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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:09 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0010213
Secondary Accession Numbers
  • HMDB10213
Metabolite Identification
Common Name17-HDoHE
DescriptionDocosahexaenoic acid (DHA) is a omega-3 essential fatty acid that reduces the incidence and severity of a number of diseases. Recently, a novel series of DHA-derived lipid mediators with potent protective actions has been identified. In this study we demonstrate that dietary amplification of these DHA-derived products protects the liver from necroinflammatory injury. In vitro, supplementation of hepatocytes with DHA significantly reduced hydrogen peroxide-induced DNA damage, evaluated by the "comet assay," and oxidative stress, determined by measurement of malondialdehyde levels. In vivo, dietary supplementation of mice with DHA ameliorated carbon tetrachloride-induced necroinflammatory damage. In addition, hepatic cyclooxygenase-2 expression and PGE2 levels were significantly reduced in mice fed DHA-enriched diets. In these animals, increased hepatic formation of DHA-derived lipid mediators (i.e., 17S-hydroxy-DHA (17S-HDHA) and protectin D1) was detected by HPLC-gas chromatography/mass spectrometry analysis. Consistent with these findings, synthetic 17-HDHA abrogated genotoxic and oxidative damage in hepatocytes and decreased TNF-alpha release and 5-lipoxygenase expression in macrophages. In a transactivation assay, 17-HDHA acted in a concentration-dependent manner as a PPARgamma agonist. Taken together, these findings identify a potential role for DHA-derived products, specifically 17S-HDHA and protectin D1, in mediating the protective effects of dietary DHA in necroinflammatory liver injury. (PMID: 17056761 ). This fatty acyl belongs to the main class of docosanoids. (Lipid Maps).
Structure
Data?1582752797
Synonyms
ValueSource
(+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acidChEBI
17-HDHAChEBI
17-Hydroxy-dhaChEBI
(+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoateGenerator
(+/-)-17-hdoheHMDB
(4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoateHMDB
(4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoic acidHMDB
(e,Z,Z,Z,Z,Z)-17-Hydroxy-, 4,7,10,13,15,19-docosahexaenoateHMDB
(e,Z,Z,Z,Z,Z)-17-Hydroxy-, 4,7,10,13,15,19-docosahexaenoic acidHMDB
17-HdheHMDB
17-Hydroxy-4,7,10,13,15,19-docosahexaenoateHMDB
17-Hydroxy-4,7,10,13,15,19-docosahexaenoic acidHMDB
17-HydroxydocosahexaenoateHMDB
17-Hydroxydocosahexaenoic acidHMDB
17(R)HDoHEHMDB
17(S)-HDHAHMDB
(4Z,7Z,10Z,13Z,15E,19Z)-17-HydroxydocosahexaenoateHMDB
17-HDoHEChEBI
Chemical FormulaC22H32O3
Average Molecular Weight344.4877
Monoisotopic Molecular Weight344.23514489
IUPAC Name(4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoic acid
Traditional Name17-HDoHE
CAS Registry Number90780-52-2
SMILES
CC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C22H32O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19,21,23H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+
InChI KeySWTYBBUBEPPYCX-VIIQGJSXSA-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
  • 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
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 Solubility0.0012 g/LALOGPS
logP5.96ALOGPS
logP5.52ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity112.9 m³·mol⁻¹ChemAxon
Polarizability41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.43231661259
DarkChem[M-H]-194.21631661259
DeepCCS[M+H]+189.58930932474
DeepCCS[M-H]-187.23130932474
DeepCCS[M-2H]-220.39830932474
DeepCCS[M+Na]+195.68330932474
AllCCS[M+H]+192.932859911
AllCCS[M+H-H2O]+190.132859911
AllCCS[M+NH4]+195.532859911
AllCCS[M+Na]+196.332859911
AllCCS[M-H]-188.832859911
AllCCS[M+Na-2H]-190.732859911
AllCCS[M+HCOO]-193.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17-HDoHECC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O4591.9Standard polar33892256
17-HDoHECC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2542.4Standard non polar33892256
17-HDoHECC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2755.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17-HDoHE,1TMS,isomer #1CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C3015.8Semi standard non polar33892256
17-HDoHE,1TMS,isomer #2CC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C2856.2Semi standard non polar33892256
17-HDoHE,2TMS,isomer #1CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2900.2Semi standard non polar33892256
17-HDoHE,1TBDMS,isomer #1CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3246.9Semi standard non polar33892256
17-HDoHE,1TBDMS,isomer #2CC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C3100.7Semi standard non polar33892256
17-HDoHE,2TBDMS,isomer #1CC/C=C\CC(/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)C3375.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17-HDoHE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00os-7294000000-2a4b0084bba395e48c232017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-HDoHE GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9123400000-c3f28076bda49354c61e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-HDoHE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-HDoHE 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 - 17-HDoHE 10V, Positive-QTOFsplash10-004i-0019000000-2621fee5f670473525312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 20V, Positive-QTOFsplash10-05pk-4294000000-788cbda5c1d54e3e38732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 40V, Positive-QTOFsplash10-000l-9750000000-84f60ba92674f1644cc42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 10V, Negative-QTOFsplash10-0006-0019000000-83f7ecff978572fcffd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 20V, Negative-QTOFsplash10-004l-2049000000-c6c5596e50dc71d09cb52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 40V, Negative-QTOFsplash10-0a4l-9130000000-d2576e5d4bf1ca8ac6f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 10V, Positive-QTOFsplash10-004i-0239000000-454a49281e853960a9ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 20V, Positive-QTOFsplash10-06vj-0595000000-f50e2ae05dbadfc166ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 40V, Positive-QTOFsplash10-067l-5910000000-01d22e420136f2171ba42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 10V, Negative-QTOFsplash10-002f-0019000000-717f7e839f15c9a100002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 20V, Negative-QTOFsplash10-004i-1139000000-36418d1147855544ba3d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-HDoHE 40V, Negative-QTOFsplash10-006x-9060000000-7beceef62592685d7c592021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000194 +/- 0.000007 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000773 +/- 0.00064 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 IDFDB027368
KNApSAcK IDNot Available
Chemspider ID4943608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439179
PDB IDNot Available
ChEBI ID72637
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. Levy BD, Kohli P, Gotlinger K, Haworth O, Hong S, Kazani S, Israel E, Haley KJ, Serhan CN: Protectin D1 is generated in asthma and dampens airway inflammation and hyperresponsiveness. J Immunol. 2007 Jan 1;178(1):496-502. [PubMed:17182589 ]
  2. Gonzalez-Periz A, Planaguma A, Gronert K, Miquel R, Lopez-Parra M, Titos E, Horrillo R, Ferre N, Deulofeu R, Arroyo V, Rodes J, Claria J: Docosahexaenoic acid (DHA) blunts liver injury by conversion to protective lipid mediators: protectin D1 and 17S-hydroxy-DHA. FASEB J. 2006 Dec;20(14):2537-9. Epub 2006 Oct 20. [PubMed:17056761 ]
  3. Miller C, Yamaguchi RY, Ziboh VA: Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids. Lipids. 1989 Dec;24(12):998-1003. [PubMed:2559281 ]