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18-Hydroxy-arachidonic acid

PubChem CID
11141754
Structure
18-Hydroxy-arachidonic acid_small.png
18-Hydroxy-arachidonic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 18-hydroxy-arachidonic acid
  • 18(R)-HETE
  • 18(R)-Hydroxyeicosatetraenoic acid
  • 18R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
  • (18R)-Hydroxyarachidonate
Molecular Weight
320.5 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-10-26
  • Modify:
    2025-01-10
Description
18(R)-HETE is an 18-HETE in which the 18-hydroxy group has R-configuration. It has a role as a human xenobiotic metabolite. It is functionally related to an arachidonic acid. It is a conjugate acid of a 18(R)-HETE(1-).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
18-Hydroxy-arachidonic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-/t19-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

PPCHNRUZQWLEMF-LFFPGIGVSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CC[C@H](CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H32O3
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 Nikkaji Number

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
320.5 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
4.8
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
14
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
320.23514488 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
320.23514488 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
57.5 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
392
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
4
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 2011.04.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.3 Chemical Classes

3.3.1 Lipids

Fatty Acyls [FA] -> Eicosanoids [FA03] -> Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Human Metabolite Information

6.1.1 Cellular Locations

  • Endoplasmic reticulum
  • Extracellular
  • Membrane

7 Literature

7.1 Consolidated References

7.2 Chemical Co-Occurrences in Literature

7.3 Chemical-Gene Co-Occurrences in Literature

7.4 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 Chemical Co-Occurrences in Patents

8.3 Chemical-Disease Co-Occurrences in Patents

9 Taxonomy

10 Classification

10.1 ChEBI Ontology

10.2 LIPID MAPS Classification

10.3 EPA DSSTox Classification

10.4 MolGenie Organic Chemistry Ontology

11 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/
    (5Z,8Z,11Z,14Z,18R)-18-Hydroxy-5,8,11,14-eicosatetraenoic acid
    https://commonchemistry.cas.org/detail?cas_rn=124411-81-0
  2. EPA DSSTox
    (5Z,8Z,11Z,14Z,18R)-18-Hydroxy-5,8,11,14-eicosatetraenoic acid
    https://comptox.epa.gov/dashboard/DTXSID401179171
    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. Japan Chemical Substance Dictionary (Nikkaji)
  6. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  7. Metabolomics Workbench
  8. Natural Product Activity and Species Source (NPASS)
  9. Wikidata
  10. PubChem
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS