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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 23:57:32 UTC
Update Date2022-03-07 02:49:21 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
Thumb
Synonyms
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:18034171 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]