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Human Metabolome Database Version 3.5

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Showing metabocard for 11,12,15-THETA (HMDB04684)

Record Information
Version 3.5
Creation Date 2006-08-13 18:24:46 -0600
Update Date 2013-02-08 17:13:18 -0700
HMDB ID HMDB04684
Secondary Accession Numbers None
Metabolite Identification
Common Name 11,12,15-THETA
Description 11,12,15-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 Link_out, 16024567 Link_out, 15388505 Link_out, 14622984 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H34O5
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240624198
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 Number Not 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 Key PRMWQIVYOYCJQC-YZSNCDGGSA-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 Detected 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
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 0.052 g/L ALOGPS
LogP 4.46 ALOGPS
LogP 3.41 ChemAxon
LogS -3.83 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -2.8 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 40.45 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
<0.1 uM Adult (>18 years old) Not Specified Normal HM Replicate Plasma (n=3)
Blood Detected and Quantified
Article_icon
<0.1 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023403
KNApSAcK ID Not Available
Chemspider ID 10128338 Link_out
KEGG Compound ID C14782 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04684 Link_out
Metagene Link HMDB04684 Link_out
METLIN ID Not Available
PubChem Compound 11954043 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Cytochrome P450 3A4
Reactions:
  • (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
  • (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions:
  • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions:
  • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions:
  • --- []
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C18
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2C18
Uniprot ID: P33260 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2F1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2F1
Uniprot ID: P24903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4X1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP4X1
Uniprot ID: Q8N118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A13
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2A13
Uniprot ID: Q16696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4B1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP4B1
Uniprot ID: P13584 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4Z1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP4Z1
Uniprot ID: Q86W10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2S1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2S1
Uniprot ID: Q96SQ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2J2
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2J2
Uniprot ID: P51589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A7
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2A7
Uniprot ID: P20853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
Reactions:
    Gene Name: CYP1A1
    Uniprot ID: A0N0X8 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytochrome P450 2D6
    Reactions:
      Gene Name: CYP2D6
      Uniprot ID: Q6NWU0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA