An official website of the United States government

LysoPC(20:3(5Z,8Z,11Z))

PubChem CID
53480467
Structure
LysoPC(20:3(5Z,8Z,11Z))_small.png
Molecular Formula
Synonyms
  • LysoPC(20:3(5Z,8Z,11Z))
  • 1199257-41-4
  • 1-meadoyl-glycero-3-phosphocholine
  • 1-meadoyl-sn-glycero-3-phosphocholine
  • LysoPC(20:3(5Z,8Z,11Z)/0:0)
Molecular Weight
545.7 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2011-11-09
  • Modify:
    2025-01-18
Description
1-meadoyl-sn-glycero-3-phosphocholine is a lysophosphatidylcholine 20:3 in which the acyl group at position 1 is (5Z,8Z,11Z)-icosatrienoyl (meadoyl) and the hydroxy group at position 2 is unsubstituted. It is a lysophosphatidylcholine 20:3 and a 1-O-acyl-sn-glycero-3-phosphocholine. It is functionally related to a (5Z,8Z,11Z)-icosatrienoic acid.
LysoPC(20:3(5Z,8Z,11Z)) has been reported in Trypanosoma brucei with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
LysoPC(20:3(5Z,8Z,11Z)).png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-2-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C28H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h12-13,15-16,18-19,27,30H,5-11,14,17,20-26H2,1-4H3/b13-12-,16-15-,19-18-/t27-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

YHGXYYIGHBPDMX-BUTFDPNWSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CCCCCCCC/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C28H52NO7P
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 DSSTox Substance ID

2.3.4 HMDB ID

2.3.5 Lipid Maps ID (LM_ID)

2.3.6 Metabolomics Workbench ID

2.3.7 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
545.7 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
5.4
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
25
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
545.34814000 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
545.34814000 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
105 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
37
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
693
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Monoacylglycerophosphocholines [GP0105]

5 Chemical Vendors

6 Drug and Medication Information

6.1 Biomarker Information

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Tissue Locations

All Tissues

7.1.2 Cellular Locations

  • Extracellular
  • Membrane

8 Associated Disorders and Diseases

Disease
Pregnancy
References

PubMed: 3252730, 663967, 12833386, 2994907, 17704099, 12698507, 17061063, 16925883, 22420377, 18059417, 22494326, 23159745, 23313728, 23535240, 24704061

The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.

9 Literature

9.1 Consolidated References

9.2 Chemical Co-Occurrences in Literature

9.3 Chemical-Gene Co-Occurrences in Literature

9.4 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

11 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

12 Classification

12.1 ChEBI Ontology

12.2 LIPID MAPS Classification

12.3 EPA DSSTox Classification

12.4 LOTUS Tree

12.5 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    3,5,9-Trioxa-4-phosphanonacosa-14,17,20-trien-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (7R,14Z,17Z,20Z)-
    https://commonchemistry.cas.org/detail?cas_rn=1199257-41-4
  2. EPA DSSTox
    3,5,9-Trioxa-4-phosphanonacosa-14,17,20-trien-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (7R,14Z,17Z,20Z)-
    https://comptox.epa.gov/dashboard/DTXSID301101927
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  4. ChEBI
  5. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  6. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  7. Natural Product Activity and Species Source (NPASS)
  8. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
    LysoPC(20:3(5Z,8Z,11Z))
    https://markerdb.ca/chemicals/4271
  9. Metabolomics Workbench
  10. Wikidata
    1-meadoyl-sn-glycero-3-phosphocholine
    https://www.wikidata.org/wiki/Q27144624
  11. PubChem
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS