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Human Metabolome Database Version 3.5

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

Record Information
Version 3.5
Creation Date 2006-08-13 09:05:29 -0600
Update Date 2013-02-08 17:13:07 -0700
HMDB ID HMDB04243
Secondary Accession Numbers None
Metabolite Identification
Common Name 12(S)-HPETE
Description 12-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D 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 Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
IUPAC Name (5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
Traditional IUPAC Name 12-hpete
CAS Registry Number 71774-10-2
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 Key ZIOZYRSDNLNNNJ-LQWMCKPYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroperoxyeicosatetraenoic 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 Parent Hydroperoxyeicosatetraenoic Acids
Ontology
Status Detected 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
State Liquid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0017 g/L ALOGPS
LogP 5.90 ALOGPS
LogP 5.81 ChemAxon
LogS -5.30 ALOGPS
pKa (strongest acidic) 4.89 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 102.82 ChemAxon
Polarizability 39.12 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.45 +/- 2.3 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023348
KNApSAcK ID Not Available
Chemspider ID 4444415 Link_out
KEGG Compound ID C05965 Link_out
BioCyc ID Not Available
BiGG ID 44618 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB04243 Link_out
Metagene Link HMDB04243 Link_out
METLIN ID 7038 Link_out
PubChem Compound 5280892 Link_out
PDB ID Not Available
ChEBI ID 15626 Link_out
References
Synthesis Reference Nagata, 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) Download (PDF)
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 Link_out
Enzymes
Name: Arachidonate 12-lipoxygenase, 12S-type
Reactions:
  • arachidonate + O2 = (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate [RN:R01596]
Gene Name: ALOX12
Uniprot ID: P18054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA