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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:10 UTC
Update Date2021-09-14 15:44:19 UTC
HMDB IDHMDB0010214
Secondary Accession Numbers
  • HMDB10214
Metabolite Identification
Common Name19,20-DiHDPA
Description19,20-DiHDPA is one of the major metabolites produced when Docosahexaenoic acid (DHA) is incubated with NADPH-supplemented rat liver microsomes. Docosahexaenoic acid (DHA) is an essential fatty acid and the most abundant omega-3 fatty acid in neural tissues, especially in the retina and brain. DHA is also slowly metabolized by monkey seminal vesicles to 19,20-DiHDPA. The route of production likely proceeds through cytochrome P450-catalyzed epoxidation at the omega-3 double bond, followed by conversion to the vicinal diols by epoxide hydrolase. (PMID: 1742320 ).
Structure
Data?1582752798
Synonyms
ValueSource
19,20-DiHDoPEChEBI
19,20-DiHDPEChEBI
19,20-Dihydroxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acidChEBI
19,20-Dihydroxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoateGenerator
(+/-)19,20-dihdopeHMDB
19,20-DihydroxydocosapentaenoateHMDB
19,20-Dihydroxydocosapentaenoic acidHMDB
19,20-DiHDPAMeSH
Chemical FormulaC22H34O4
Average Molecular Weight362.503
Monoisotopic Molecular Weight362.245709576
IUPAC Name(4Z,7Z,10Z,13Z,16Z)-19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid
Traditional Name(4Z,7Z,10Z,13Z,16Z)-19,20-dihydroxydocosa-4,7,10,13,16-pentaenoic acid
CAS Registry NumberNot Available
SMILES
CCC(O)C(O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C22H34O4/c1-2-20(23)21(24)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(25)26/h3-4,7-10,13-16,20-21,23-24H,2,5-6,11-12,17-19H2,1H3,(H,25,26)/b4-3-,9-7-,10-8-,15-13-,16-14-
InChI KeyFFXKPSNQCPNORO-MBYQGORISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very 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

Source

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 Solubility0.0064 g/LALOGPS
logP5.22ALOGPS
logP4.65ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity113.3 m³·mol⁻¹ChemAxon
Polarizability41.45 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]+202.09331661259
DarkChem[M-H]-198.15731661259
DeepCCS[M+H]+191.53630932474
DeepCCS[M-H]-189.17830932474
DeepCCS[M-2H]-223.12430932474
DeepCCS[M+Na]+198.35130932474
AllCCS[M+H]+198.632859911
AllCCS[M+H-H2O]+195.932859911
AllCCS[M+NH4]+201.032859911
AllCCS[M+Na]+201.732859911
AllCCS[M-H]-193.932859911
AllCCS[M+Na-2H]-196.232859911
AllCCS[M+HCOO]-198.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
19,20-DiHDPACCC(O)C(O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O4605.5Standard polar33892256
19,20-DiHDPACCC(O)C(O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2497.1Standard non polar33892256
19,20-DiHDPACCC(O)C(O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2882.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
19,20-DiHDPA,1TMS,isomer #1CCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O3114.8Semi standard non polar33892256
19,20-DiHDPA,1TMS,isomer #2CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C3120.8Semi standard non polar33892256
19,20-DiHDPA,1TMS,isomer #3CCC(O)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C2949.1Semi standard non polar33892256
19,20-DiHDPA,2TMS,isomer #1CCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C3032.6Semi standard non polar33892256
19,20-DiHDPA,2TMS,isomer #2CCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C2961.6Semi standard non polar33892256
19,20-DiHDPA,2TMS,isomer #3CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2951.0Semi standard non polar33892256
19,20-DiHDPA,3TMS,isomer #1CCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2931.0Semi standard non polar33892256
19,20-DiHDPA,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O3372.5Semi standard non polar33892256
19,20-DiHDPA,1TBDMS,isomer #2CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3368.8Semi standard non polar33892256
19,20-DiHDPA,1TBDMS,isomer #3CCC(O)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C3204.5Semi standard non polar33892256
19,20-DiHDPA,2TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3483.0Semi standard non polar33892256
19,20-DiHDPA,2TBDMS,isomer #2CCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C3434.5Semi standard non polar33892256
19,20-DiHDPA,2TBDMS,isomer #3CCC(O)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3428.8Semi standard non polar33892256
19,20-DiHDPA,3TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3639.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 19,20-DiHDPA GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-8249000000-7e742d8fd56a33203bdd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19,20-DiHDPA GC-MS (3 TMS) - 70eV, Positivesplash10-03di-3231490000-8e326e4de1b06da54e6a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19,20-DiHDPA 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 - 19,20-DiHDPA 10V, Positive-QTOFsplash10-0002-0019000000-29bb8e624c9a8d7dd2862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Positive-QTOFsplash10-056s-2094000000-1749ffa613a37fc785e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Positive-QTOFsplash10-01r6-6390000000-fc91fa813229e0592fca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 10V, Negative-QTOFsplash10-03di-0009000000-3d99a1a7ed4531ad8cf62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Negative-QTOFsplash10-0btc-4039000000-b0d4491c9320a09cc67c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Negative-QTOFsplash10-0a4i-9011000000-fc9f8b3372dc20645e382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 10V, Negative-QTOFsplash10-03di-0009000000-70804a01cf218984bcbd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Negative-QTOFsplash10-0a4i-6049000000-bcac3b983044ec8097212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Negative-QTOFsplash10-052r-9073000000-cc0870715c7efeb917a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 10V, Positive-QTOFsplash10-002b-0029000000-11ea7ffba8e57db6a3732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 20V, Positive-QTOFsplash10-004j-2369000000-9d469005a5dce85aa5302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19,20-DiHDPA 40V, Positive-QTOFsplash10-0159-5920000000-a4e85897e8df32a222872021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00123 +/- 0.000389 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00664 +/- 0.000469 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.000805 +/- 0.00042 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 IDFDB027369
KNApSAcK IDNot Available
Chemspider ID17220827
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061148
PDB IDNot Available
ChEBI ID72657
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 References
  1. Oliw EH, Sprecher HW: Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: isolation and biosynthesis of omega-3 epoxides. Biochim Biophys Acta. 1991 Nov 27;1086(3):287-94. [PubMed:1742320 ]