Showing metabocard for 18-Hydroxyarachidonic acid (BMDB0006245)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:49 UTC
Update Date2020-04-22 15:17:03 UTC
BMDB IDBMDB0006245
Secondary Accession Numbers
  • BMDB06245
Metabolite Identification
Common Name18-Hydroxyarachidonic acid
Description18-Hydroxyarachidonic acid, also known as hydroxyarachidonate or (18R)-hete, 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. 18-Hydroxyarachidonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(18R)-HETEChEBI
(5Z,8Z,11Z,14Z,18R)-18-Hydroxyicosatetraenoic acidChEBI
18(R)-Hydroxyeicosatetraenoic acidChEBI
Hydroxyarachidonic acidChEBI
(5Z,8Z,11Z,14Z,18R)-18-HydroxyicosatetraenoateGenerator
18(R)-HydroxyeicosatetraenoateGenerator
HydroxyarachidonateGenerator
18-HydroxyarachidonateGenerator
(18R)-HydroxyarachidonateHMDB
(18R)-Hydroxyarachidonic acidHMDB
18-HETEHMDB
18-HydroxyeicosatetraenoateHMDB
18-Hydroxyeicosatetraenoic acidHMDB
Omega-hydroxyarachidonic acidHMDB
W-Hydroxyarachidonic acidHMDB
18-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
18-Hydroxy-arachidonateHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name18-hydroxy-arachidonic acid
CAS Registry Number124411-81-0
SMILES
CC[C@@H](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-/t19-/m1/s1
InChI KeyPPCHNRUZQWLEMF-LFFPGIGVSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.81ALOGPS
logP5.2ChemAxon
logS-5.2ALOGPS
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
Polarizability38.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6y-7291000000-16728ad8bd8ebb944fe2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9436500000-0c21440f1fd79ba11984View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0059000000-a75bea5dd5332be1a84fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-1292000000-ef55afde193cfcd01538View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-8790000000-0eab084330a82cf88226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-710912287685513d0e07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1059000000-ad675311c547d18f97bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9030000000-a7c5a41adbeb99e30dbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-1339000000-0392a1ab82d4e70b35dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-4953000000-34622f97ba9d1fd54e9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-9600000000-7cde68db4ec7173c6177View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-777fdb814292c66079c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-3059000000-c59628baf2569d14b3c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9020000000-d11651945eb0a6c4f27dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006245
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023857
KNApSAcK IDNot Available
Chemspider ID9316866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2300206
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11141754
PDB IDNot Available
ChEBI ID91132
References
Synthesis ReferenceRomanov, Stepan G.; Ivanov, Igor V.; Groza, Nataliya V.; Kuhn, Hartmut; Myagkova, Galina I. Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids. Tetrahedron (2002), 58(42), 8483-8487.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available