Record Information
Version1.0
Creation date2011-09-21 00:29:24 UTC
Update date2015-07-21 06:57:41 UTC
Primary IDFDB023403
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name11,12,15-THETA
Description11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). 11,12,15-THETA is an endothelium-derived relaxing factor. Acetylcholine stimulates AA release from membrane phospholipids of vascular endothelial cells (ECs). AA is released from phosphatidylcholine (PC) and phosphatidylethanolamine (PE) by phospholipase A2 (PLA2), or from phosphatidylinositol (PI) by phospholipase C (PLC) pathway. The diacylglycerol (DAG) lipase can convert DAG into 2-arachidonoylglycerol from which free AA can be released by monoacylglycerol (MAG) lipase or fatty acid amidohydrolase (FAAH). 11,12,15-THETA mediates the acetylcholine-induced vaso-relaxation, via activation of the K+ channels to hyperpolarize the smooth muscle membrane and induce relaxation. (PMID: 12907422, 16024567, 15388505, 14622984) [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoateGenerator
(5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoic acidKegg
(5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoateGenerator
(5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoic acidKegg
11,12,15-TriHETREHMDB
11,12,15-Trihydroxyicosatrienoatehmdb
11,12,15-Trihydroxyicosatrienoic acidhmdb
11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoatehmdb
11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP4.46ALOGPS
logP3.41ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity103.23 m³·mol⁻¹ChemAxon
Polarizability40.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H34O5
IUPAC name(15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid
InChI IdentifierInChI=1S/C20H34O5/c1-2-3-9-12-17(21)15-16-19(23)18(22)13-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/t17-,18?,19?/m0/s1
InChI KeyPRMWQIVYOYCJQC-VIQWUECVSA-N
Isomeric SMILES[H][C@](O)(CCCCC)C=CC(O)C(O)CC=CCC=CCCCC(O)=O
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
Classification
Description belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Polyol
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID10128338
ChEMBL IDNot Available
KEGG Compound IDC14782
Pubchem Compound ID11954043
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04684
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference