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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 01:38:14 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004704
Secondary Accession Numbers
  • HMDB0031679
  • HMDB04704
  • HMDB31679
Metabolite Identification
Common Name9,10-DHOME
Description9,10-Dihydroxy-12-octadecenoic acid (CAS: 263399-34-4), also known as 9,10-DHOME, is a derivative of linoleic acid diol and has been reported to be toxic in human's tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10-EpOME. 9,10-EpOME act as a protoxin, with the corresponding epoxide hydrolase metabolite 9,10-DHOME, specifically exerting toxicity. Both 9,10-EpOME and 9,10-DHOME are shown to have neutrophil chemotactic activity. 9,10-DHOME suppresses the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation (PMID: 12021203 , 12127265 , 17435320 ). 9,10-DHOME is found in fruits and can be isolated from the seeds of Cucurbita pepo.
Structure
Thumb
Synonyms
ValueSource
(12Z)-9,10-Dihydroxy-12-octadecenoic acidHMDB
9,10-DiHOMEHMDB
9,10-Dihydroxy-12Z-octadecenoic acidHMDB
9,10-Dihydroxy-12-octadecenoic acidHMDB
(9R,10R)-Dihydroxy-12(Z)-octadecenoic acidHMDB
(R,R)-9,10-Dihydroxy-cis-12-octadecenoic acidHMDB
9,10-DHOMEHMDB
Chemical FormulaC18H34O4
Average Molecular Weight314.466
Monoisotopic Molecular Weight314.245709575
IUPAC Name(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid
Traditional Name(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid
CAS Registry Number125356-86-7
SMILES
CCCCC\C=C/C[C@@H](O)[C@H](O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7-/t16-,17-/m1/s1
InChI KeyXEBKSQSGNGRGDW-GJWDQICYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
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
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0605 +/- 0.00382 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.0605 +/- 0.0038 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0297 +/- 0.011 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00049 +/- 0.00044 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023415
KNApSAcK IDNot Available
Chemspider ID26324121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25320862
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE2047
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lecka-Czernik B, Moerman EJ, Grant DF, Lehmann JM, Manolagas SC, Jilka RL: Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation. Endocrinology. 2002 Jun;143(6):2376-84. [PubMed:12021203 ]
  2. Ha J, Dobretsov M, Kurten RC, Grant DF, Stimers JR: Effect of linoleic acid metabolites on Na(+)/K(+) pump current in N20.1 oligodendrocytes: role of membrane fluidity. Toxicol Appl Pharmacol. 2002 Jul 1;182(1):76-83. [PubMed:12127265 ]
  3. Thompson DA, Hammock BD: Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst. J Biosci. 2007 Mar;32(2):279-91. [PubMed:17435320 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.