You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2008-09-15 09:55:10 UTC
Update Date2017-10-23 19:05:36 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
Thumb
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
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
DescriptionThis compound belongs to the class of chemical entities known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

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 Solubility0.0065 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-8249000000-7e742d8fd56a33203bddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-3231490000-8e326e4de1b06da54e6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0019000000-29bb8e624c9a8d7dd286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-2094000000-1749ffa613a37fc785e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r6-6390000000-fc91fa813229e0592fcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-3d99a1a7ed4531ad8cf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btc-4039000000-b0d4491c9320a09cc67cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9011000000-fc9f8b3372dc20645e38View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]