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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-19 12:44:39 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005050
Secondary Accession Numbers
  • HMDB0004683
  • HMDB04683
  • HMDB05050
Metabolite Identification
Common Name15H-11,12-EETA
Description15H-11,12-EETA is an epoxyeicosatrienoic acid (EET). The role of EETs in regulation of the cerebral circulation has become more important, since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence hve shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes. (PMID: 17494091 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 , 11413051 , 10519554 , 11893556 ).
Structure
Data?1582752343
Synonyms
ValueSource
15-Hydroxy-11,12-epoxyeicosatrienoic acidKegg
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoic acidKegg
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoic acidKegg
15-Hydroxy-11,12-epoxyeicosatrienoateGenerator
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoateGenerator
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoateGenerator
(+/-)11,12-ep-15(S)-hetreHMDB
11,12-Epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoateHMDB
11,12-Epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoic acidHMDB
15-H-11,12-EETAHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
Traditional Name(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
CAS Registry Number877878-78-9
SMILES
CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-9-12-17(21)15-16-19-18(24-19)13-10-7-5-4-6-8-11-14-20(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+/t17-,18?,19?/m0/s1
InChI KeyGELFSVXLSDZDHE-YZSNCDGGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP5.35ALOGPS
logP4.57ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.72 m³·mol⁻¹ChemAxon
Polarizability39.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.57331661259
DarkChem[M-H]-187.90631661259
DeepCCS[M+H]+190.85930932474
DeepCCS[M-H]-188.50130932474
DeepCCS[M-2H]-221.38730932474
DeepCCS[M+Na]+196.95230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15H-11,12-EETACCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O3967.4Standard polar33892256
15H-11,12-EETACCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O2382.4Standard non polar33892256
15H-11,12-EETACCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O2652.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15H-11,12-EETA,1TMS,isomer #1CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2754.8Semi standard non polar33892256
15H-11,12-EETA,1TMS,isomer #2CCCCC[C@H](O)/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2659.2Semi standard non polar33892256
15H-11,12-EETA,2TMS,isomer #1CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2706.3Semi standard non polar33892256
15H-11,12-EETA,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2996.7Semi standard non polar33892256
15H-11,12-EETA,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2910.3Semi standard non polar33892256
15H-11,12-EETA,2TBDMS,isomer #1CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3211.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15H-11,12-EETA GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9882000000-3542c00b22d7a628f9982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15H-11,12-EETA GC-MS (2 TMS) - 70eV, Positivesplash10-00vr-9283200000-71f2061c2c545719c5e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15H-11,12-EETA GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15H-11,12-EETA 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 - 15H-11,12-EETA 10V, Negative-QTOFsplash10-000i-0019000000-5d21765fe085158726492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Negative-QTOFsplash10-014r-2469000000-e74f5db2ba7aafe7ac692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Negative-QTOFsplash10-052f-9600000000-5f3ccdc5aeb81ec5bee72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 10V, Negative-QTOFsplash10-00kr-0109000000-a81cf651f2bb9ef3b6b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Negative-QTOFsplash10-00kr-0459000000-b65496bff68de53bdb692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Negative-QTOFsplash10-052f-8941000000-395c49b790cb96398dc22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 10V, Positive-QTOFsplash10-014i-0119000000-6669e73fed08fa686b6e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Positive-QTOFsplash10-0g6r-2923000000-e1ebfd6b5b07ef6842222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Positive-QTOFsplash10-0a4u-9820000000-9eb24537f07886109c992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 10V, Positive-QTOFsplash10-0gb9-0219000000-4a6493bd003dca0bbd4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Positive-QTOFsplash10-0uxr-5519000000-1d89d8ca3789431e87c22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Positive-QTOFsplash10-014l-9600000000-db7302e43cd74c6250d32021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023612
KNApSAcK IDNot Available
Chemspider ID10128337
KEGG Compound IDC14781
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11954042
PDB IDNot Available
ChEBI ID34160
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lipid Maps (LMFA03080007) [Link]

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.