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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2021-09-14 14:58:12 UTC
HMDB IDHMDB0002232
Secondary Accession Numbers
  • HMDB0004672
  • HMDB02232
  • HMDB04672
Metabolite Identification
Common Name8,9-Epoxyeicosatrienoic acid
Description8,9-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid eicosanoid, a metabolite of arachidonic acid. The P450 epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 ).
Structure
Data?1582752237
Synonyms
ValueSource
(+/-)8,9-epetreChEBI
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoic acidChEBI
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoic acidChEBI
8,9-Epoxy-5Z,11Z,14Z-eicosatrienoic acidChEBI
8,9-Epoxy-5Z,11Z,14Z-icosatrienoic acidChEBI
8,9-Epoxyicosatrienoic acidChEBI
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoateGenerator
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoateGenerator
8,9-Epoxy-5Z,11Z,14Z-eicosatrienoateGenerator
8,9-Epoxy-5Z,11Z,14Z-icosatrienoateGenerator
8,9-EpoxyicosatrienoateGenerator
8,9-EpoxyeicosatrienoateGenerator
8,9-EetHMDB
8,9-Epoxyeicosatrienoic acid, (2alpha(Z),3alpha(2Z,5Z))-isomerHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid
Traditional Name8,9-epoxyeicosatrienoic acid
CAS Registry Number81246-85-7
SMILES
CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,12-9-,13-10-
InChI KeyDBWQSCSXHFNTMO-TYAUOURKSA-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
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available184.633http://allccs.zhulab.cn/database/detail?ID=AllCCS00001862
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP10(6.25) g/LALOGPS
logP10(5.65) g/LChemAxon
logS10(-6) g/LALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity98.36 m³·mol⁻¹ChemAxon
Polarizability38.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.8131661259
DarkChem[M-H]-185.00831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8,9-Epoxyeicosatrienoic acid,1TMS,#1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)O[Si](C)(C)C2480.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-Epoxyeicosatrienoic acid,1TBDMS,#1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2724.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-Epoxyeicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000g-6980000000-07a990c3a66cfc7764e52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-Epoxyeicosatrienoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-002r-9553000000-120e27beab70feb84ed62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-Epoxyeicosatrienoic 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 - 8,9-Epoxyeicosatrienoic acid 10V, Positive-QTOFsplash10-0udi-0229000000-4a7644f998116e5959aa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Positive-QTOFsplash10-0wn9-4921000000-727677e385ebbb9958642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Positive-QTOFsplash10-015d-9500000000-903e4e69e6bda087561b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 10V, Negative-QTOFsplash10-014i-0219000000-80c9ec974d3aaabbc8b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Negative-QTOFsplash10-0gdi-1539000000-c3f531539781dda281682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Negative-QTOFsplash10-052f-9800000000-a8abb16134374c498d9d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 10V, Positive-QTOFsplash10-0uk9-4429000000-e15c713039784fb91bd62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Positive-QTOFsplash10-0fsi-9413000000-c06fd94936bbbdd11dd32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Positive-QTOFsplash10-05qc-9200000000-fd86608717f334cda9ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 10V, Negative-QTOFsplash10-014i-0009000000-5afdb8d651d23c147e452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Negative-QTOFsplash10-014i-0329000000-417e0056d0fd313e5a7b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Negative-QTOFsplash10-052f-9311000000-bae1c492ade35c4526422021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.0002 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000627 +/- 0.00071 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 IDFDB022920
KNApSAcK IDNot Available
Chemspider ID4446324
KEGG Compound IDC14769
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283203
PDB IDNot Available
ChEBI ID34490
Food Biomarker OntologyNot Available
VMH IDC14769
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fritscher LG, Post M, Rodrigues MT, Silverman F, Balter M, Chapman KR, Zamel N: Profile of eicosanoids in breath condensate in asthma and COPD. J Breath Res. 2012 Jun;6(2):026001. doi: 10.1088/1752-7155/6/2/026001. Epub 2012 Mar 27. [PubMed:22451217 ]

Only showing the first 10 proteins. There are 25 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 25 proteins in total.