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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 23:57:32 UTC
Update Date2019-10-11 17:03:37 UTC
HMDB IDHMDB0004670
Secondary Accession Numbers
  • HMDB0010223
  • HMDB04670
  • HMDB10223
Metabolite Identification
Common Namealpha-Dimorphecolic acid
Descriptionalpha-Dimorphecolic acid or 9(S)-HODE is an endogenous fatty acid (PPAR)gamma agonist synthesized in the body from linoleic acid. alpha-Dimorphecolic acid 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 acid is a ligand of the G protein-coupled receptor G2A (PMID: 10073956 , 16647253 , 16236715 ). alpha-Dimorphecolic acid inhibits the proliferation of NHEK cells by suppressing DNA synthesis and arresting the cell cycle in the G0/1-phase. alpha-Dimorphecolic acid-G2A signalling plays proinflammatory roles in the skin under oxidative conditions (PMID: 18034171 ).
Structure
Data?1570813417
Synonyms
ValueSource
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoic acidChEBI
(9S)-Hydroxyoctadecadienoic acidChEBI
(9S)-Hydroxyoctadecadinoiec acidChEBI
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoateGenerator
(9S)-HydroxyoctadecadienoateGenerator
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoateGenerator
a-DimorphecolateGenerator, HMDB
a-Dimorphecolic acidGenerator, HMDB
alpha-DimorphecolateGenerator, HMDB
α-dimorphecolateGenerator, HMDB
α-dimorphecolic acidGenerator, HMDB
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acidHMDB
9(S)-HODEHMDB
9S-Hydroxy-10E,12Z-octadecadienoateHMDB
9S-Hydroxy-10E,12Z-octadecadienoic acidHMDB
alpha-DimorphecolicHMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoateHMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoic acidHMDB
9-Hydroxy-10,12-octadecadienoic acidMeSH, HMDB
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomerMeSH, HMDB
9-HODEMeSH, HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomerMeSH, HMDB
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomerMeSH, HMDB
9-Hydroxylinoleic acidMeSH, HMDB
Dimorphecolic acidMeSH, HMDB
9-OH-18:2DElta(10t,12t)MeSH, HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomerMeSH, HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomerMeSH, HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomerMeSH, HMDB
9-Hydroxyoctadecadienoic acidMeSH, HMDB
9S-HOD acidMeSH, HMDB
(+)-alpha-Dimorphecolic acidHMDB
(+)-α-Dimorphecolic acidHMDB
(10E,12Z)-9-Hydroxy-10,12-octadecadienoic acidHMDB
(9S,10E,12Z)-9-Hydroxy-10,12-octadecadienoic acidHMDB
(±)-alpha-Dimorphecolic acidHMDB
(±)-α-Dimorphecolic acidHMDB
9-(E,Z)-HODEHMDB
9-Hydroxy-(10E,12Z)-octadeca-10,12-dienoic acidHMDB
9-Hydroxy-10(E),12(Z)-octadecadienoic acidHMDB
9-Hydroxy-10-trans,12-cis-octadecadienoic acidHMDB
9S-HODEHMDB
alpha-Dimorphecolic acidHMDB
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
Traditional Nameα-dimorphecolic
CAS Registry Number73543-67-6
SMILES
CCCCC\C=C/C=C/[C@@H](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+/t17-/m1/s1
InChI KeyNPDSHTNEKLQQIJ-UINYOVNOSA-N
Chemical Taxonomy
Description 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
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability37.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4930000000-e1186c721ea6fb1169c7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9133100000-615fce6d28e837fb087eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-9edfb0d1ce954a62c742JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-6590000000-bf044894de0d32745a88JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9210000000-3859d2d1305a9293e4ceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-cb87e5a91d0ade94a4daJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1290000000-b10feffea7912d994743JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9620000000-a030dd65d92c57156f49JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0068 +/- 0.00167 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00965 +/- 0.00278 uMAdult (>18 years old)Not Specified
Normal
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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB07302
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003060
KNApSAcK IDNot Available
Chemspider ID4472255
KEGG Compound IDC14767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link9-Hydroxyoctadecadienoic_acid
METLIN IDNot Available
PubChem Compound5312830
PDB ID9HO
ChEBI ID34496
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:18034171 ]
  2. 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. [PubMed:10073956 ]
  3. 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. [PubMed:16647253 ]
  4. 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. [PubMed:16236715 ]