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Record Information
Version3.6
Creation Date2007-05-22 19:11:00 UTC
Update Date2016-02-11 01:07:26 UTC
HMDB IDHMDB06245
Secondary Accession Numbers
  • HMDB11642
Metabolite Identification
Common Name18-Hydroxyarachidonic acid
Description(18R)-Hydroxyarachidonate is a substrate for CYP4F8 or leukotriene-B4 20-monooxygenase (EC 1.14.13.30). This enzyme hydroxylates arachdonic acid (20:4n-6) to (18R)-hydroxyarachidonate in the endoplasmic reticulum. This reaction is irreversible. CYP4F8 is a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and functions as a 19-hydroxylase of prostaglandins in seminal vesicles. In particular, CYP4F8 catalyzes the 2-hydroxylation of PGH1 and PGH2, which will lead to biosynthesis of the two main PGs of human seminal fluid, (19R)-hydroxy-PGE1 and (19R)-hydroxy-PGE2 (PMID: 10791960 ). 18-Hydroxyarachidonic acid is an intermediate in eicosanoid metabolism.
Structure
Thumb
Synonyms
ValueSource
(18R)-HydroxyarachidonateHMDB
(18R)-Hydroxyarachidonic acidHMDB
18(R)-HydroxyeicosatetraenoateHMDB
18(R)-Hydroxyeicosatetraenoic acidHMDB
18-HETEHMDB
18-HydroxyarachidonateHMDB
18-HydroxyeicosatetraenoateHMDB
18-Hydroxyeicosatetraenoic acidHMDB
Omega-hydroxyarachidonic acidHMDB
W-Hydroxyarachidonic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name18-hydroxy-arachidonic acid
CAS Registry Number133268-58-3
SMILES
CC[C@@H](O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-/t19-/m1/s1
InChI KeyInChIKey=PPCHNRUZQWLEMF-LFFPGIGVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and 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
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 mg/mLALOGPS
logP5.81ALOGPS
logP5.2ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.62 m3·mol-1ChemAxon
Polarizability38.21 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000273 +/- 4.7E-5 uMAdult (>18 years old)BothNormal details
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 IDFDB023857
KNApSAcK IDNot Available
Chemspider ID9316866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2300206
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06245
Metagene LinkHMDB06245
METLIN IDNot Available
PubChem Compound11141754
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceRomanov, Stepan G.; Ivanov, Igor V.; Groza, Nataliya V.; Kuhn, Hartmut; Myagkova, Galina I. Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids. Tetrahedron (2002), 58(42), 8483-8487.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bylund J, Hidestrand M, Ingelman-Sundberg M, Oliw EH: Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides. J Biol Chem. 2000 Jul 21;275(29):21844-9. [10791960 ]

Enzymes

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
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