Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2006-08-14 00:16:00 UTC |
---|
Update Date | 2022-03-07 02:49:21 UTC |
---|
HMDB ID | HMDB0004680 |
---|
Secondary Accession Numbers | |
---|
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 | CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O 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 |
---|
Synonyms | Value | Source |
---|
(16R,5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyicosa-5,8,11,14-tetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z,16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid | ChEBI | (all-cis)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoic acid | ChEBI | (all-Z)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoic acid | ChEBI | 16(R)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoic acid | ChEBI | 16(R)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid | ChEBI | (16R,5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoate | Generator | (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoate | Generator | (5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyicosa-5,8,11,14-tetraenoate | Generator | (5Z,8Z,11Z,14Z,16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoate | Generator | (all-cis)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoate | Generator | (all-Z)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoate | Generator | 16(R)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoate | Generator | 16(R)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate | Generator | 16-HETE | HMDB | 16R-HETE | HMDB | 16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate | HMDB | 16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid | HMDB |
|
---|
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 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 |
---|
Description | Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Eicosanoids |
---|
Direct Parent | Hydroxyeicosatetraenoic acids |
---|
Alternative Parents | |
---|
Substituents | - Hydroxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular 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 |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
16(R)-HETE,1TMS,isomer #1 | CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2671.3 | Semi standard non polar | 33892256 | 16(R)-HETE,1TMS,isomer #2 | CCCC[C@@H](O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2555.5 | Semi standard non polar | 33892256 | 16(R)-HETE,2TMS,isomer #1 | CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2614.9 | Semi standard non polar | 33892256 | 16(R)-HETE,1TBDMS,isomer #1 | CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2892.5 | Semi standard non polar | 33892256 | 16(R)-HETE,1TBDMS,isomer #2 | CCCC[C@@H](O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 2799.6 | Semi standard non polar | 33892256 | 16(R)-HETE,2TBDMS,isomer #1 | CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3113.4 | Semi standard non polar | 33892256 |
|
---|
General References | - 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 ]
- 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 ]
- Jacobs ER, Zeldin DC: The lung HETEs (and EETs) up. Am J Physiol Heart Circ Physiol. 2001 Jan;280(1):H1-H10. [PubMed:11123211 ]
- Natarajan R, Reddy MA: HETEs/EETs in renal glomerular and epithelial cell functions. Curr Opin Pharmacol. 2003 Apr;3(2):198-203. [PubMed:12681244 ]
- 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 ]
|
---|