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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2021-09-14 15:48:05 UTC
HMDB IDHMDB0002314
Secondary Accession Numbers
  • HMDB0002330
  • HMDB0011139
  • HMDB02314
  • HMDB02330
  • HMDB11139
Metabolite Identification
Common Name11,12-DiHETrE
Description11,12-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Arachidonic acid may be oxygenated by cytochrome P450 in several ways. Epoxidation of the double bonds leads to the regio- and enantioselective formation of four epoxyeicosatrienoic acids (EETs), which are hydrolyzed by epoxide hydrolase to vicinal diols (DHETs). 11,12-DiHETrE excretion is increased in healthy pregnant women compared with nonpregnant female volunteers, and increased even further in patients with pregnancy-induced hypertension (PIH). The physiological significance of arachidonic acid epoxides has been debated and it is unknown whether they play a role in pregnancy and parturition. Vasodilative effects, inhibition of cyclooxygenase, or inhibition of platelet aggregation by EETs have been observed only at micromolar concentrations. On the other hand, effects on the stimulus-secretion coupling during hormone release have been found in the nanomolar and picomolar range. (PMID: 9440131 , 2198572 ).
Structure
Data?1582752243
Synonyms
ValueSource
(+/-)11,12-dihetreChEBI
(5Z,8Z,14Z)-11,12-Dihydroxyeicosa-5,8,14-trienoic acidChEBI
(5Z,8Z,14Z)-11,12-Dihydroxyicosa-5,8,14-trienoic acidChEBI
11,12-DHETChEBI
11,12-Dihydroxy-5Z,8Z,14Z-eicosatrienoic acidChEBI
11,12-Dihydroxyeicosatrienoic acidChEBI
(5Z,8Z,14Z)-11,12-Dihydroxyeicosa-5,8,14-trienoateGenerator
(5Z,8Z,14Z)-11,12-Dihydroxyicosa-5,8,14-trienoateGenerator
11,12-Dihydroxy-5Z,8Z,14Z-eicosatrienoateGenerator
11,12-DihydroxyeicosatrienoateGenerator
(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoateHMDB
(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoic acidHMDB
12-Dihydroxyicosa-5,8,14-trienoateHMDB
12-Dihydroxyicosa-5,8,14-trienoic acidHMDB
11,12-DiHETEHMDB
Chemical FormulaC20H34O4
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
IUPAC Name(5Z,8Z,14Z)-11,12-dihydroxyicosa-5,8,14-trienoic acid
Traditional Name11,12-DiHETrE
CAS Registry Number192461-95-3
SMILES
CCCCC\C=C/CC(O)C(O)C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)/b8-6-,12-9-,13-10-
InChI KeyLRPPQRCHCPFBPE-KROJNAHFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(5.41) g/LALOGPS
logP10(4.49) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.87 m³·mol⁻¹ChemAxon
Polarizability39.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.43431661259
DarkChem[M-H]-188.25631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11,12-DiHETrE,1TMS,#1CCCCC/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O2799.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,1TMS,#2CCCCC/C=C\CC(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2798.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,1TMS,#3CCCCC/C=C\CC(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2722.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,2TMS,#1CCCCC/C=C\CC(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2799.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,2TMS,#2CCCCC/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2741.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,2TMS,#3CCCCC/C=C\CC(O)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2743.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,3TMS,#1CCCCC/C=C\CC(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2727.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,1TBDMS,#1CCCCC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O3053.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,1TBDMS,#2CCCCC/C=C\CC(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3052.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,1TBDMS,#3CCCCC/C=C\CC(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2972.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,2TBDMS,#1CCCCC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3233.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,2TBDMS,#2CCCCC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3212.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,2TBDMS,#3CCCCC/C=C\CC(O)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3211.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
11,12-DiHETrE,3TBDMS,#1CCCCC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3424.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11,12-DiHETrE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r5-3932000000-b03cec0d711590c8d0212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11,12-DiHETrE GC-MS (3 TMS) - 70eV, Positivesplash10-02bo-9235750000-f80395fc06d62412eeb02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11,12-DiHETrE 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 - 11,12-DiHETrE 10V, Positive-QTOFsplash10-00di-0119000000-10cf03f1745950d9d59d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 20V, Positive-QTOFsplash10-0h90-2912000000-883c5d41bece69d07c382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 40V, Positive-QTOFsplash10-0kg6-9600000000-aeed626e2130ac19513a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 10V, Negative-QTOFsplash10-000i-0019000000-c52d7900f0f0946dc76d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 20V, Negative-QTOFsplash10-00ku-0925000000-a2afd47eefbb62fb0dd82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 40V, Negative-QTOFsplash10-0a4i-7910000000-b20dcace15759c03d3252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 10V, Negative-QTOFsplash10-000i-0009000000-15ed63c1d23bf9978f522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 20V, Negative-QTOFsplash10-014r-0927000000-21cf53b8812ca42f66242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 40V, Negative-QTOFsplash10-0002-5930000000-e6ffb6bba915426c02472021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 10V, Positive-QTOFsplash10-0fk9-0209000000-d61f5c6da37a83faac6a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 20V, Positive-QTOFsplash10-0uk9-9838000000-4a3c577ad8d4500eb9592021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11,12-DiHETrE 40V, Positive-QTOFsplash10-0apl-9400000000-daeb65ba28296d545aed2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000513 +/- 0.000094 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000779 +/- 0.000037 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.001095 +/- 0.000433 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000566 +/- 0.0002 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00005 +/- 0.00003 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022961
KNApSAcK IDNot Available
Chemspider ID4446270
KEGG Compound IDC14774
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283146
PDB IDNot Available
ChEBI ID63969
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. Schaefer WR, Werner K, Schweer H, Schneider J, Arbogast E, Zahradnik HP: Cytochrome P450 metabolites of arachidonic acid in human placenta. Prostaglandins. 1997 Oct;54(4):677-87. [PubMed:9440131 ]
  2. Catella F, Lawson JA, Fitzgerald DJ, FitzGerald GA: Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension. Proc Natl Acad Sci U S A. 1990 Aug;87(15):5893-7. [PubMed:2198572 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:
EPHX2
Uniprot ID:
P34913
Molecular weight:
62615.22
Reactions
11,12-Epoxyeicosatrienoic acid + Water → 11,12-DiHETrEdetails