Human Metabolome Database Version 3.5

Showing metabocard for 12(R)-HPETE (HMDB04692)

Record Information
Version 3.5
Creation Date 2006-08-13 18:36:18 -0600
Update Date 2013-05-29 13:40:49 -0600
HMDB ID HMDB04692
Secondary Accession Numbers None
Metabolite Identification
Common Name 12(R)-HPETE
Description 12(R)-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 act in sequence to convert arachidonic acid via 12(R)-HPETE to 12(R)-HETE and the corresponding epoxyalcohol, 8(R)-hydroxy-11(R),12(R)-epoxyeicosatrienoic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 are the gene products of ALOX12B and ALOXE3. Mutations in ALOXE3 or ALOX12B have been found in families with autosomal-recessive congenital ichthyosis (ARCI). ARCI is a clinically and genetically heterogeneous group of severe hereditary keratinization disorders characterized by intense scaling of the whole integument, and differences in color and shape, often associated with erythema. Mutations in ALOXE3 and ALOX12B on chromosome 17p13, which code for two different epidermal lipoxygenases, were found in patients with ichthyosiform erythroderma. Genetic studies indicated that 12R-lipoxygenase (12R-LOX) or epidermal lipoxygenase-3 (eLOX3) was mutated in six families affected by non-bullous congenital ichthyosiform erythroderma (NCIE), one of the main clinical forms of ichthyosis. (PMID: 16116617 Link_out, 15629692 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 12R-HpETE
  2. 12R-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoate
  3. 12R-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
  4. 12R-Hydroperoxyeicosatetraenoate
  5. 12R-Hydroperoxyeicosatetraenoic acid
Chemical Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
IUPAC Name (5Z,8Z,10E,12R,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
Traditional IUPAC Name 12R-HpETE
CAS Registry Number 126873-49-2
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-/m1/s1
InChI Key ZIOZYRSDNLNNNJ-ZYBDYUKJSA-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 Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
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 39.88 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023408
KNApSAcK ID Not Available
Chemspider ID 7827808 Link_out
KEGG Compound ID C14812 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04692 Link_out
Metagene Link HMDB04692 Link_out
METLIN ID Not Available
PubChem Compound 9548885 Link_out
PDB ID Not Available
ChEBI ID 34145 Link_out
References
Synthesis Reference Porter, Ned A.; Dussault, Patrick; Breyer, Robert A.; Kaplan, Jere; Morelli, Joseph. The resolution of racemic hydroperoxides: a chromatography-based separation of perketals derived from arachidonic, linoleic, and oleic acid hydroperoxides. Chemical Research in Toxicology (1990), 3(3), 236-43.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Eckl KM, Krieg P, Kuster W, Traupe H, Andre F, Wittstruck N, Furstenberger G, Hennies HC: Mutation spectrum and functional analysis of epidermis-type lipoxygenases in patients with autosomal recessive congenital ichthyosis. Hum Mutat. 2005 Oct;26(4):351-61. Pubmed: 16116617 Link_out
  2. Yu Z, Schneider C, Boeglin WE, Brash AR: Mutations associated with a congenital form of ichthyosis (NCIE) inactivate the epidermal lipoxygenases 12R-LOX and eLOX3. Biochim Biophys Acta. 2005 Jan 5;1686(3):238-47. Pubmed: 15629692 Link_out

Enzymes
Name: Arachidonate 12-lipoxygenase, 12R-type
Reactions: Not Available
Gene Name: ALOX12B
Uniprot ID: O75342 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA