Showing metabocard for 12(S)-HPETE (HMDB04243)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version3.6
Creation Date2006-08-13 15:05:29 UTC
Update Date2013-02-09 00:13:07 UTC
HMDB IDHMDB04243
Secondary Accession NumbersNone
Metabolite Identification
Common Name12(S)-HPETE
Description12-HPETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Leukotrienes). Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (+/-)12-HETE. A family of biologically active compounds derived from arachidonic acid by oxidative metabolism through the 5-lipoxygenase pathway. They participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. They have potent actions on many essential organs and systems, including the cardiovascular, pulmonary, and central nervous system as well as the gastrointestinal tract and the immune system.
Structure
Thumb
MOLSDFPDBSMILESInChIView Structure
Synonyms
  1. (5Z,8z,10e,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
  2. (5Z,8z,10e,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
  3. 12-Hpete
  4. 12-Hydroperoxyeicosatetraenoate
  5. 12-Hydroperoxyeicosatetraenoic acid
  6. 12-Hydroperoxyicosatetraenoate
  7. 12-Hydroperoxyicosatetraenoic acid
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
Traditional IUPAC Name12-hpete
CAS Registry Number71774-10-2
SMILES
CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
InChI KeyZIOZYRSDNLNNNJ-LQWMCKPYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroperoxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroperoxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
  • Hydroperoxide
Direct ParentHydroperoxyeicosatetraenoic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0017 g/LALOGPS
logP5.9ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (strongest acidic)4.89ChemAxon
pKa (strongest basic)-4.2ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area66.76ChemAxon
rotatable bond count15ChemAxon
refractivity102.82ChemAxon
polarizability39.12ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified1.45 +/- 2.3 uMAdult (>18 years old)Not SpecifiedCommentNormal
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 IDFDB023348
KNApSAcK IDNot Available
Chemspider ID4444415
KEGG Compound IDC05965
BioCyc IDNot Available
BiGG ID44618
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04243
Metagene LinkHMDB04243
METLIN ID7038
PubChem Compound5280892
PDB IDNot Available
ChEBI ID15626
References
Synthesis ReferenceNagata, Ryu; Kawakami, Masayuki; Matsuura, Teruo; Saito, Isao. Synthesis of 12-hydroperoxyeicosatetraenoic acid (12-HPETE). On the stereochemistry in the conversion of 12(S)-HETE to 12-HPETE. Tetrahedron Letters (1989), 30(21), 2817-20.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boutaud O, Aronoff DM, Richardson JH, Marnett LJ, Oates JA: Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H(2) synthases. Proc Natl Acad Sci U S A. 2002 May 14;99(10):7130-5. Pubmed: 12011469

Enzymes

1. Arachidonate 12-lipoxygenase, 12S-type
Gene Name:
ALOX12
Uniprot ID:
P18054
Reactions
Arachidonic acid + Oxygen unknown 12(S)-HPETEdetails