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LysoPE(0:0/18:2(9Z,12Z))

PubChem CID
53480926
Structure
LysoPE(0:0/18:2(9Z,12Z))_small.png
Molecular Formula
Synonyms
  • LysoPE(0:0/18:2(9Z,12Z))
  • 2-linoleoyl-sn-glycero-3-phosphoethanolamine
  • LPE(18:2)
  • Lyso-PE(18:2)
  • LPE(0:0/18:2)
Molecular Weight
477.6 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2011-11-09
  • Modify:
    2025-02-01
Description
2-linoleoyl-sn-glycero-3-phosphoethanolamine is a 2-acyl-sn-glycero-3-phosphoethanolamine in which the acyl group is specified as linoleoyl. It has a role as a human metabolite. It is functionally related to a linoleic acid. It is a tautomer of a 2-linoleoyl-sn-glycero-3-phosphoethanolamine zwitterion.
LysoPE(0:0/18:2(9Z,12Z)) has been reported in Trypanosoma brucei with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
LysoPE(0:0/18:2(9Z,12Z)).png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Biologic Description

IUPAC Condensed
PE(0:0/18:2(9Z,12Z))
IUPAC
O2-(9Z,12Z)-octadeca-9,12-dienoyl-sn-glycero-3-phosphoethanolamine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

[(2R)-1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-hydroxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

3.1.2 InChI

InChI=1S/C23H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)31-22(20-25)21-30-32(27,28)29-19-18-24/h6-7,9-10,22,25H,2-5,8,11-21,24H2,1H3,(H,27,28)/b7-6-,10-9-/t22-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

3.1.3 InChIKey

SVRBKLJIDJHADS-USWSLJGRSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

3.1.4 SMILES

CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](CO)COP(=O)(O)OCCN
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C23H44NO7P
Computed by PubChem 2.2 (PubChem release 2024.11.20)

3.3 Other Identifiers

3.3.1 ChEBI ID

3.3.2 HMDB ID

3.3.3 Lipid Maps ID (LM_ID)

3.3.4 Metabolomics Workbench ID

3.3.5 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
477.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
1.8
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
23
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
477.28553974 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
477.28553974 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
128 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
32
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
554
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
2
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 2011.09.13)

4.2 Experimental Properties

4.2.1 Physical Description

Solid

4.2.2 Collision Cross Section

212.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

212.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]

220.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

205.95 Ų [M-H]- [CCS Type: TIMS; Method: single field calibrated]

210.86 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

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

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

4.3 Chemical Classes

4.3.1 Lipids

Lipids -> Unambiguous Lipids
Lipids -> Glycerophospholipids [GP] -> Glycerophosphoethanolamines [GP02] -> Monoacylglycerophosphoethanolamines [GP0205]

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 MS-MS

Spectra ID
Ionization Mode
Positive
Top 5 Peaks

279.23 100

280.236 22.72

Thumbnail
Thumbnail

5.1.2 LC-MS

1 of 2
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
36 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1353.6 sec
Precursor m/z
476.277
Precursor Adduct
[M-H]-
Top 5 Peaks

279.23 999

280.236 227

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 2
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1353.6 sec
Top 5 Peaks

476.2789 999

477.2816 272

953.5619 129

544.265 83

954.5646 69

Thumbnail
Thumbnail
License
CC BY-NC-SA

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Tissue Locations

All Tissues

8.1.2 Cellular Locations

  • Extracellular
  • Membrane

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

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 CCSBase Classification

12.4 LOTUS Tree

12.5 CCS Classification - Baker Lab

12.6 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    LPE(0:0/18:2)
    CCS Classification - Baker Lab
    https://tarheels.live/bakerlab/
  2. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  3. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  4. ChEBI
    2-linoleoyl-sn-glycero-3-phosphoethanolamine
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76233
  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. 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
  7. Natural Product Activity and Species Source (NPASS)
  8. MassBank Europe
    1-Hydroxy-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine (NMR)
    https://massbank.eu/MassBank/Result.jsp?inchikey=SVRBKLJIDJHADS-USWSLJGRSA-N
  9. Metabolomics Workbench
  10. Wikidata
    2-linoleoyl-sn-glycero-3-phosphoethanolamine
    https://www.wikidata.org/wiki/Q27145827
  11. PubChem
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  13. PATENTSCOPE (WIPO)
CONTENTS