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Record Information
Version2.0
Created at2022-03-17 19:31:47 UTC
Updated at2022-03-17 19:31:47 UTC
NP-MRD IDNP0045556
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-HETE
Description5-HETE, also known as 5S-HETE, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 5-HETE is considered to be an eicosanoid lipid molecule. 5-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-HETE exists in all living organisms, ranging from bacteria to humans. Oxidized glutathione and 5-HETE can be biosynthesized from glutathione and 5-HPETE; which is catalyzed by the enzyme glutathione peroxidase 1. In humans, 5-HETE is involved in mefenamic acid action pathway. Outside of the human body, 5-HETE has been detected, but not quantified in, corns. This could make 5-HETE a potential biomarker for the consumption of these foods. 5-HETE is found in Homo sapiens, Lithothamnion corallioides and Mus musculus. 5-HETE was first documented in 1980 (PMID: 6253824). The activity of this product has not yet been fully evaluated (PMID: 3088130) (PMID: 3017333) (PMID: 6411852) (PMID: 7159548) (PMID: 2836505) (PMID: 15893379).
Structure
Thumb
Synonyms
ValueSource
5-HydroxyeicosatetraenoateKegg
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acidKegg
5-Hydroxyeicosatetraenoic acidGenerator
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoateGenerator
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidHMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidHMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acidHMDB
5(S)-Hydroxyeicosatetraenoic acidHMDB
5S-HETEHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateHMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateHMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoateHMDB
5(S)-HydroxyeicosatetraenoateHMDB
5(S)-HETEHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoateHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomerHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acidHMDB
FA(20:4(5-OH,6E,8Z,11Z,14Z))HMDB
FA(20:4(5S-OH,6E,8Z,11Z,14Z))HMDB
5-HETEHMDB
Chemical FormulaC20H32O3
Average Mass320.4663 Da
Monoisotopic Mass320.23514 Da
IUPAC Name(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
Traditional Name5-hydroxyeicosatetraenoic acid
CAS Registry Number70608-72-9
SMILES
CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChI KeyKGIJOOYOSFUGPC-JGKLHWIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lithothamnion corallioides--
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.88ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011134
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001434
KNApSAcK IDC00000423
Chemspider ID4444314
KEGG Compound IDC04805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Hydroxyeicosatetraenoic_acid
METLIN ID6554
PubChem Compound5280733
PDB IDNot Available
ChEBI ID28209
Good Scents IDNot Available
References
General References
  1. Kragballe K, Desjarlais L, Duell EA, Voorhees JJ: In vitro synthesis of 12-hydroxy-eicosatetraenoic acid is increased in uninvolved psoriatic epidermis. J Invest Dermatol. 1986 Jul;87(1):47-52. doi: 10.1111/1523-1747.ep12523561. [PubMed:3088130 ]
  2. Kanaji K, Okuma M, Sugiyama T, Sensaki S, Ushikubi F, Uchino H: Requirement of free arachidonic acid for leukotriene B4 biosynthesis by 12-hydroperoxyeicosatetraenoic acid-stimulated neutrophils. Biochem Biophys Res Commun. 1986 Jul 31;138(2):589-95. doi: 10.1016/s0006-291x(86)80537-x. [PubMed:3017333 ]
  3. Pawlowski NA, Kaplan G, Hamill AL, Cohn ZA, Scott WA: Arachidonic acid metabolism by human monocytes. Studies with platelet-depleted cultures. J Exp Med. 1983 Aug 1;158(2):393-412. doi: 10.1084/jem.158.2.393. [PubMed:6411852 ]
  4. Sasaki T, Asano T, Takakura K, Sano K, Nakamura T, Suzuki N, Imabayashi S, Ishikawa Y: [Cerebral vasospasm and lipid peroxidation--lipid peroxides in the cerebrospinal fluid after subarachnoid hemorrhage]. No To Shinkei. 1982 Dec;34(12):1191-6. [PubMed:7159548 ]
  5. Hoffman T, Lizzio EF, Suissa J, Rotrosen D, Sullivan JA, Mandell GL, Bonvini E: Dual stimulation of phospholipase activity in human monocytes. Role of calcium-dependent and calcium-independent pathways in arachidonic acid release and eicosanoid formation. J Immunol. 1988 Jun 1;140(11):3912-8. [PubMed:2836505 ]
  6. Powell WS, Rokach J: Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE. Prog Lipid Res. 2005 Mar-May;44(2-3):154-83. doi: 10.1016/j.plipres.2005.04.002. Epub 2005 Apr 20. [PubMed:15893379 ]
  7. Sud'ina GF, Kobel'kov GM, Barskii OA, Varfolomeev SD: [A kinetic scheme of human neutrophil 5-lipoxygenase activity]. Biokhimiia. 1990 Oct;55(10):1795-811. [PubMed:1964097 ]
  8. Bigby TD, Meslier N: Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol. 1989 Sep 15;143(6):1948-54. [PubMed:2550547 ]
  9. Brinkman HJ, van Buul-Wortelboer MF, van Mourik JA: Selective conversion and esterification of monohydroxyeicosatetraenoic acids by human vascular smooth muscle cells: relevance to smooth muscle cell proliferation. Exp Cell Res. 1991 Jan;192(1):87-92. doi: 10.1016/0014-4827(91)90161-m. [PubMed:1984423 ]
  10. Soter NA: The skin in mastocytosis. J Invest Dermatol. 1991 Mar;96(3):32S-38S; discussion 38S-39S. [PubMed:1672136 ]
  11. Chabannes B, Poubelle PE, Moliere P, De Medicis R, Lussier A, Lagarde M: Platelets abrogate leukotriene B(4) generation by human blood neutrophils stimulated with monosodium urate monohydrate or f-Met-Leu-Phe in vitro. Lab Invest. 2003 Apr;83(4):491-9. doi: 10.1097/01.lab.0000062855.90029.d8. [PubMed:12695552 ]
  12. Hosni M, Meskini N, Prigent AF, Anker G, Joulain C, el Habib R, Lagarde M: Diethyldithiocarbamate (ditiocarb sodium) effect on arachidonic acid metabolism in human mononuclear cells. Glutathione peroxidase-like activity. Biochem Pharmacol. 1992 Mar 17;43(6):1319-29. doi: 10.1016/0006-2952(92)90509-h. [PubMed:1314059 ]
  13. Maderna P, Colli S, Caruso D, Eligini S, Toia A, Galli G, Tremoli E: Quantitative changes of hydroxyacid formation during platelet-neutrophil interaction. J Lab Clin Med. 1993 Mar;121(3):406-14. [PubMed:8383163 ]
  14. Goetzl EJ: Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov 13;288(5787):183-5. doi: 10.1038/288183a0. [PubMed:6253824 ]
  15. Marcus AJ, Safier LB, Broekman MJ, Ullman HL, Islam N, Sorrell TC, Serhan CN, Weissmann G, Oglesby TD, Gorman RR: Production of metabolic products of arachidonic acid during cell-cell interactions. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 2):338-42. doi: 10.1016/0091-6749(84)90126-x. [PubMed:6088611 ]