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Record Information
Version3.6
Creation Date2009-07-25 00:03:40 UTC
Update Date2016-02-11 01:25:06 UTC
HMDB IDHMDB12598
Secondary Accession NumbersNone
Metabolite Identification
Common Name17-HETE
DescriptionElectrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)17-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid that has stereospecific effects on sodium transport in the kidney. At a concentration of 2 ¬µM the (S)-enantiomer of 17-HETE inhibits proximal tubule ATPase activity by as much as 70%, whereas the (R)-isomer is inactive.
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-17-Hydroxyeicosa-5,8,11,14-tetraenoic acidChEBI
(all-cis)-17-Hydroxy-5,8,11,14-eicosatetraenoic acidChEBI
(all-cis)-17-Hydroxy-5,8,11,14-icosatetraenoic acidChEBI
17-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-17-Hydroxyeicosa-5,8,11,14-tetraenoateGenerator
(all-cis)-17-Hydroxy-5,8,11,14-eicosatetraenoateGenerator
(all-cis)-17-Hydroxy-5,8,11,14-icosatetraenoateGenerator
17-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoateGenerator
17-Hydroxyeicosa-all-cis-5,8,11,14-tetraenoateHMDB
17-Hydroxyeicosa-all-cis-5,8,11,14-tetraenoic acidHMDB
17-HydroxyeicosatetraenateHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z)-17-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name17-hete
CAS Registry NumberNot Available
SMILES
CCCC(O)C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-16-19(21)17-14-12-10-8-6-4-3-5-7-9-11-13-15-18-20(22)23/h3,5-6,8-9,11-12,14,19,21H,2,4,7,10,13,15-18H2,1H3,(H,22,23)/b5-3-,8-6-,11-9-,14-12-
InChI KeyInChIKey=OPPIPPRXLIDJKN-JPURVOHMSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
Water Solubility0.0021 mg/mLALOGPS
logP5.79ALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.62 m3·mol-1ChemAxon
Polarizability38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000113 +/- 2.1E-5 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029141
KNApSAcK IDNot Available
Chemspider ID4946802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12598
Metagene LinkHMDB12598
METLIN IDNot Available
PubChem Compound6442740
PDB IDNot Available
ChEBI ID63995
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42