Record Information
Version1.0
Creation date2011-09-21 00:29:37 UTC
Update date2015-07-21 06:57:42 UTC
Primary IDFDB023415
Secondary Accession Numbers
  • FDB008339
Chemical Information
FooDB Name9,10-DHOME
Description9,10-DHOME is a derivative of linoleic acid diol that have 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-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 9,10-DiHOME specifically exerting toxicity. Both the 9,10-EpOME and the 9,10-DiHOME are shown to have neutrophil chemotactic activity. 9,10-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. (PMID: 12021203, 12127265, 17435320) [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP5.18ALOGPS
logP4.32ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
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
Polarizability39.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H34O4
IUPAC name(12E)-9,10-dihydroxyoctadec-12-enoic acid
InChI IdentifierInChI=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+
InChI KeyXEBKSQSGNGRGDW-JXMROGBWSA-N
Isomeric SMILESCCCCC\C=C\CC(O)C(O)CCCCCCCC(O)=O
Average Molecular Weight314.4602
Monoisotopic Molecular Weight314.245709576
Classification
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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(9xi,10xi,12xi)-9,10-Dihydroxy-12-octadecenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dm-4920000000-f74ccedf3267a9ce3bf4Spectrum
Predicted GC-MS(9xi,10xi,12xi)-9,10-Dihydroxy-12-octadecenoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-016r-9212320000-21108e48262d95903434Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-0009000000-77cc7fdc656761081db32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-0009000000-ffc80d839bc1257f5b052017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-0009000000-4336a635801eac094dc02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-0049000000-1d9acdeca87439e569362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0w29-0194000000-42d4a62f1bd0b85ad15f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0291000000-512176d5b5bef61ddbf12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0490000000-5c7529e26b7379daa0fc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0890000000-635a557f3e5b47dbbd812017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0umi-0950000000-692dd4f4e4e822232b562017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0194000000-5d744841b3bda349fe912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9850000000-d429bf1cd44daab92c372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9200000000-fb179fe5bea2b522777e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0239000000-c98a309c401ce8dca7fa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1942000000-60c6d5c90dcf298376772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-a545c3829c9a22779f4d2016-08-03View Spectrum
NMRNot Available
ChemSpider ID8142232
ChEMBL IDNot Available
KEGG Compound IDC14828
Pubchem Compound ID9966640
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04704
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
AnatidaeExpected but not quantifiedNot AvailableHMDB
BeefaloExpected but not quantifiedNot AvailableHMDB
BisonExpected but not quantifiedNot AvailableHMDB
BuffaloExpected but not quantifiedNot AvailableHMDB
Cattle (Beef, Veal)Expected but not quantifiedNot AvailableHMDB
ChickenExpected but not quantifiedNot AvailableHMDB
Columbidae (Dove, Pigeon)Expected but not quantifiedNot AvailableHMDB
DeerExpected but not quantifiedNot AvailableHMDB
Domestic goatExpected but not quantifiedNot AvailableHMDB
Domestic pigExpected but not quantifiedNot AvailableHMDB
Showing 1 to 10 of 29 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference