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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 19:56:15 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0005998
Secondary Accession Numbers
  • HMDB05998
Metabolite Identification
Common Name20-Hydroxyeicosatetraenoic acid
Description20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor of renal, cerebral, and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase, and the mitogen-activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal, and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries. A fall in levels of 20-HETE contributes to the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries (PMID: 16258232 ).
Structure
Data?1582752370
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acidChEBI
20-Hydroxy arachidonic acidChEBI
20-Hydroxyarachidonic acidChEBI
20-Hydroxyicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoateGenerator
20-Hydroxy arachidonateGenerator
20-HydroxyarachidonateGenerator
20-HydroxyicosatetraenoateGenerator
20-HydroxyeicosatetraenoateGenerator
(all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoateHMDB
(all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
20-HETEHMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateHMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acidHMDB
20-Hydroxy-5,8,11,14-eicosatetraenoateHMDB
20-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoateHMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name20-hete
CAS Registry Number79551-86-3
SMILES
OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
InChI KeyNNDIXBJHNLFJJP-DTLRTWKJSA-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
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
Role
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 Solubility0.0012 g/LALOGPS
logP5.87ALOGPS
logP5.15ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.88 m³·mol⁻¹ChemAxon
Polarizability38.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.38131661259
DarkChem[M-H]-190.9931661259
DeepCCS[M+H]+187.73130932474
DeepCCS[M-H]-185.37330932474
DeepCCS[M-2H]-218.25930932474
DeepCCS[M+Na]+193.82430932474
AllCCS[M+H]+183.032859911
AllCCS[M+H-H2O]+180.132859911
AllCCS[M+NH4]+185.632859911
AllCCS[M+Na]+186.432859911
AllCCS[M-H]-185.232859911
AllCCS[M+Na-2H]-187.032859911
AllCCS[M+HCOO]-189.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
20-Hydroxyeicosatetraenoic acidOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O3964.3Standard polar33892256
20-Hydroxyeicosatetraenoic acidOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O2217.4Standard non polar33892256
20-Hydroxyeicosatetraenoic acidOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O2599.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
20-Hydroxyeicosatetraenoic acid,1TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O2826.4Semi standard non polar33892256
20-Hydroxyeicosatetraenoic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO2608.4Semi standard non polar33892256
20-Hydroxyeicosatetraenoic acid,2TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2694.4Semi standard non polar33892256
20-Hydroxyeicosatetraenoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O3045.0Semi standard non polar33892256
20-Hydroxyeicosatetraenoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO2863.7Semi standard non polar33892256
20-Hydroxyeicosatetraenoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3184.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-3290000000-c19c2446fd09c9b5b1142017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0g6s-8958400000-372a8a263c8ea8f0e5b02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic 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 - 20-Hydroxyeicosatetraenoic acid 10V, Positive-QTOFsplash10-0uk9-0059000000-650b772489866747dfc12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Positive-QTOFsplash10-0pdr-2293000000-4135e55c1f638956a1652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Positive-QTOFsplash10-0006-8890000000-7333663b79a20dc524352016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Negative-QTOFsplash10-014i-0039000000-b8b23d059895b0d514822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Negative-QTOFsplash10-0gb9-2098000000-7fd830563f4a43d0b8122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Negative-QTOFsplash10-0a4l-9040000000-ac722c9b6528d7965c212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Negative-QTOFsplash10-014i-0009000000-c55e430e69fa5c79a7472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Negative-QTOFsplash10-0gb9-1049000000-1b54cbfba7d53b2e17ab2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Negative-QTOFsplash10-006x-9151000000-9d68be1fa8ed76d657d42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Positive-QTOFsplash10-0uk9-1229000000-2c09f1a1c932d016c5e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Positive-QTOFsplash10-0fe1-5934000000-650155a4dedf606f20452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Positive-QTOFsplash10-00lu-7900000000-c13624e44921230c29082021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00177 +/- 0.00043 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00301 +/- 0.00193 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.00083 +/- 0.00015 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000917 +/- 0.00058 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0014 (0.00043-0.0053) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00037 +/- 0.00015 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
UrineDetected and Quantified0.0001 +/- 0.000019 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0037 (0.0013-0.0059) uMAdult (>18 years old)BothRenovascular disease details
BloodDetected and Quantified0.0028 (0.0012-0.0067) uMAdult (>18 years old)BothHypertension details
Cerebrospinal Fluid (CSF)Detected and Quantified0.009 +/-0.23 uMAdult (>18 years old)Both
Cerebral Vasospasm
details
UrineDetected and Quantified0.0045 (0.0015-0.0087) umol/mmol creatinineAdult (>18 years old)BothRenovascular disease details
Associated Disorders and Diseases
Disease References
Hypertension
  1. Minuz P, Jiang H, Fava C, Turolo L, Tacconelli S, Ricci M, Patrignani P, Morganti A, Lechi A, McGiff JC: Altered release of cytochrome p450 metabolites of arachidonic acid in renovascular disease. Hypertension. 2008 May;51(5):1379-85. doi: 10.1161/HYPERTENSIONAHA.107.105395. Epub 2008 Mar 31. [PubMed:18378855 ]
Cerebral vasospasm
  1. Poloyac SM, Reynolds RB, Yonas H, Kerr ME: Identification and quantification of the hydroxyeicosatetraenoic acids, 20-HETE and 12-HETE, in the cerebrospinal fluid after subarachnoid hemorrhage. J Neurosci Methods. 2005 Jun 15;144(2):257-63. Epub 2004 Dec 30. [PubMed:15910986 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023796
KNApSAcK IDNot Available
Chemspider ID4446281
KEGG Compound IDC14748
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link20-Hydroxyeicosatetraenoic acid
METLIN IDNot Available
PubChem Compound5283157
PDB IDNot Available
ChEBI ID34306
Food Biomarker OntologyNot Available
VMH IDWHARACHD
MarkerDB IDMDB00000479
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Miyata N, Roman RJ: Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system. J Smooth Muscle Res. 2005 Aug;41(4):175-93. [PubMed:16258232 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Molecular weight:
59347.31
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
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:
CYP4F2
Uniprot ID:
P78329
Molecular weight:
59852.825
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:
CYP4F3
Uniprot ID:
Q08477
Molecular weight:
59846.085
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
CYP4F11
Uniprot ID:
Q9HBI6
Molecular weight:
60145.165
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Hydroxylates arachidonic acid (20:4n-6) to (18R)-hydroxyarachidonate. Shows little activity against prostaglandin (PG) D2, PGE1, PGE2, PGF2alpha, and leukotriene B4. Catalyzes omega-2 and omega-3-hydroxylation of PGH1 and PGH2. Catalyzes epoxidation of 4,7,10,13,16,19-(Z)-docosahexaenoic acid (22:6n-3) and 7,10,13,16,19-(Z)-docosapentaenoic acid (22:5n-3) and omega-3-hydroxylation of 4,7,10,13,16-(Z)-docosapentaenoic acid (22:5n-6). Catalyzes hydroxylation of PGI2 and carbaprostacyclin.
Gene Name:
CYP4F8
Uniprot ID:
P98187
Molecular weight:
59993.995
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:
CYP4A22
Uniprot ID:
Q5TCH4
Molecular weight:
59245.28
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4F22
Uniprot ID:
Q6NT55
Molecular weight:
Not Available
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails