Record Information
Version3.6
Creation Date2006-08-14 00:24:46 UTC
Update Date2013-05-29 19:40:45 UTC
HMDB IDHMDB04684
Secondary Accession NumbersNone
Metabolite Identification
Common 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 ).
Structure
Thumb
Synonyms
  1. 11,12,15-TriHETRE
  2. 11,12,15-Trihydroxyicosatrienoate
  3. 11,12,15-Trihydroxyicosatrienoic acid
  4. 11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoate
  5. 11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoic acid
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid
Traditional IUPAC Name(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=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)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1
InChI KeyPRMWQIVYOYCJQC-YZSNCDGGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroxyeicosatrienoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • 1,2 Diol
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct ParentHydroxyeicosatrienoic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area97.99ChemAxon
rotatable bond count15ChemAxon
refractivity103.23ChemAxon
polarizability40.45ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified<0.1 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified<0.1 uMAdult (>18 years old)Not SpecifiedCommentNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023403
KNApSAcK IDNot Available
Chemspider ID10128338
KEGG Compound IDC14782
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04684
Metagene LinkHMDB04684
METLIN IDNot Available
PubChem Compound11954043
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Campbell WB, Spitzbarth N, Gauthier KM, Pfister SL: 11,12,15-Trihydroxyeicosatrienoic acid mediates ACh-induced relaxations in rabbit aorta. Am J Physiol Heart Circ Physiol. 2003 Dec;285(6):H2648-56. Epub 2003 Aug 7. Pubmed: 12907422
  2. Tang X, Edwards EM, Holmes BB, Falck JR, Campbell WB: Role of phospholipase C and diacylglyceride lipase pathway in arachidonic acid release and acetylcholine-induced vascular relaxation in rabbit aorta. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H37-45. Epub 2005 Jul 15. Pubmed: 16024567
  3. Zhang DX, Gauthier KM, Chawengsub Y, Holmes BB, Campbell WB: Cyclooxygenase- and lipoxygenase-dependent relaxation to arachidonic acid in rabbit small mesenteric arteries. Am J Physiol Heart Circ Physiol. 2005 Jan;288(1):H302-9. Epub 2004 Sep 23. Pubmed: 15388505
  4. Pfister SL, Spitzbarth N, Zeldin DC, Lafite P, Mansuy D, Campbell WB: Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450. Arch Biochem Biophys. 2003 Dec 1;420(1):142-52. Pubmed: 14622984

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2C18
Uniprot ID:
P33260
Gene Name:
CYP2F1
Uniprot ID:
P24903
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Gene Name:
CYP2B6
Uniprot ID:
P20813
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP4B1
Uniprot ID:
P13584
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP19A1
Uniprot ID:
P11511
Gene Name:
CYP2C8
Uniprot ID:
P10632
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Gene Name:
CYP2J2
Uniprot ID:
P51589
Gene Name:
CYP2A7
Uniprot ID:
P20853
Gene Name:
CYP2A6
Uniprot ID:
P11509
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0