one hexacosanoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
LysoPC a C26:0	HMDB

Chemical Formula

C₃₄H₇₀NO₇P

Average Molecular Weight

635.8959

Monoisotopic Molecular Weight

635.488990111

IUPAC Name

(2-{[(2R)-3-(hexacosanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexacosanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C34H70NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-34(37)40-31-33(36)32-42-43(38,39)41-30-29-35(2,3)4/h33,36H,5-32H2,1-4H3/t33-/m1/s1

InChI Key

WSDKRPCAPHRNNZ-MGBGTMOVSA-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

Not Available

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	4.71	ALOGPS
logP	5.64	ChemAxon
logS	-7.2	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	34	ChemAxon
Refractivity	188.28 m³·mol⁻¹	ChemAxon
Polarizability	79.36 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("LysoPC(26:0/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0001009000-d4ea8c5cd386920f67ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1009000000-df670173862d3498b47e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0009000000-150908322e76777683ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000009000-8e88a23f1fe692e22d45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006t-0009007000-5ef1d3f90910a91b38da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0039003000-b8c4c95c1cfede95c62a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0000009000-74b6a743cda1b38a7134	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0900006000-1c9f342a1df47901e18d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fsi-0910004000-85040ebfb19fd447dd19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000019000-14409044759115508ada	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-0000196000-ace1709b82691ad7d077	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f92-1600971000-0b72ef78469d229c056d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000019000-1c0c90efa3ccc03b2901	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001o-0000299000-399e7dc25fa23c269196	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0300940000-7781a43575ccdb46a103	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected and Quantified	0.84 +/- 0.03 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	0.15 +/- 0.0 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1687 +/- 0.0397 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1672 +/- 0.03 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1568 +/- 0.0198 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1668 +/- 0.0278 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1669 +/- 0.0309 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1625 +/- 0.0324 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1689 +/- 0.0334 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.11 +/- 0.05 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.1563 +/- 0.0238 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1684 +/- 0.041 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1603 +/- 0.0314 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1615 +/- 0.0229 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0029205

FooDB ID

FDB031398

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

35032836

ChEBI ID

Not Available

PubChem Compound ID

131750810

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for lysoPC(26:0) (LMDB00653)

Structure for LMDB00653 (lysoPC(26:0))