| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:29:24 UTC |
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| Update date | 2015-07-21 06:57:41 UTC |
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| Primary ID | FDB023403 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 11,12,15-THETA |
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| 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, 16024567, 15388505, 14622984) [HMDB] |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoate | Generator | | (5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoic acid | Kegg | | (5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoate | Generator | | (5Z,8Z,13e)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoic acid | Kegg | | 11,12,15-TriHETRE | HMDB | | 11,12,15-Trihydroxyicosatrienoate | hmdb | | 11,12,15-Trihydroxyicosatrienoic acid | hmdb | | 11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoate | hmdb | | 11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoic acid | hmdb |
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| Predicted Properties | |
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| Chemical Formula | C20H34O5 |
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| IUPAC name | (15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid |
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| 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)/t17-,18?,19?/m0/s1 |
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| InChI Key | PRMWQIVYOYCJQC-VIQWUECVSA-N |
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| Isomeric SMILES | [H][C@](O)(CCCCC)C=CC(O)C(O)CC=CCC=CCCCC(O)=O |
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| Average Molecular Weight | 354.481 |
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| Monoisotopic Molecular Weight | 354.240624198 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Eicosanoids |
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| Direct Parent | Hydroxyeicosatrienoic acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | Not Available | |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 10128338 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C14782 |
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| Pubchem Compound ID | 11954043 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB04684 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Cytochrome P450, family 1, subfamily A, polypeptide 1 | CYP1A1 | A0N0X8 | | Cytochrome P450 2D6 | CYP2D6 | Q6NWU0 |
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| Pathways | |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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