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Record Information
Version2.0
Created at2022-09-11 14:38:38 UTC
Updated at2022-09-11 14:38:38 UTC
NP-MRD IDNP0315820
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5z,8z,11z,14z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
Description17,18-EpETE, also known as 17,18-eeq or 17R,18S-epete, 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. Thus, 17,18-epete is considered to be an eicosanoid lipid molecule. An EpETE obtained by formal epoxidation of the 17,18-double bond of all-cis-5,8,11,14,17-icosapentaenoic acid. (5z,8z,11z,14z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid is found in Pseudo-nitzschia multistriata. 17,18-EpETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
Chemical FormulaC20H30O3
Average Mass318.4504 Da
Monoisotopic Mass318.21949 Da
IUPAC Name(5Z,8Z,11Z,14Z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
Traditional Name(5Z,8Z,11Z,14Z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b5-3-,8-6-,11-9-,14-12-
InChI KeyGPQVVJQEBXAKBJ-JPURVOHMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pseudo-nitzschia multistriataLOTUS Database
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
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.8ALOGPS
logP5.29ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.47 m³·mol⁻¹ChemAxon
Polarizability37.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0010212
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027367
KNApSAcK IDNot Available
Chemspider ID17220772
KEGG Compound IDC13843
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061089
PDB IDNot Available
ChEBI ID72853
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]