| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-08-13 18:16:00 -0600 |
| Update Date |
2013-05-29 13:40:44 -0600 |
| HMDB ID |
HMDB04680 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
16(R)-HETE |
| Description |
16(R)-HETE is a metabolite of arachidonic acid, metabolized by the enzyme Cytochrome P450, family 2, subfamily C [EC:1.14.13.80 1.14.13.48 1.14.13.49]. 16(R)-HETE is an endogenous lipidic inhibitor of human neutrophil inhibitor of adhesion and aggregation activity. Human polymorphonuclear leukocytes (PMNs) produce 16(R)-HETE that modulates their function. HETEs have different biological properties based on sites of production and can be stored in tissue lipids and released in response to hormonal stimuli. Eicosanoids generated during the actions of growth factors and vasoconstrictors can modulate disease processes by affecting vascular homeostasis, inflammation, cellular growth, apoptosis and oxidant stress. In lung, the presence of these eicosanoids in the pulmonary vasculature and airways, including effects on pulmonary vascular and bronchial smooth muscle tone and airway epithelial ion transport. (PMID: 16258232  , 14626496 , 12681244 , 11123211 , 14552765 , 11126912 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 16-HETE
- 16R-HETE
- 16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate
- 16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
|
| Chemical Formula |
C20H32O3 |
| Average Molecular Weight |
320.4663 |
| Monoisotopic Molecular Weight |
320.23514489 |
| IUPAC Name |
(5Z,8Z,11Z,14Z,16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid |
| Traditional IUPAC Name |
16R-hete |
| CAS Registry Number |
Not Available |
| SMILES |
CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O |
| InChI Identifier |
InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14-/t19-/m1/s1 |
| InChI Key |
JEKNPVYFNMZRJG-STHMYGMFSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Eicosanoids |
| Sub Class |
Hydroxyeicosatetraenoic Acids |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- Hydroxy Fatty Acids
- Organic Compounds
- Straight Chain Fatty Acids
- Unsaturated Fatty Acids
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| Substituents |
- Acyclic Alkene
- Allyl Alcohol
- Carboxylic Acid
- Secondary Alcohol
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| Direct Parent |
Hydroxyeicosatetraenoic Acids |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
|
| 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 |
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| Predicted Properties |
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| Spectra |
|---|
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Not Available
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| Biological Properties |
|---|
| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
Not Available
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| Pathways |
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.000277 +/- 8.6E-5 uM |
Adult (>18 years old) |
Both |
Normal
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| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023401 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
7827807 |
| KEGG Compound ID |
C14778 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB04680 |
| Metagene Link |
HMDB04680 |
| METLIN ID |
Not Available |
| PubChem Compound |
9548884 |
| PDB ID |
Not Available |
| ChEBI ID |
34162 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
- Miyata N, Roman RJ: Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system. J Smooth Muscle Res. 2005 Aug;41(4):175-93.
Pubmed: 16258232
- Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71.
Pubmed: 14626496
- Natarajan R, Reddy MA: HETEs/EETs in renal glomerular and epithelial cell functions. Curr Opin Pharmacol. 2003 Apr;3(2):198-203.
Pubmed: 12681244
- Jacobs ER, Zeldin DC: The lung HETEs (and EETs) up. Am J Physiol Heart Circ Physiol. 2001 Jan;280(1):H1-H10.
Pubmed: 11123211
- Reddy YK, Reddy LM, Capdevila JH, Falck JR: Practical, asymmetric synthesis of 16-hydroxyeicosa-5(Z),8(Z), 11(Z),14(Z)-tetraenoic acid (16-HETE), an endogenous inhibitor of neutrophil activity. Bioorg Med Chem Lett. 2003 Nov 3;13(21):3719-20.
Pubmed: 14552765
- Bednar MM, Gross CE, Russell SR, Fuller SP, Ahern TP, Howard DB, Falck JR, Reddy KM, Balazy M: 16(R)-hydroxyeicosatetraenoic acid, a novel cytochrome P450 product of arachidonic acid, suppresses activation of human polymorphonuclear leukocyte and reduces intracranial pressure in a rabbit model of thromboembolic stroke. Neurosurgery. 2000 Dec;47(6):1410-8; discussion 1418-9.
Pubmed: 11126912
|
