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1-O-Octadecyl-SN-glycero-3-phosphocholine

PubChem CID
2733532
Structure
1-O-Octadecyl-SN-glycero-3-phosphocholine_small.png
Molecular Formula
Synonyms
  • 1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE
  • 74430-89-0
  • 1-Octadecyl-sn-glycero-3-phosphocholine
  • PC(O-18:0/0:0)
  • LysoPC(O-18:0)
Molecular Weight
509.7 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Parent Compound
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
1-O-octadecyl-sn-glycero-3-phosphocholine is a 1-alkyl-sn-glycero-3-phosphocholine in which the alkyl group is specified as octadecyl It is an organic molecular entity and a 1-alkyl-sn-glycero-3-phosphocholine.
1-O-Octadecyl-SN-glycero-3-phosphocholine has been reported in Marphysa sanguinea with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1-O-Octadecyl-SN-glycero-3-phosphocholine.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-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

XKBJVQHMEXMFDZ-AREMUKBSSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CCCCCCCCCCCCCCCCCCOC[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

C26H56NO6P
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DSSTox Substance ID

2.3.5 HMDB ID

2.3.6 Lipid Maps ID (LM_ID)

2.3.7 Metabolomics Workbench ID

2.3.8 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
509.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
7
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
26
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
509.38452550 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
509.38452550 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
88.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
34
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
478
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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
0
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

3.2.2 Collision Cross Section

238.2 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

238.4 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

240.1 Ų [M+CH3COO]- [CCS Type: TIMS; Method: single field calibrated]

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Monoalkylglycerophosphocholines [GP0106]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

NIST Number
1118012
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
510.3918
Total Peaks
11
m/z Top Peak
184.1
m/z 2nd Highest
492.4
m/z 3rd Highest
433.2
Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Extracellular
  • Membrane

8.2 Biochemical Reactions

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

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

11 Biological Test Results

11.1 BioAssay Results

12 Taxonomy

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

13 Classification

13.1 ChEBI Ontology

13.2 LIPID MAPS Classification

13.3 NORMAN Suspect List Exchange Classification

13.4 CCSBase Classification

13.5 EPA DSSTox Classification

13.6 LOTUS Tree

13.7 MolGenie Organic Chemistry Ontology

14 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/
    1-O-Octadecyl-sn-glycero-3-phosphocholine
    https://commonchemistry.cas.org/detail?cas_rn=74430-89-0
  2. EPA DSSTox
    1-O-Octadecyl-sn-glycero-3-phosphocholine
    https://comptox.epa.gov/dashboard/DTXSID30274414
    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. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  5. ChEBI
    1-O-octadecyl-sn-glycero-3-phosphocholine
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75216
  6. 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/
    1-O-Octadecyl-SN-glycero-3-phosphocholine
    https://www.wikidata.org/wiki/Q27105036
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
  9. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  10. Metabolomics Workbench
  11. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  12. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  13. Wikidata
    1-O-octadecyl-sn-glycero-3-phosphocholine
    https://www.wikidata.org/wiki/Q27105036
  14. PubChem
  15. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  17. PATENTSCOPE (WIPO)
CONTENTS