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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:54:57 UTC
Update Date2021-09-14 15:46:46 UTC
HMDB IDHMDB0010201
Secondary Accession Numbers
  • HMDB10201
Metabolite Identification
Common Name12,13-DiHODE
Description12,13-DiHODE, also known as a-12,13-dihode, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 12,13-dihode is considered to be an octadecanoid. Based on a literature review very few articles have been published on 12,13-DiHODE.
Structure
Data?1582752796
Synonyms
ValueSource
(+/-)-12,13-dihydroxy-9Z,15Z-octadecadienoateHMDB
(+/-)-12,13-dihydroxy-9Z,15Z-octadecadienoic acidHMDB
(9Z,15Z)-12,13-Dihydroxyoctadeca-9,15-dienoateHMDB
(9Z,15Z)-12,13-Dihydroxyoctadeca-9,15-dienoic acidHMDB
a-12,13-DiHODEHMDB
alpha-12,13-DiHODEHMDB
Α-12,13-dihodeHMDB
Chemical FormulaC18H32O4
Average Molecular Weight312.4443
Monoisotopic Molecular Weight312.230059512
IUPAC Name(9Z,15Z)-12,13-dihydroxyoctadeca-9,15-dienoic acid
Traditional Name(9Z,15Z)-12,13-dihydroxyoctadeca-9,15-dienoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/CC(O)C(O)C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h3,8,10-11,16-17,19-20H,2,4-7,9,12-15H2,1H3,(H,21,22)/b10-3-,11-8-
InChI KeyRGRKFKRAFZJQMS-OOHFSOINSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 Solubility0.044 g/LALOGPS
logP5.03ALOGPS
logP3.96ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity91.55 m³·mol⁻¹ChemAxon
Polarizability37.31 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
DarkChem[M+H]+183.75331661259
DarkChem[M-H]-179.16131661259
DeepCCS[M+H]+181.31130932474
DeepCCS[M-H]-178.95330932474
DeepCCS[M-2H]-211.8430932474
DeepCCS[M+Na]+187.40430932474
AllCCS[M+H]+184.932859911
AllCCS[M+H-H2O]+182.132859911
AllCCS[M+NH4]+187.632859911
AllCCS[M+Na]+188.432859911
AllCCS[M-H]-182.432859911
AllCCS[M+Na-2H]-184.032859911
AllCCS[M+HCOO]-185.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12,13-DiHODECC\C=C/CC(O)C(O)C\C=C/CCCCCCCC(O)=O3986.7Standard polar33892256
12,13-DiHODECC\C=C/CC(O)C(O)C\C=C/CCCCCCCC(O)=O2287.9Standard non polar33892256
12,13-DiHODECC\C=C/CC(O)C(O)C\C=C/CCCCCCCC(O)=O2449.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12,13-DiHODE,1TMS,isomer #1CC/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\CCCCCCCC(=O)O2605.5Semi standard non polar33892256
12,13-DiHODE,1TMS,isomer #2CC/C=C\CC(O)C(C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C2615.8Semi standard non polar33892256
12,13-DiHODE,1TMS,isomer #3CC/C=C\CC(O)C(O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2570.5Semi standard non polar33892256
12,13-DiHODE,2TMS,isomer #1CC/C=C\CC(O[Si](C)(C)C)C(C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C2631.0Semi standard non polar33892256
12,13-DiHODE,2TMS,isomer #2CC/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2572.6Semi standard non polar33892256
12,13-DiHODE,2TMS,isomer #3CC/C=C\CC(O)C(C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2570.7Semi standard non polar33892256
12,13-DiHODE,3TMS,isomer #1CC/C=C\CC(O[Si](C)(C)C)C(C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2577.5Semi standard non polar33892256
12,13-DiHODE,1TBDMS,isomer #1CC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\CCCCCCCC(=O)O2854.6Semi standard non polar33892256
12,13-DiHODE,1TBDMS,isomer #2CC/C=C\CC(O)C(C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2863.7Semi standard non polar33892256
12,13-DiHODE,1TBDMS,isomer #3CC/C=C\CC(O)C(O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2804.8Semi standard non polar33892256
12,13-DiHODE,2TBDMS,isomer #1CC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3075.6Semi standard non polar33892256
12,13-DiHODE,2TBDMS,isomer #2CC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3027.2Semi standard non polar33892256
12,13-DiHODE,2TBDMS,isomer #3CC/C=C\CC(O)C(C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3030.5Semi standard non polar33892256
12,13-DiHODE,3TBDMS,isomer #1CC/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3242.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12,13-DiHODE GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-7890000000-1f593c78df5e56f75e4e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12,13-DiHODE GC-MS (3 TMS) - 70eV, Positivesplash10-076r-9442540000-37c208df287828872c0f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12,13-DiHODE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12,13-DiHODE 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-DiHODE 10V, Positive-QTOFsplash10-0002-0192000000-915dc887d4c23876f26f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 20V, Positive-QTOFsplash10-014i-9850000000-f06b31649d76e0fba7a02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 40V, Positive-QTOFsplash10-014r-9500000000-195d408f338563596c182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 10V, Negative-QTOFsplash10-03di-0059000000-c6200bd4e6b560b8596e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 20V, Negative-QTOFsplash10-03xv-5493000000-64d8c2022162e04a6aa52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 40V, Negative-QTOFsplash10-0a4j-9420000000-156c88934784a3a16e142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 10V, Negative-QTOFsplash10-03di-0019000000-b31bbe8a661ec53c1e472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 20V, Negative-QTOFsplash10-03dl-2794000000-49f385d42109b303327a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 40V, Negative-QTOFsplash10-0002-9410000000-707d29171f87feaf7a5b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 10V, Positive-QTOFsplash10-002b-2692000000-9ea2c15f6427c5b77e372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 20V, Positive-QTOFsplash10-00os-9630000000-1c262d6dde0856e55e642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12,13-DiHODE 40V, Positive-QTOFsplash10-067l-9200000000-f75a6128b01c3340419a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.0002 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000219 +/- 0.00012 uMAdult (>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 IDFDB027356
KNApSAcK IDNot Available
Chemspider ID17220750
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061067
PDB IDNot Available
ChEBI ID88461
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available