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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 01:55:43 UTC
Update Date2022-09-22 17:43:53 UTC
HMDB IDHMDB0004705
Secondary Accession Numbers
  • HMDB04705
Metabolite Identification
Common Name12,13-DHOME
Description12,13-DHOME (CAS: 263399-35-5), also known as 12,13-dihydroxy-9-octadecenoic acid or 12,13-DiHOME, is the epoxide hydrolase metabolite of the leukotoxin 12,13-EpOME. 12,13-EpOME acts as a protoxin, with the corresponding epoxide hydrolase 12,13-DHOME specifically exerting toxicity. Both the EpOME and the DHOME are shown to have neutrophil chemotactic activity. 12,13-DHOME 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 the linoleic acid diol that has been reported to be toxic in human 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
Data?1582752313
Synonyms
ValueSource
12,13-DihydroxyoleateHMDB
(-)-Threo-12,13-dihydroxyoleic acidHMDB
(9Z)-12,13-Dihydroxy-9-octadecenoic acidHMDB
(9Z,12S,13S)-12,13-Dihydroxy-9-octadecenoic acidHMDB
12,13-DiHOMEHMDB
FA(18:1(9Z,12S,13S))HMDB
FA(18:1(9Z,12S-OH,13S-OH))HMDB
12,13-DHOMEHMDB
Chemical FormulaC18H34O4
Average Molecular Weight314.466
Monoisotopic Molecular Weight314.245709575
IUPAC Name(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid
Traditional Name(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid
CAS Registry Number7293-40-5
SMILES
CCCCC[C@H](O)[C@@H](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-/t16-,17-/m0/s1
InChI KeyCQSLTKIXAJTQGA-BTDPBSJTSA-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 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
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
Polarizability38.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+188.96930932474
DeepCCS[M-H]-186.61130932474
DeepCCS[M-2H]-219.49730932474
DeepCCS[M+Na]+195.06230932474
AllCCS[M+H]+186.732859911
AllCCS[M+H-H2O]+183.932859911
AllCCS[M+NH4]+189.332859911
AllCCS[M+Na]+190.132859911
AllCCS[M-H]-183.332859911
AllCCS[M+Na-2H]-184.932859911
AllCCS[M+HCOO]-186.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12,13-DHOMECCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O3886.1Standard polar33892256
12,13-DHOMECCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O2371.2Standard non polar33892256
12,13-DHOMECCCCC[C@H](O)[C@@H](O)C\C=C/CCCCCCCC(O)=O2508.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12,13-DHOME,1TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O2513.5Semi standard non polar33892256
12,13-DHOME,1TMS,isomer #2CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C2529.7Semi standard non polar33892256
12,13-DHOME,1TMS,isomer #3CCCCC[C@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2537.0Semi standard non polar33892256
12,13-DHOME,2TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C2532.7Semi standard non polar33892256
12,13-DHOME,2TMS,isomer #2CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2545.9Semi standard non polar33892256
12,13-DHOME,2TMS,isomer #3CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2554.9Semi standard non polar33892256
12,13-DHOME,3TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2542.8Semi standard non polar33892256
12,13-DHOME,1TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O2754.6Semi standard non polar33892256
12,13-DHOME,1TBDMS,isomer #2CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2757.4Semi standard non polar33892256
12,13-DHOME,1TBDMS,isomer #3CCCCC[C@H](O)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2779.6Semi standard non polar33892256
12,13-DHOME,2TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3027.1Semi standard non polar33892256
12,13-DHOME,2TBDMS,isomer #2CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3020.1Semi standard non polar33892256
12,13-DHOME,2TBDMS,isomer #3CCCCC[C@H](O)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3038.6Semi standard non polar33892256
12,13-DHOME,3TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3276.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12,13-DHOME GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DHOME 10V, Negative-QTOFsplash10-03di-0119000000-4c868de0f3de6c07f5492021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DHOME 20V, Negative-QTOFsplash10-03dj-3985000000-11f56948c3f5b836b8502021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DHOME 40V, Negative-QTOFsplash10-0002-9510000000-44b29fc1dc61e8abffec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DHOME 10V, Positive-QTOFsplash10-00mk-0492000000-08dc8525353e9939cf8d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DHOME 20V, Positive-QTOFsplash10-00pj-9650000000-e6462e60e7ab620364b52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DHOME 40V, Positive-QTOFsplash10-0apl-9200000000-bd2c48bf7ac9bd897d4a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023416
KNApSAcK IDNot Available
Chemspider ID26324122
KEGG Compound IDC14829
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25320870
PDB IDNot Available
ChEBI ID72665
Food Biomarker OntologyNot Available
VMH IDCE2049
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 ]