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Record Information
Version4.0
Creation Date2006-05-22 14:17:47 UTC
Update Date2017-09-27 08:24:15 UTC
HMDB IDHMDB0002314
Secondary Accession Numbers
  • 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
Thumb
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-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
11,12-DHETHMDB
12-Dihydroxyicosa-5,8,14-trienoateHMDB
12-Dihydroxyicosa-5,8,14-trienoic acidHMDB
11,12-DiHETEMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical 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 Solubility0.013 g/LALOGPS
logP5.41ALOGPS
logP4.49ChemAxon
logS-4.4ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0119000000-10cf03f1745950d9d59dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-2912000000-883c5d41bece69d07c38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kg6-9600000000-aeed626e2130ac19513aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-c52d7900f0f0946dc76dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-0925000000-a2afd47eefbb62fb0dd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7910000000-b20dcace15759c03d325View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000513 +/- 9.4E-5 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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-EpETrE + Water → 11,12-DiHETrEdetails