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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:42:19 UTC
Update Date2021-09-14 15:43:40 UTC
HMDB IDHMDB0062302
Secondary Accession Numbers
  • HMDB62302
Metabolite Identification
Common Name18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Description18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule. It is classified as a member of the hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic.
Structure
Data?1563866293
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-18-Hydroxy-5,8,11,14-eicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-18-Hydroxyeicosa-5,8,11,14-tetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-18-Hydroxyicosa-5,8,11,14-tetraenoic acidChEBI
(Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-eicosatetraenoic acidChEBI
(Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-icosatetraenoic acidChEBI
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-18-Hydroxy-5,8,11,14-eicosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-18-Hydroxyeicosa-5,8,11,14-tetraenoateGenerator
(5Z,8Z,11Z,14Z)-18-Hydroxyicosa-5,8,11,14-tetraenoateGenerator
(Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-eicosatetraenoateGenerator
(Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-icosatetraenoateGenerator
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoateGenerator
18-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
18-Hydroxyeicosatetraenoic acidHMDB
18-Hydroxyarachidonic acidHMDB
18-HETEHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.473
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z)-18-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name18-hete
CAS Registry Number133268-58-3
SMILES
CCC(O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
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-
InChI KeyPPCHNRUZQWLEMF-XBOCNYGYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.002 g/lALOGPS
LogP5.81ALOGPS
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(5.81) g/LALOGPS
logP10(5.2) g/LChemAxon
logS10(-5.2) g/LALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.62 m³·mol⁻¹ChemAxon
Polarizability37.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.38431661259
DarkChem[M-H]-191.0631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TMS,#1CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2712.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TMS,#2CCC(O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2568.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,2TMS,#1CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2605.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TBDMS,#1CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2955.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TBDMS,#2CCC(O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2818.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,2TBDMS,#1CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3086.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f97-7291000000-33d0a3568a9892f048132017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9436500000-0c21440f1fd79ba119842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Positive-QTOFsplash10-0udi-0059000000-a75bea5dd5332be1a84f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Positive-QTOFsplash10-0udr-1292000000-a91689bb888d83d363db2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Positive-QTOFsplash10-1000-8790000000-0eab084330a82cf882262017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Negative-QTOFsplash10-014i-0019000000-710912287685513d0e072017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Negative-QTOFsplash10-0uxr-1059000000-ad675311c547d18f97bb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Negative-QTOFsplash10-0a4l-9030000000-a7c5a41adbeb99e30dbc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Negative-QTOFsplash10-014i-0009000000-777fdb814292c66079c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Negative-QTOFsplash10-0gb9-3059000000-c59628baf2569d14b3c32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Negative-QTOFsplash10-0a4l-9020000000-d11651945eb0a6c4f27d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Positive-QTOFsplash10-0uk9-1339000000-0392a1ab82d4e70b35db2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Positive-QTOFsplash10-0fri-4953000000-34622f97ba9d1fd54e9b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Positive-QTOFsplash10-015c-9600000000-7cde68db4ec7173c61772021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6442778
PDB IDNot Available
ChEBI ID63579
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.