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Record Information
Version4.0
Creation Date2006-08-14 01:55:43 UTC
Update Date2017-10-23 19:04:12 UTC
HMDB IDHMDB0004705
Secondary Accession Numbers
  • HMDB04705
Metabolite Identification
Common Name12,13-DHOME
Description12,13-DHOME is the epoxide hydrolase metabolite of the leukotoxin12,13-EpOME. 12,13-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 12,13-DiHOME specifically exerting toxicity. Both the EpOME and the DiHOME are shown to have neutrophil chemotactic activity. 12,13-DiHOME suppress 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. 12,13-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in human's tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. (PMID: 17435320 , 12021203 , 12127265 ).
Structure
Thumb
Synonyms
ValueSource
(9Z)-12,13-Dihydroxyoctadec-9-enoic acidChEBI
12,13-DHOAChEBI
12,13-Dihydroxy-9Z-octadecenoic acidChEBI
IsoleukotoxinChEBI
(9Z)-12,13-Dihydroxyoctadec-9-enoateGenerator
12,13-Dihydroxy-9Z-octadecenoateGenerator
12,13-DiHOMEHMDB
12,13-Dihydroxyoctadec-9(Z)-enoateHMDB
12,13-Dihydroxyoctadec-9(Z)-enoic acidHMDB
12,13-Hydroxyoctadec-9(Z)-enoateHMDB
12,13-Hydroxyoctadec-9(Z)-enoic acidHMDB
Chemical FormulaC18H34O4
Average Molecular Weight314.4602
Monoisotopic Molecular Weight314.245709576
IUPAC Name(9Z)-12,13-dihydroxyoctadec-9-enoic acid
Traditional Name(9Z)-12,13-dihydroxyoctadec-9-enoic acid
CAS Registry NumberNot Available
SMILES
CCCCCC(O)C(O)C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-
InChI KeyCQSLTKIXAJTQGA-FLIBITNWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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 Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.036 g/LALOGPS
logP5.2ALOGPS
logP4.32ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity90.43 m³·mol⁻¹ChemAxon
Polarizability37.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-7690000000-20547728320d3baec9e5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00vu-9213220000-cb8d7de99eff7f560193View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0192000000-d010555a4cfd00bda68dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-9860000000-491366f7ca08f7fe88d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y3-9310000000-41a866c27c5c89d2ba07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0059000000-fbc80cadc973f811e85bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-4593000000-5cc2f2c0a59cbfc01970View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9520000000-8a96365f22623f12f487View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00502 +/- 0.00019 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0166 (0.00440 - 0.0287) uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.00769 +/- 0.00059 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00582 +/- 0.003 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00062 +/- 0.00044 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
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 IDFDB023416
KNApSAcK IDNot Available
Chemspider ID8412123
KEGG Compound IDC14829
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10236635
PDB IDNot Available
ChEBI 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 ]