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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:32 UTC
Update Date2022-03-07 02:53:10 UTC
HMDB IDHMDB0031923
Secondary Accession Numbers
  • HMDB31923
Metabolite Identification
Common Name10,20-Dihydroxyeicosanoic acid
Description10,20-Dihydroxyeicosanoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Based on a literature review a small amount of articles have been published on 10,20-Dihydroxyeicosanoic acid.
Structure
Data?1563862192
Synonyms
ValueSource
10,20-DihydroxyeicosanoateGenerator
10,20-DihydroxyicosanoateHMDB
Chemical FormulaC20H40O4
Average Molecular Weight344.5292
Monoisotopic Molecular Weight344.292659768
IUPAC Name10,20-dihydroxyicosanoic acid
Traditional Name10,20-dihydroxyicosanoic acid
CAS Registry Number120727-26-6
SMILES
OCCCCCCCCCCC(O)CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H40O4/c21-18-14-10-6-2-1-3-7-11-15-19(22)16-12-8-4-5-9-13-17-20(23)24/h19,21-22H,1-18H2,(H,23,24)
InChI KeyRIIQXYZWFWMFSB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot 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 Solubility0.0048 g/LALOGPS
logP6.06ALOGPS
logP5.21ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity99.09 m³·mol⁻¹ChemAxon
Polarizability44.79 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]+188.74131661259
DarkChem[M-H]-187.69231661259
DeepCCS[M+H]+188.96230932474
DeepCCS[M-H]-184.94230932474
DeepCCS[M-2H]-221.57630932474
DeepCCS[M+Na]+197.77730932474
AllCCS[M+H]+195.332859911
AllCCS[M+H-H2O]+192.832859911
AllCCS[M+NH4]+197.632859911
AllCCS[M+Na]+198.332859911
AllCCS[M-H]-189.832859911
AllCCS[M+Na-2H]-191.132859911
AllCCS[M+HCOO]-192.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
10,20-Dihydroxyeicosanoic acidOCCCCCCCCCCC(O)CCCCCCCCC(O)=O4035.3Standard polar33892256
10,20-Dihydroxyeicosanoic acidOCCCCCCCCCCC(O)CCCCCCCCC(O)=O2601.6Standard non polar33892256
10,20-Dihydroxyeicosanoic acidOCCCCCCCCCCC(O)CCCCCCCCC(O)=O2850.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
10,20-Dihydroxyeicosanoic acid,1TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCC(O)CCCCCCCCC(=O)O2938.9Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,1TMS,isomer #2C[Si](C)(C)OC(CCCCCCCCCCO)CCCCCCCCC(=O)O2893.0Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCCC(O)CCCCCCCCCCO2871.9Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,2TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCC(CCCCCCCCC(=O)O)O[Si](C)(C)C2945.3Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,2TMS,isomer #2C[Si](C)(C)OCCCCCCCCCCC(O)CCCCCCCCC(=O)O[Si](C)(C)C2937.1Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCCC(CCCCCCCCCCO)O[Si](C)(C)C2865.7Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,3TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCC(CCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2934.5Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCC(O)CCCCCCCCC(=O)O3163.7Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CCCCCCCCCCO)CCCCCCCCC(=O)O3151.8Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(O)CCCCCCCCCCO3129.2Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCC(CCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3458.9Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCCCCCCCC(O)CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3449.3Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(CCCCCCCCCCO)O[Si](C)(C)C(C)(C)C3403.6Semi standard non polar33892256
10,20-Dihydroxyeicosanoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCC(CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3692.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 10,20-Dihydroxyeicosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-3952000000-80ce5c4109371106319e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10,20-Dihydroxyeicosanoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00aj-9728350000-1c421b1973260ed81e872017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10,20-Dihydroxyeicosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10,20-Dihydroxyeicosanoic acid 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 - 10,20-Dihydroxyeicosanoic acid 10V, Positive-QTOFsplash10-056s-0019000000-a3496645fead2dc080932016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 20V, Positive-QTOFsplash10-0a7j-1589000000-ac60aa850c3057e7a2122016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 40V, Positive-QTOFsplash10-02u4-8980000000-0558ac9dbb0e9afaee982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 10V, Negative-QTOFsplash10-0006-0019000000-5d6a3abaf9fe3e2d9d392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 20V, Negative-QTOFsplash10-002g-1259000000-c84359b476c21381fe4b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 40V, Negative-QTOFsplash10-0a4l-9520000000-79baf4d9d2f48de0b88e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 10V, Negative-QTOFsplash10-0006-0009000000-b23c3fbaf8f9c8cf36352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 20V, Negative-QTOFsplash10-004l-1009000000-248bd6de9e27de2c1fe62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 40V, Negative-QTOFsplash10-054o-8194000000-fc948cf96261ab8b75a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 10V, Positive-QTOFsplash10-056r-0019000000-73356ad36187c674fd532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 20V, Positive-QTOFsplash10-0a6r-4149000000-cc08ccd796b056ed52ce2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10,20-Dihydroxyeicosanoic acid 40V, Positive-QTOFsplash10-0a4l-9100000000-9b29536d612908477ce92021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008611
KNApSAcK IDC00056634
Chemspider ID35013414
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14259007
PDB IDNot Available
ChEBI ID172568
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.