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Showing metabocard for 20-Hydroxyeicosatetraenoic acid (BMDB0005998)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:19:30 UTC
Update Date2020-05-21 16:27:00 UTC
BMDB IDBMDB0005998
Secondary Accession Numbers
  • BMDB05998
Metabolite Identification
Common Name20-Hydroxyeicosatetraenoic acid
Description20-Hydroxyeicosatetraenoic acid, also known as 20-hydroxy arachidonic acid or 20-HETE, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Based on a literature review a significant number of articles have been published on 20-Hydroxyeicosatetraenoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acidChEBI
20-Hydroxy arachidonic acidChEBI
20-Hydroxyarachidonic acidChEBI
20-Hydroxyicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoateGenerator
20-Hydroxy arachidonateGenerator
20-HydroxyarachidonateGenerator
20-HydroxyicosatetraenoateGenerator
20-HydroxyeicosatetraenoateGenerator
(all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoateHMDB
(all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
20-HETEHMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateHMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acidHMDB
20-Hydroxy-5,8,11,14-eicosatetraenoateHMDB
20-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoateHMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name20-hete
CAS Registry Number79551-86-3
SMILES
OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
InChI KeyNNDIXBJHNLFJJP-DTLRTWKJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • 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
logP5.87ALOGPS
logP5.15ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.88 m³·mol⁻¹ChemAxon
Polarizability38.44 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, Positivesplash10-0007-3290000000-c19c2446fd09c9b5b114View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0g6s-8958400000-372a8a263c8ea8f0e5b0View 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, Positivesplash10-0uk9-0059000000-650b772489866747dfc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdr-2293000000-4135e55c1f638956a165View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8890000000-7333663b79a20dc52435View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-b8b23d059895b0d51482View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-2098000000-7fd830563f4a43d0b812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9040000000-ac722c9b6528d7965c21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c55e430e69fa5c79a747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1049000000-1b54cbfba7d53b2e17abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9151000000-9d68be1fa8ed76d657d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-1229000000-2c09f1a1c932d016c5e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe1-5934000000-650155a4dedf606f2045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-7900000000-c13624e44921230c2908View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005998
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023796
KNApSAcK IDNot Available
Chemspider ID4446281
KEGG Compound IDC14748
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link20-Hydroxyeicosatetraenoic acid
METLIN IDNot Available
PubChem Compound5283157
PDB IDNot Available
ChEBI ID34306
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A28
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A28
Uniprot ID:
P79102
Molecular weight:
58152.0
Reactions
Arachidonic acid + NADPH + Oxygen → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails