An official website of the United States government

1'-[1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho]-sn-glycerol

PubChem CID
118702998
Structure
1'-[1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho]-sn-glycerol_small.png
Molecular Formula
Synonyms
  • 1'-[1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho]-sn-glycerol
  • CL(1'-[20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)],3'-[18:1(9Z)/18:1(9Z)])
  • LMGP12011209
  • CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))
Molecular Weight
1478.0 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2016-02-25
  • Modify:
    2025-01-11

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1'-[1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho]-sn-glycerol.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-3-[[(2S)-3-[[(2R)-2,3-bis[[(Z)-octadec-9-enoyl]oxy]propoxy]-hydroxyphosphoryl]oxy-2-hydroxypropoxy]-hydroxyphosphoryl]oxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C83H146O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h21,24-25,28,33-37,39-42,44,52,56,77-79,84H,5-20,22-23,26-27,29-32,38,43,45-51,53-55,57-76H2,1-4H3,(H,89,90)(H,91,92)/b25-21-,28-24-,37-33-,39-34-,40-35-,41-36-,44-42-,56-52-/t77-,78+,79+/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

VPOAWXGKVXETKW-RITAIXFSSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](COP(=O)(O)OC[C@@H](COC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)O)OC(=O)CCCCCCC/C=C\CCCCCCCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C83H146O17P2
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 HMDB ID

2.3.2 Lipid Maps ID (LM_ID)

2.3.3 Metabolomics Workbench ID

2.3.4 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
1478.0 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
25.1
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
17
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
80
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
1477.00352718 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
1477.00352718 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
237 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
102
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
2310
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
3
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
8
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 2015.09.10)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Glycerophospholipids [GP] -> Glycerophosphoglycerophosphoglycerols [GP12] -> Diacylglycerophosphoglycerophosphodiradylglycerols [GP1201]

5 Pharmacology and Biochemistry

5.1 Human Metabolite Information

5.1.1 Cellular Locations

Membrane

5.1.2 Metabolite Pathways

5.2 Biochemical Reactions

6 Literature

6.1 Consolidated References

7 Interactions and Pathways

7.1 Pathways

8 Classification

8.1 LIPID MAPS Classification

8.2 MolGenie Organic Chemistry Ontology

9 Information Sources

  1. 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
    CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))
    http://www.hmdb.ca/metabolites/HMDB0058490
  2. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  3. Metabolomics Workbench
    CL(1'-[20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)],3'-[18:1(9Z)/18:1(9Z)])
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=73486
  4. Wikidata
    [(2R)-3-[[(2S)-3-[[(2R)-2,3-bis[[(Z)-octadec-9-enoyl]oxy]propoxy]-hydroxyphosphoryl]oxy-2-hydroxypropoxy]-hydroxyphosphoryl]oxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
    https://www.wikidata.org/wiki/Q76831604
  5. PubChem
  6. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS