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Record Information
Version3.6
Creation Date2006-08-14 01:55:43 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04705
Secondary Accession NumbersNone
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-DHOMEChEBI
12,13-Dihydroxy-9Z-octadecenoic acidChEBI
IsoleukotoxinChEBI
(9Z)-12,13-Dihydroxyoctadec-9-enoateGenerator
(Z)-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 KeyInChIKey=CQSLTKIXAJTQGA-FLIBITNWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity90.43 m3·mol-1ChemAxon
Polarizability37.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB04705
Metagene LinkHMDB04705
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. [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. [12127265 ]
  3. Thompson DA, Hammock BD: Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst. J Biosci. 2007 Mar;32(2):279-91. [17435320 ]