Human Metabolome Database Version 3.5

Showing metabocard for Thromboxane (HMDB03208)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:41 -0600
Update Date 2013-02-08 17:12:21 -0700
HMDB ID HMDB03208
Secondary Accession Numbers None
Metabolite Identification
Common Name Thromboxane
Description Thromboxane is a member of the family of lipids known as eicosanoids. It is produced in platelets by thromboxane synthetase, which is produced from the endoperoxides by the cyclooxygenase (COX) enzyme from arachidonic acid. -- Wikipedia; Thromboxane is a vasoconstrictor, potent hypertensive agent, and facilitates the clumping of platelets. It is in homeostatic balance in the circulatory system with prostacyclin, a related compound. The widely-used drug aspirin acts by inhibiting the ability of the COX enzyme to synthesize the precursors of thromboxane within platelets. -- WikipediaThromboxanes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Thromboxane A2
Chemical Formula C20H40O
Average Molecular Weight 296.531
Monoisotopic Molecular Weight 296.307915902
IUPAC Name (2R,3S)-3-heptyl-2-octyloxane
Traditional IUPAC Name (2R,3S)-3-heptyl-2-octyloxane
CAS Registry Number 66719-58-2
SMILES CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC
InChI Identifier InChI=1S/C20H40O/c1-3-5-7-9-11-13-17-20-19(16-14-18-21-20)15-12-10-8-6-4-2/h19-20H,3-18H2,1-2H3/t19-,20+/m0/s1
InChI Key RZWIIPASKMUIAC-VQTJNVASSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Oxanes
Sub Class N/A
Other Descriptors
  • N/A
Substituents
  • Dialkyl Ether
Direct Parent Oxanes
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
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
LogP 8.56 ALOGPS
LogP 7.61 ChemAxon
LogS -7.39 ALOGPS
pKa (strongest basic) -4.1 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 9.23 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 93.78 ChemAxon
Polarizability 41.15 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Skeletal Muscle
  • Fibroblasts
  • Placenta
  • Kidney
  • Lung
  • Nerve Cells
  • Platelet
  • Spleen
  • Smooth Muscle
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
0.000126 +/- 1.755e-05 uM Not Specified Not Specified Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000591 +/- 0.000129 uM Adult (>18 years old) Not Specified Spinal cord injuries (acute stage)
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 FDB023124
KNApSAcK ID Not Available
Chemspider ID 102829 Link_out
KEGG Compound ID C02198 Link_out
BioCyc ID ALPHA11-ALPHA-EPOXY-15-HYDROXYTHROMBA Link_out
BiGG ID 39305 Link_out
Wikipedia Link Thromboxane Link_out
NuGOwiki Link HMDB03208 Link_out
Metagene Link HMDB03208 Link_out
METLIN ID 415 Link_out
PubChem Compound 114873 Link_out
PDB ID Not Available
ChEBI ID 1221363 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Gurbel PA, Gattis WA, Fuzaylov SF, Gaulden L, Hasselblad V, Serebruany VL, O'Connor CM: Evaluation of platelets in heart failure: is platelet activity related to etiology, functional class, or clinical outcomes? Am Heart J. 2002 Jun;143(6):1068-75. Pubmed: 12075265 Link_out
  2. Rocca B, Ciabattoni G, Tartaglione R, Cortelazzo S, Barbui T, Patrono C, Landolfi R: Increased thromboxane biosynthesis in essential thrombocythemia. Thromb Haemost. 1995 Nov;74(5):1225-30. Pubmed: 8607099 Link_out
  3. Dong WG, Liu SP, Zhu HH, Luo HS, Yu JP: Abnormal function of platelets and role of angelica sinensis in patients with ulcerative colitis. World J Gastroenterol. 2004 Feb 15;10(4):606-9. Pubmed: 14966927 Link_out
  4. van Genderen PJ, Prins FJ, Michiels JJ, Schror K: Thromboxane-dependent platelet activation in vivo precedes arterial thrombosis in thrombocythaemia: a rationale for the use of low-dose aspirin as an antithrombotic agent. Br J Haematol. 1999 Mar;104(3):438-41. Pubmed: 10086775 Link_out
  5. FitzGerald GA, Oates JA, Hawiger J, Maas RL, Roberts LJ 2nd, Lawson JA, Brash AR: Endogenous biosynthesis of prostacyclin and thromboxane and platelet function during chronic administration of aspirin in man. J Clin Invest. 1983 Mar;71(3):676-88. Pubmed: 6338043 Link_out
  6. Karamouzis M, Langberg H, Skovgaard D, Bulow J, Kjaer M, Saltin B: In situ microdialysis of intramuscular prostaglandin and thromboxane in contracting skeletal muscle in humans. Acta Physiol Scand. 2001 Jan;171(1):71-6. Pubmed: 11350265 Link_out
  7. Wacker MJ, Tyburski JB, Ammar CP, Adams MC, Orr JA: Detection of thromboxane A(2) receptor mRNA in rabbit nodose ganglion neurons. Neurosci Lett. 2005 Sep 30;386(2):121-6. Pubmed: 15992996 Link_out
  8. Pfister SL, Hughes MJ, Rosolowsky M, Campbell WB: Role of contaminating platelets in thromboxane synthesis in primary cultures of human umbilical vein endothelial cells. Prostaglandins Other Lipid Mediat. 2002 Sep;70(1-2):39-49. Pubmed: 12428677 Link_out
  9. Hsu CY, Halushka PV, Hogan EL, Cox RD: Increased thromboxane level in experimental spinal cord injury. J Neurol Sci. 1986 Jul;74(2-3):289-96. Pubmed: 3525758 Link_out
  10. Dogne JM, de Leval X, Delarge J, David JL, Masereel B: New trends in thromboxane and prostacyclin modulators. Curr Med Chem. 2000 Jun;7(6):609-28. Pubmed: 10702629 Link_out
  11. Habib A, Vezza R, Creminon C, Maclouf J, FitzGerald GA: Rapid, agonist-dependent phosphorylation in vivo of human thromboxane receptor isoforms. Minimal involvement of protein kinase C. J Biol Chem. 1997 Mar 14;272(11):7191-200. Pubmed: 9054415 Link_out
  12. Vericel E, Calzada C, Chapuy P, Lagarde M: The influence of low intake of n-3 fatty acids on platelets in elderly people. Atherosclerosis. 1999 Nov 1;147(1):187-92. Pubmed: 10525140 Link_out
  13. Conti S, Desideri N, Passaghe S, Castagnoli MN, Cerletti C, Stein ML: Inhibition of thromboxane biosynthesis by 3-pyridinol carboxypentyl ethers substituted with a hydroxylated octyl chain. J Pharm Pharmacol. 1988 Feb;40(2):144-6. Pubmed: 2897452 Link_out
  14. Ylikorkala O, Makila UM, Viinikka L: Amniotic fluid prostacyclin and thromboxane in normal, preeclamptic, and some other complicated pregnancies. Am J Obstet Gynecol. 1981 Nov 1;141(5):487-90. Pubmed: 6895277 Link_out
  15. Stuart M, Wu J, Sunderji S, Ganley C: Effect of amniotic fluid on platelet thromboxane production. J Pediatr. 1987 Feb;110(2):289-92. Pubmed: 3806304 Link_out
  16. Shimura S, Sasaki T, Ishihara H, Satoh M, Masuda T, Sasaki H, Takishima T: [Airway hyperresponsiveness and mucus secretion] Nihon Kyobu Shikkan Gakkai Zasshi. 1990 Oct;28(10):1299-304. Pubmed: 1703251 Link_out
  17. Chehrazi BB, Giri S, Joy RM: Prostaglandins and vasoactive amines in cerebral vasospasm after aneurysmal subarachnoid hemorrhage. Stroke. 1989 Feb;20(2):217-24. Pubmed: 2465585 Link_out
  18. Mello SB, Barros DM, Silva AS, Laurindo IM, Novaes GS: Methotrexate as a preferential cyclooxygenase 2 inhibitor in whole blood of patients with rheumatoid arthritis. Rheumatology (Oxford). 2000 May;39(5):533-6. Pubmed: 10852985 Link_out
  19. De La Cruz JP, Villalobos MA, Escalante R, Guerrero A, Arrebola MM, Sanchez de La Cuesta F: Effects of the selective inhibition of platelet thromboxane synthesis on the platelet-subendothelium interaction. Br J Pharmacol. 2002 Dec;137(7):1082-8. Pubmed: 12429581 Link_out

Enzymes
Name: Thromboxane-A synthase
Reactions: Not Available
Gene Name: TBXAS1
Uniprot ID: P24557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Thromboxane A2 receptor
Reactions: Not Available
Gene Name: TBXA2R
Uniprot ID: P21731 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA