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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2022-09-22 17:43:48 UTC
HMDB IDHMDB0002265
Secondary Accession Numbers
  • HMDB0002342
  • HMDB02265
  • HMDB02342
Metabolite Identification
Common Name14,15-DiHETrE
Description14,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR, shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031 , 16113065 ).
Structure
Data?1582752239
Synonyms
ValueSource
(5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoic acidChEBI
(5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoic acidChEBI
14,15-Dihydroxy-5Z,8Z,11Z-eicosatrienoic acidChEBI
14,15-Dihydroxyeicosatrienoic acidChEBI
(5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoateGenerator
(5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoateGenerator
14,15-Dihydroxy-5Z,8Z,11Z-eicosatrienoateGenerator
14,15-DihydroxyeicosatrienoateGenerator
(+/-)14,15-dihetreHMDB
14,15-DHETHMDB
Chemical FormulaC20H34O4
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
IUPAC Name(5Z,8Z,11Z)-14,15-dihydroxyicosa-5,8,11-trienoic acid
Traditional Name14,15-DiHETrE
CAS Registry Number77667-09-5
SMILES
CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24)/b6-4-,9-7-,13-10-
InChI KeySYAWGTIVOGUZMM-ILYOTBPNSA-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
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
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 Solubility0.014 g/LALOGPS
logP5.28ALOGPS
logP4.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.87 m³·mol⁻¹ChemAxon
Polarizability39.75 ųChemAxon
Number of Rings0ChemAxon
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]+188.83231661259
DarkChem[M-H]-189.61231661259
DeepCCS[M+H]+193.3130932474
DeepCCS[M-H]-190.95230932474
DeepCCS[M-2H]-223.83830932474
DeepCCS[M+Na]+199.40330932474
AllCCS[M+H]+192.432859911
AllCCS[M+H-H2O]+189.632859911
AllCCS[M+NH4]+194.932859911
AllCCS[M+Na]+195.632859911
AllCCS[M-H]-189.232859911
AllCCS[M+Na-2H]-191.232859911
AllCCS[M+HCOO]-193.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
14,15-DiHETrECCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O4230.8Standard polar33892256
14,15-DiHETrECCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O2401.0Standard non polar33892256
14,15-DiHETrECCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O2609.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
14,15-DiHETrE,1TMS,isomer #1CCCCCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O2810.9Semi standard non polar33892256
14,15-DiHETrE,1TMS,isomer #2CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2818.9Semi standard non polar33892256
14,15-DiHETrE,1TMS,isomer #3CCCCCC(O)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2723.7Semi standard non polar33892256
14,15-DiHETrE,2TMS,isomer #1CCCCCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2796.2Semi standard non polar33892256
14,15-DiHETrE,2TMS,isomer #2CCCCCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2741.7Semi standard non polar33892256
14,15-DiHETrE,2TMS,isomer #3CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2752.7Semi standard non polar33892256
14,15-DiHETrE,3TMS,isomer #1CCCCCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2735.4Semi standard non polar33892256
14,15-DiHETrE,1TBDMS,isomer #1CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O3065.3Semi standard non polar33892256
14,15-DiHETrE,1TBDMS,isomer #2CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3071.4Semi standard non polar33892256
14,15-DiHETrE,1TBDMS,isomer #3CCCCCC(O)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2973.3Semi standard non polar33892256
14,15-DiHETrE,2TBDMS,isomer #1CCCCCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3242.5Semi standard non polar33892256
14,15-DiHETrE,2TBDMS,isomer #2CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3215.9Semi standard non polar33892256
14,15-DiHETrE,2TBDMS,isomer #3CCCCCC(O)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)C3228.4Semi standard non polar33892256
14,15-DiHETrE,3TBDMS,isomer #1CCCCCC(O[Si](C)(C)C(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)C3440.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 14,15-DiHETrE GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-7492000000-53d0c760eca4ea7c74b72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14,15-DiHETrE GC-MS (3 TMS) - 70eV, Positivesplash10-00a9-9222530000-2b02e3de22d55ff2a4402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14,15-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 - 14,15-DiHETrE 10V, Positive-QTOFsplash10-00di-0019000000-7f7f92b8b0190b6752032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 20V, Positive-QTOFsplash10-00di-9554000000-c5755d9eb5a2aadcbe2c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 40V, Positive-QTOFsplash10-0597-9410000000-125ce6f656a7b73f6d932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 10V, Negative-QTOFsplash10-000i-0019000000-4e33cef8debb2f5475342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 20V, Negative-QTOFsplash10-00kr-5498000000-73635b3c1d4840cbee342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 40V, Negative-QTOFsplash10-0a4i-9340000000-922bf4ce3cb3318c6c5a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 10V, Positive-QTOFsplash10-0fki-0119000000-612a268dd6e2942a25c12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 20V, Positive-QTOFsplash10-0uk9-7329000000-bfc9aee45e6cf348ba912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 40V, Positive-QTOFsplash10-015c-9300000000-97a1e7b9e6ae50cf945d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 10V, Negative-QTOFsplash10-000i-0119000000-9311f411eaf67d8cf9e72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 20V, Negative-QTOFsplash10-0ap0-3797000000-bc04d7bd65d89f0a702d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14,15-DiHETrE 40V, Negative-QTOFsplash10-0002-9320000000-f39271ce850d20fe0f6a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.001449 +/- 0.000071 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000714 +/- 0.000031 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00122 +/- 0.000705 uMAdult (>18 years old)Not SpecifiedNormal
    • Oxygenated lipids...
details
BloodDetected and Quantified0.000603 +/- 0.00018 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00013 +/- 0.00006 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022935
KNApSAcK IDNot Available
Chemspider ID4446271
KEGG Compound IDC14775
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283147
PDB IDNot Available
ChEBI ID63966
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. Ng VY, Huang Y, Reddy LM, Falck JR, Lin ET, Kroetz DL: Cytochrome P450 eicosanoids are activators of peroxisome proliferator-activated receptor alpha. Drug Metab Dispos. 2007 Jul;35(7):1126-34. Epub 2007 Apr 12. [PubMed:17431031 ]
  2. Fang X, Hu S, Xu B, Snyder GD, Harmon S, Yao J, Liu Y, Sangras B, Falck JR, Weintraub NL, Spector AA: 14,15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-alpha. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H55-63. Epub 2005 Aug 19. [PubMed:16113065 ]

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
14,15-Epoxy-5,8,11-eicosatrienoic acid + Water → 14,15-DiHETrEdetails