Human Metabolome Database Version 3.5

Showing metabocard for 16(R)-HETE (HMDB04680)

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 Link_out, 14626496 Link_out, 12681244 Link_out, 11123211 Link_out, 14552765 Link_out, 11126912 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 16-HETE
  2. 16R-HETE
  3. 16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate
  4. 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
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct Parent Hydroxyeicosatetraenoic 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 0.002 g/L ALOGPS
LogP 5.77 ALOGPS
LogP 5.36 ChemAxon
LogS -5.21 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -1.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 101.47 ChemAxon
Polarizability 37.28 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 Reference
Blood Detected and Quantified
0.000277 +/- 8.6E-5 uM Adult (>18 years old) Both Normal
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 FDB023401
KNApSAcK ID Not Available
Chemspider ID 7827807 Link_out
KEGG Compound ID C14778 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04680 Link_out
Metagene Link HMDB04680 Link_out
METLIN ID Not Available
PubChem Compound 9548884 Link_out
PDB ID Not Available
ChEBI ID 34162 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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 Link_out
  2. 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 Link_out
  3. Natarajan R, Reddy MA: HETEs/EETs in renal glomerular and epithelial cell functions. Curr Opin Pharmacol. 2003 Apr;3(2):198-203. Pubmed: 12681244 Link_out
  4. Jacobs ER, Zeldin DC: The lung HETEs (and EETs) up. Am J Physiol Heart Circ Physiol. 2001 Jan;280(1):H1-H10. Pubmed: 11123211 Link_out
  5. 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 Link_out
  6. 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 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