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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-05-01 17:30:02 UTC
Update Date2021-09-14 15:47:33 UTC
HMDB IDHMDB0060047
Secondary Accession Numbers
  • HMDB60047
Metabolite Identification
Common Name16-HDoHE
Description16-HDoHE 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. 16-HDoHE is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866009
Synonyms
ValueSource
(4Z,7Z,10Z,13Z,17Z,19Z)-16-Hydroxydocosa-4,7,10,13,17,19-hexaenoateGenerator
Chemical FormulaC22H32O3
Average Molecular Weight344.4877
Monoisotopic Molecular Weight344.23514489
IUPAC Name(4Z,7Z,10Z,13Z,17Z,19Z)-16-hydroxydocosa-4,7,10,13,17,19-hexaenoic acid
Traditional Name(4Z,7Z,10Z,13Z,17Z,19Z)-16-hydroxydocosa-4,7,10,13,17,19-hexaenoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C=C\C(O)C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C22H32O3/c1-2-3-4-15-18-21(23)19-16-13-11-9-7-5-6-8-10-12-14-17-20-22(24)25/h3-4,6-9,12-16,18,21,23H,2,5,10-11,17,19-20H2,1H3,(H,24,25)/b4-3-,8-6-,9-7-,14-12-,16-13-,18-15-
InChI KeyCSXQXWHAGLIFIH-OMFYHICESA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP5.95ALOGPS
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
Polarizability41.33 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]+194.12831661259
DarkChem[M-H]-194.16131661259
DeepCCS[M+H]+189.9630932474
DeepCCS[M-H]-187.60230932474
DeepCCS[M-2H]-220.79930932474
DeepCCS[M+Na]+196.05330932474
AllCCS[M+H]+193.032859911
AllCCS[M+H-H2O]+190.132859911
AllCCS[M+NH4]+195.632859911
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
16-HDoHECC\C=C/C=C\C(O)C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O4628.9Standard polar33892256
16-HDoHECC\C=C/C=C\C(O)C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2546.9Standard non polar33892256
16-HDoHECC\C=C/C=C\C(O)C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2754.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16-HDoHE,1TMS,isomer #1CC/C=C\C=C/C(C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C3029.9Semi standard non polar33892256
16-HDoHE,1TMS,isomer #2CC/C=C\C=C/C(O)C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C2864.5Semi standard non polar33892256
16-HDoHE,2TMS,isomer #1CC/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)C2906.1Semi standard non polar33892256
16-HDoHE,1TBDMS,isomer #1CC/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)C3258.6Semi standard non polar33892256
16-HDoHE,1TBDMS,isomer #2CC/C=C\C=C/C(O)C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C3103.1Semi standard non polar33892256
16-HDoHE,2TBDMS,isomer #1CC/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)C3381.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16-HDoHE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-6795000000-2c46124efdecfcac60c42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-HDoHE GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9325500000-a6c663e1663bdf2104e12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-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 - 16-HDoHE 10V, Positive-QTOFsplash10-004i-0019000000-959be37a5d921aa5b1eb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 20V, Positive-QTOFsplash10-069s-6295000000-57d6eb569984dcc63c462017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 40V, Positive-QTOFsplash10-00rl-9650000000-2399fd5f270ca73d842b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 10V, Negative-QTOFsplash10-0006-0019000000-e0078d04ca23ffe798902017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 20V, Negative-QTOFsplash10-004l-1049000000-0c470f357ec826fd3a802017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 40V, Negative-QTOFsplash10-0a4l-9240000000-6810229086dc7cff6b6c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 10V, Positive-QTOFsplash10-004i-0029000000-0bf1745465be20fbdbaa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 20V, Positive-QTOFsplash10-004i-5889000000-b6c8c5394185449dafd22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 40V, Positive-QTOFsplash10-069u-8910000000-7f2cbfb4b54dfc9e24c12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 10V, Negative-QTOFsplash10-002f-0009000000-ec94566c6f30794046fd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 20V, Negative-QTOFsplash10-004l-1039000000-83668c555a8e2a48a19e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-HDoHE 40V, Negative-QTOFsplash10-00r7-9120000000-2fd53bb9280677d021572021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000202 +/- 0.000041 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769806
PDB IDNot Available
ChEBI IDNot Available
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. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.