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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-14 00:39:19 UTC
Update Date2020-02-26 21:25:12 UTC
HMDB IDHMDB0004693
Secondary Accession Numbers
  • HMDB04693
Metabolite Identification
Common Name11H-14,15-EETA
Description11H-14,15-EETA is an epoxyeicosatrienoic acid. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593 , 12361727 , 1650001 ).
Structure
Data?1582752312
Synonyms
ValueSource
11-Hydroxy-14,15-eetaKegg
11-Hydroxy-14,15-epoxyeicosatrienoic acidKegg
(5Z,8Z,12E)-14,15-Epoxy-11-hydroxyeicosa-5,8,12-trienoic acidKegg
(5Z,8Z,12E)-14,15-Epoxy-11-hydroxyicosa-5,8,12-trienoic acidKegg
11-Hydroxy-14,15-epoxyeicosatrienoateGenerator
(5Z,8Z,12E)-14,15-Epoxy-11-hydroxyeicosa-5,8,12-trienoateGenerator
(5Z,8Z,12E)-14,15-Epoxy-11-hydroxyicosa-5,8,12-trienoateGenerator
11-Hydroxy-14,15-epoxy-5Z,8Z,12E-eicosatrienoateHMDB
11-Hydroxy-14,15-epoxy-5Z,8Z,12E-eicosatrienoic acidHMDB
14(15)-EpETrEHMDB
14,15-Ep-11-hetreHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,12E)-11-hydroxy-13-(3-pentyloxiran-2-yl)trideca-5,8,12-trienoic acid
Traditional Name11-Hydroxy-14,15-EETA
CAS Registry Number219535-29-2
SMILES
CCCCCC1OC1\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-9-13-18-19(24-18)16-15-17(21)12-10-7-5-4-6-8-11-14-20(22)23/h4,6-7,10,15-19,21H,2-3,5,8-9,11-14H2,1H3,(H,22,23)/b6-4-,10-7-,16-15+
InChI KeyWLMZMBKVRPUYIG-LTCHCNGXSA-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
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.007 g/LALOGPS
logP5.47ALOGPS
logP4.57ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.72 m³·mol⁻¹ChemAxon
Polarizability39.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9873000000-ed6582b4b7518cdd5f09Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05y3-9123200000-0e1ff165c7f7d8c2c8a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-e10492fb509cb4033c3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fzi-9343000000-eca676d54a3e92ece753Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9430000000-363d17471028c56afad7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-781410c7d10fb2618b30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-3469000000-6248e38b2eb22b778c0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-a1b74c86531f42a9847aSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00177 +/- 0.00005 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000442 +/- 0.00059 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023409
KNApSAcK IDNot Available
Chemspider ID10128353
KEGG Compound IDC14813
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11954058
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zosmer A, Elder MG, Sullivan MH: The regulation of arachidonic acid metabolism in human first trimester trophoblast by cyclic AMP. Prostaglandins Other Lipid Mediat. 2003 Apr;71(1-2):43-53. [PubMed:12749593 ]
  2. Zosmer A, Elder MG, Sullivan MH: The production of progesterone and 5,6-epoxyeicosatrienoic acid by human granulosa cells. J Steroid Biochem Mol Biol. 2002 Aug;81(4-5):369-76. [PubMed:12361727 ]
  3. Hasunuma K, Terano T, Tamura Y, Yoshida S: Formation of epoxyeicosatrienoic acids from arachidonic acid by cultured rat aortic smooth muscle cell microsomes. Prostaglandins Leukot Essent Fatty Acids. 1991 Mar;42(3):171-5. [PubMed:1650001 ]

Only showing the first 10 proteins. There are 24 proteins in total.

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:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
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
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
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.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81

Only showing the first 10 proteins. There are 24 proteins in total.