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Record Information
Version3.6
Creation Date2008-09-15 09:55:19 UTC
Update Date2016-02-11 01:16:27 UTC
HMDB IDHMDB10223
Secondary Accession NumbersNone
Metabolite Identification
Common Name9-HODE
Description9-HODE, which is a trans isomer of 9(S)-HODE, is an endogenous fatty acid PPARgamma agonist synthesized in the body from linoleic acid. Alpha-dimorphecolic activates Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma in human endothelial cells increasing plasminogen activator inhibitor type-1 expression. Plasminogen activator inhibitor type-1 (PAI-1) is a major physiological inhibitor of fibrinolysis, with its plasma levels correlating with the risk for myocardial infarction and venous thrombosis. The regulation of PAI-1 transcription by endothelial cells (ECs), a major source of PAI-1, remains incompletely understood. Adipocytes also produce PAI-1, suggesting possible common regulatory pathways between adipocytes and ECs. Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma is a ligand-activated transcription factor that regulates gene expression in response to various mediators such as 15-deoxy-Delta12, 14-prostaglandin J2 (15d-PGJ2) and oxidized linoleic acid (9- and 13-HODE). Alpha-dimorphecolic is a ligand of the G protein-coupled receptor G2A. (PMID: 10073956 , 16647253 , 16236715 ). 9(S)-HODE inhibits proliferation of NHEK cells by suppressing DNA synthesis and arresting the cell cycle in the G0/1-phase. 9-HODE-G2A signaling plays proinflammatory roles in skin under oxidative conditions. (PMID: 18034171 )
Structure
Thumb
Synonyms
ValueSource
9-Hydroxy-10,12-octadecadienoateHMDB
9-Hydroxy-10,12-octadecadienoic acidHMDB
9-Hydroxy-10E,12E-octadecadienoateHMDB
9-Hydroxy-10E,12E-octadecadienoic acidHMDB
9-Hydroxy-trans-10,trans-12-octadecadienoateHMDB
9-Hydroxy-trans-10,trans-12-octadecadienoic acidHMDB
9-Hydroxylinoleic acidHMDB
alpha-Dimorphecolic acidHMDB
Dimorphecolic acidHMDB
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(10E,12E)-9-hydroxyoctadeca-10,12-dienoic acid
Traditional Namedimorphecolic acid
CAS Registry Number15514-85-9
SMILES
CCCCC\C=C\C=C\C(O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11+
InChI KeyInChIKey=NPDSHTNEKLQQIJ-SIGMCMEVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassLineolic acids and derivatives
Sub ClassNot Available
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • 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 DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Signaling
Application
  • Not Available
Cellular locations
  • Membrane (predicted from logP)
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 Solubility0.0032 mg/mLALOGPS
logP5.88ALOGPS
logP5.19ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m3·mol-1ChemAxon
Polarizability37.98 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00965 +/- 0.00278 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.0068 +/- 0.00167 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0117 +/- 0.00023 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.011 +/- 0.0061 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0065 +/- 0.00064 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4446072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10223
Metagene LinkHMDB10223
METLIN IDNot Available
PubChem Compound5282945
PDB IDNot Available
ChEBI ID595882
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Marx N, Bourcier T, Sukhova GK, Libby P, Plutzky J: PPARgamma activation in human endothelial cells increases plasminogen activator inhibitor type-1 expression: PPARgamma as a potential mediator in vascular disease. Arterioscler Thromb Vasc Biol. 1999 Mar;19(3):546-51. [10073956 ]
  2. Hampel JK, Brownrigg LM, Vignarajah D, Croft KD, Dharmarajan AM, Bentel JM, Puddey IB, Yeap BB: Differential modulation of cell cycle, apoptosis and PPARgamma2 gene expression by PPARgamma agonists ciglitazone and 9-hydroxyoctadecadienoic acid in monocytic cells. Prostaglandins Leukot Essent Fatty Acids. 2006 May;74(5):283-93. Epub 2006 May 2. [16647253 ]
  3. Obinata H, Hattori T, Nakane S, Tatei K, Izumi T: Identification of 9-hydroxyoctadecadienoic acid and other oxidized free fatty acids as ligands of the G protein-coupled receptor G2A. J Biol Chem. 2005 Dec 9;280(49):40676-83. Epub 2005 Oct 19. [16236715 ]
  4. Hattori T, Obinata H, Ogawa A, Kishi M, Tatei K, Ishikawa O, Izumi T: G2A plays proinflammatory roles in human keratinocytes under oxidative stress as a receptor for 9-hydroxyoctadecadienoic acid. J Invest Dermatol. 2008 May;128(5):1123-33. Epub 2007 Nov 22. [18034171 ]