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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:54:13 UTC
Update Date2021-09-14 15:43:43 UTC
HMDB IDHMDB0060096
Secondary Accession Numbers
  • HMDB60096
Metabolite Identification
Common Name5,12,18R-TriHEPE
Description5,12,18R-TriHEPE belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. 5,12,18R-TriHEPE is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866015
SynonymsNot Available
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5R,6E,8Z,10E,12S,14Z,16E,18R)-5,12,18-trihydroxyicosa-6,8,10,14,16-pentaenoic acid
Traditional Name(5R,6E,8Z,10E,12S,14Z,16E,18R)-5,12,18-trihydroxyicosa-6,8,10,14,16-pentaenoic acid
CAS Registry NumberNot Available
SMILES
CC[C@@H](O)\C=C\C=C/C[C@H](O)\C=C\C=C/C=C/[C@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O5/c1-2-17(21)11-8-5-9-14-18(22)12-6-3-4-7-13-19(23)15-10-16-20(24)25/h3-9,11-13,17-19,21-23H,2,10,14-16H2,1H3,(H,24,25)/b4-3-,9-5-,11-8+,12-6+,13-7+/t17-,18-,19+/m1/s1
InChI KeyAOPOCGPBAIARAV-OSEJDTMESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosapentaenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosapentaenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP10(4.24) g/LALOGPS
logP10(2.53) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity105.62 m³·mol⁻¹ChemAxon
Polarizability39.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.96831661259
DarkChem[M-H]-190.81931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,12,18R-TriHEPE,1TMS,#1CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C3226.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TMS,#2CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C3238.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TMS,#3CC[C@@H](O)/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C3237.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TMS,#4CC[C@@H](O)/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C3150.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TMS,#1CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3269.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TMS,#2CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3263.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TMS,#3CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3178.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TMS,#4CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3270.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TMS,#5CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3187.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TMS,#6CC[C@@H](O)/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3188.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TMS,#1CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3284.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TMS,#2CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3217.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TMS,#3CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3209.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TMS,#4CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3207.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,4TMS,#1CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3244.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TBDMS,#1CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3474.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TBDMS,#2CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3487.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TBDMS,#3CC[C@@H](O)/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3475.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,1TBDMS,#4CC[C@@H](O)/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3403.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TBDMS,#1CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3758.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TBDMS,#2CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3746.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TBDMS,#3CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3683.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TBDMS,#4CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3749.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TBDMS,#5CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3688.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,2TBDMS,#6CC[C@@H](O)/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3677.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TBDMS,#1CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4035.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TBDMS,#2CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3988.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TBDMS,#3CC[C@H](/C=C/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3978.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,3TBDMS,#4CC[C@@H](O)/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3970.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5,12,18R-TriHEPE,4TBDMS,#1CC[C@H](/C=C/C=C\C[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4238.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 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 Compound131769819
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. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  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.