Human Metabolome Database Version 3.5

Showing metabocard for 11,14,15-THETA (HMDB04694)

Record Information
Version 3.5
Creation Date 2006-08-13 18:42:32 -0600
Update Date 2013-05-29 13:40:51 -0600
HMDB ID HMDB04694
Secondary Accession Numbers None
Metabolite Identification
Common Name 11,14,15-THETA
Description 11,14,15-trihydroxyeicosatrienoic acid (11,14,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). Increased amounts of 11,14,15-THETA are synthesized in subacute hypoxia. Prolonged exposure to reduced PO2 activates 15-LO in small pulmonary arteries (PA); activation of 15-LO is associated with translocation of the enzyme from the cytosol to membrane. 11,14,15-THETA is an endothelium-derived relaxing factor. (PMID: 12690037 Link_out, 9812980 Link_out, 15388505 Link_out, 14622984 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (5Z,8Z,12E)-11,14,15-Trihydroxyeicosa-5,8,12-trienoate
  2. (5Z,8Z,12E)-11,14,15-Trihydroxyeicosa-5,8,12-trienoic acid
  3. (5Z,8Z,12E)-11,14,15-Trihydroxyicosa-5,8,12-trienoate
  4. (5Z,8Z,12E)-11,14,15-Trihydroxyicosa-5,8,12-trienoic acid
  5. 11,14,15-Trihydroxy-5Z,8Z,12E-eicosatrienoate
  6. 11,14,15-Trihydroxy-5Z,8Z,12E-eicosatrienoic acid
  7. 11,14,15-Trihydroxyicosatrienoate
  8. 11,14,15-Trihydroxyicosatrienoic acid
Chemical Formula C20H34O5
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240624198
IUPAC Name (5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid
Traditional IUPAC Name (5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid
CAS Registry Number Not Available
SMILES CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O
InChI Identifier InChI=1S/C20H34O5/c1-2-3-9-13-18(22)19(23)16-15-17(21)12-10-7-5-4-6-8-11-14-20(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+
InChI Key YCFPVUKKIWMCJK-LTCHCNGXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroxyeicosatrienoic 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 Parent Hydroxyeicosatrienoic Acids
Ontology
Status Expected and Not 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.053 g/L ALOGPS
LogP 4.47 ALOGPS
LogP 3.41 ChemAxon
LogS -3.82 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 103.23 ChemAxon
Polarizability 41.29 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023410
KNApSAcK ID Not Available
Chemspider ID 10128354 Link_out
KEGG Compound ID C14814 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04694 Link_out
Metagene Link HMDB04694 Link_out
METLIN ID Not Available
PubChem Compound 11954059 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Zhu D, Medhora M, Campbell WB, Spitzbarth N, Baker JE, Jacobs ER: Chronic hypoxia activates lung 15-lipoxygenase, which catalyzes production of 15-HETE and enhances constriction in neonatal rabbit pulmonary arteries. Circ Res. 2003 May 16;92(9):992-1000. Epub 2003 Apr 10. Pubmed: 12690037 Link_out
  2. Pfister SL, Spitzbarth N, Nithipatikom K, Edgemond WS, Falck JR, Campbell WB: Identification of the 11,14,15- and 11,12, 15-trihydroxyeicosatrienoic acids as endothelium-derived relaxing factors of rabbit aorta. J Biol Chem. 1998 Nov 20;273(47):30879-87. Pubmed: 9812980 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions: Not Available
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions: Not Available
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C18
Reactions: Not Available
Gene Name: CYP2C18
Uniprot ID: P33260 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2F1
Reactions: Not Available
Gene Name: CYP2F1
Uniprot ID: P24903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4X1
Reactions: Not Available
Gene Name: CYP4X1
Uniprot ID: Q8N118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A13
Reactions: Not Available
Gene Name: CYP2A13
Uniprot ID: Q16696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4B1
Reactions: Not Available
Gene Name: CYP4B1
Uniprot ID: P13584 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4Z1
Reactions: Not Available
Gene Name: CYP4Z1
Uniprot ID: Q86W10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2S1
Reactions: Not Available
Gene Name: CYP2S1
Uniprot ID: Q96SQ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2J2
Reactions: Not Available
Gene Name: CYP2J2
Uniprot ID: P51589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A7
Reactions: Not Available
Gene Name: CYP2A7
Uniprot ID: P20853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions: Not Available
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: A0N0X8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: Q6NWU0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA