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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:35 UTC
HMDB IDHMDB01452
Secondary Accession NumbersNone
Metabolite Identification
Common NameThromboxane A2
DescriptionThromboxane A2 is an unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).Thromboxanes 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
Synonyms
  1. (1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-Heptenoate
  2. (1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-Heptenoic acid
  3. (5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-Heptenoate
  4. (5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-Heptenoic acid
  5. (5Z,13E)-(15S)-9,11-epoxy-15-hydroxythromba-5,13-dienoate
  6. (5Z,13E)-(15S)-9,11-epoxy-15-hydroxythromba-5,13-dienoic acid
  7. (5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoate
  8. (5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acid
  9. (5Z,13E)-(15S)-9a,11a-epoxy-15-Hydroxythromboxa-5,13-dienoate
  10. (5Z,13E)-(15S)-9a,11a-epoxy-15-Hydroxythromboxa-5,13-dienoic acid
  11. (5Z,13E)-(15S)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoate
  12. (5Z,13E)-(15S)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoic acid
  13. (5Z,9alpha,11alpha,13E,15S)-9,11-epoxy-15-hydroxy-Thromboxa-5,13-dien-1-oate
  14. (5Z,9alpha,11alpha,13E,15S)-9,11-epoxy-15-hydroxy-Thromboxa-5,13-dien-1-oic acid
  15. (5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-oate
  16. (5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-oic acid
  17. 7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-Heptenoate
  18. 7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-Heptenoic acid
  19. 9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-oate
  20. 9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-oic acid
  21. Cid
  22. Rabbit aorta contracting substance
  23. RCS
  24. TXA-2
  25. TXA2
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid
Traditional Namethromboxane A2
CAS Registry Number57576-52-0
SMILES
CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1
InChI KeyDSNBHJFQCNUKMA-SCKDECHMSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassThromboxanes
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Heterocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Acetal
  • Allyl Alcohol
  • Carboxylic Acid
  • Meta Dioxane
  • Oxane
  • Oxetane
  • Secondary Alcohol
Direct ParentThromboxanes
Ontology
StatusDetected 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
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.047ALOGPS
logP4.31ALOGPS
logP4.08ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity97.67 m3·mol-1ChemAxon
Polarizability39.99 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Platelet
  • Smooth Muscle
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00024 +/- 0.000036 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00045 +/- 0.000047 uMChildren (1-13 years old)BothCoronary heart disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0029 (0.00021-0.0136) uMNot SpecifiedNot SpecifiedAcute lymphoblastic leukemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00346 uMNot SpecifiedNot SpecifiedBronchopulmonary dysplasia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00062 uMNot SpecifiedNot SpecifiedBurkitt's lymphoma details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00237 uMNot SpecifiedNot SpecifiedHead injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00057 (0.0005-0.00063) uMNot SpecifiedNot SpecifiedLymphoblastic lymphoma details
UrineDetected and Quantified0.00078 +/- 0.00035 umol/mmol creatinineAdult (>18 years old)BothHepatocellular carcinoma details
Associated Disorders and Diseases
Disease References
Coronary heart disease
  1. Akimova EV: Prostacyclin and thromboxane A2 levels in children and adolescents with an inherited predisposition to coronary heart disease: a family study. Coron Artery Dis. 1994 Sep;5(9):761-5. Pubmed: 7858766
Hepatocellular carcinoma
  1. Matsumata T, Yamamoto K, Shirabe K, Shimada M, Sugimachi K, Takesue F, Muto Y, Ikeda T: Urinary excretion of prostaglandins and renal function after hepatic resection. Hepatogastroenterology. 1997 May-Jun;44(15):774-8. Pubmed: 9222688
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022632
KNApSAcK IDNot Available
Chemspider ID4444137
KEGG Compound IDC02198
BioCyc IDALPHA11-ALPHA-EPOXY-15-HYDROXYTHROMBA
BiGG ID39305
Wikipedia LinkThromboxane A2
NuGOwiki LinkHMDB01452
Metagene LinkHMDB01452
METLIN ID6253
PubChem Compound5280497
PDB IDNot Available
ChEBI ID15627
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wu X, Dev A, Leong AB: Zileuton, a 5-lipoxygenase inhibitor, increases production of thromboxane A2 and platelet aggregation in patients with asthma. Am J Hematol. 2003 Sep;74(1):23-5. Pubmed: 12949886
  2. Feldman M, Cryer B, Rushin K, Betancourt J: A comparison of every-third-day versus daily low-dose aspirin therapy on serum thromboxane concentrations in healthy men and women. Clin Appl Thromb Hemost. 2001 Jan;7(1):53-7. Pubmed: 11190906
  3. Kobayashi T, Suzuki J, Watanabe M, Suzuki S, Yoshida K, Kume K, Suzuki H: Changes in platelet calcium concentration by thromboxane A2 stimulation in patients with nephrotic syndrome of childhood. Nephron. 1997;77(3):309-14. Pubmed: 9375825
  4. Amari T, Kubo K, Kobayashi T, Sekiguchi M: Effects of recombinant human superoxide dismutase on tumor necrosis factor-induced lung injury in awake sheep. J Appl Physiol. 1993 Jun;74(6):2641-8. Pubmed: 8396104
  5. Hada S, Hashizume M, Yoshioka F, Nishii S, Yasunaga K: [Measurement of platelet thromboxane A2/prostaglandin H2 receptor in asthmatic patients] Arerugi. 1993 May;42(5):609-16. Pubmed: 8323459
  6. Cattaneo M, Lombardi R, Zighetti ML, Gachet C, Ohlmann P, Cazenave JP, Mannucci PM: Deficiency of (33P)2MeS-ADP binding sites on platelets with secretion defect, normal granule stores and normal thromboxane A2 production. Evidence that ADP potentiates platelet secretion independently of the formation of large platelet aggregates and thromboxane A2 production. Thromb Haemost. 1997 May;77(5):986-90. Pubmed: 9184415
  7. Schror K: The effect of prostaglandins and thromboxane A2 on coronary vessel tone--mechanisms of action and therapeutic implications. Eur Heart J. 1993 Nov;14 Suppl I:34-41. Pubmed: 7507439
  8. Marttunen MB, Pyrhonen S, Tiitinen AE, Viinikka LU, Ylikorkala O: Effect of antiestrogen regimen on prostacyclin and thromboxane A2 in postmenopausal patients with breast cancer: evidence of significance of hypertension, smoking or previous use of estrogen therapy. Prostaglandins. 1996 Oct;52(4):317-26. Pubmed: 8936586
  9. Tanaka K, Roberts MH, Yamamoto N, Sugiura H, Uehara M, Mao XQ, Shirakawa T, Hopkin JM: Genetic variants of the receptors for thromboxane A2 and IL-4 in atopic dermatitis. Biochem Biophys Res Commun. 2002 Apr 5;292(3):776-80. Pubmed: 11922633
  10. Leonhardt A, Bernert S, Watzer B, Schmitz-Ziegler G, Seyberth HW: Low-dose aspirin in pregnancy: maternal and neonatal aspirin concentrations and neonatal prostanoid formation. Pediatrics. 2003 Jan;111(1):e77-81. Pubmed: 12509599
  11. Sheu JR, Hsiao G, Shen MY, Lin WY, Tzeng CR: The hyperaggregability of platelets from normal pregnancy is mediated through thromboxane A2 and cyclic AMP pathways. Clin Lab Haematol. 2002 Apr;24(2):121-9. Pubmed: 11985559
  12. Djellas Y, Manganello JM, Antonakis K, Le Breton GC: Identification of Galpha13 as one of the G-proteins that couple to human platelet thromboxane A2 receptors. J Biol Chem. 1999 May 14;274(20):14325-30. Pubmed: 10318854
  13. Rocca B, Ranelletti FO, Maggiano N, Ciabattoni G, De Cristofaro R, Landolfi R: Inherited macrothrombocytopenia with distinctive platelet ultrastructural and functional features. Thromb Haemost. 2000 Jan;83(1):35-41. Pubmed: 10669151
  14. Liel N, Nathan I, Yermiyahu T, Zolotov Z, Lieberman JR, Dvilansky A, Halushka PV: Increased platelet thromboxane A2/prostaglandin H2 receptors in patients with pregnancy induced hypertension. Thromb Res. 1993 May 1;70(3):205-10. Pubmed: 8327985
  15. Modesti PA, Colella A, Cecioni I, Costoli A, Biagini D, Migliorini A, Neri Serneri GG: Increased number of thromboxane A2-prostaglandin H2 platelet receptors in active unstable angina and causative role of enhanced thrombin formation. Am Heart J. 1995 May;129(5):873-9. Pubmed: 7732975
  16. Storlien LH, Kriketos AD, Calvert GD, Baur LA, Jenkins AB: Fatty acids, triglycerides and syndromes of insulin resistance. Prostaglandins Leukot Essent Fatty Acids. 1997 Oct;57(4-5):379-85. Pubmed: 9430382
  17. Wennmalm A, Benthin G, Granstrom EF, Persson L, Winell S: Maintained hyperexcretion of thromboxane A2 metabolite in healthy young cigarette smokers: results from a prospective study in randomly sampled males with stable smoking habits. Clin Physiol. 1993 May;13(3):257-64. Pubmed: 8519161
  18. Ogawa S, Takeuchi K, Sugimura K, Sato C, Fukuda M, Lee R, Ito S, Sato T: The 5-HT2 receptor antagonist sarpogrelate reduces urinary and plasma levels of thromboxane A2 and urinary albumin excretion in non-insulin-dependent diabetes mellitus patients. Clin Exp Pharmacol Physiol. 1999 May-Jun;26(5-6):461-4. Pubmed: 10386239
  19. Michelson AD, Wencel-Drake JD, Kestin AS, Barnard MR: Platelet activation results in a redistribution of glycoprotein IV (CD36). Arterioscler Thromb. 1994 Jul;14(7):1193-201. Pubmed: 7517184
  20. Komiotis D, Wencel-Drake JD, Dieter JP, Lim CT, Le Breton GC: Labeling of human platelet plasma membrane thromboxane A2/prostaglandin H2 receptors using SQB, a novel biotinylated receptor probe. Biochem Pharmacol. 1996 Sep 13;52(5):763-70. Pubmed: 8765474

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
TBXAS1
Uniprot ID:
P24557
Molecular weight:
60648.885
Reactions
Prostaglandin H2 → Thromboxane A2details
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for thromboxane A2 (TXA2), a potent stimulator of platelet aggregation. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction. Activates phospholipase C. Isoform 1 activates adenylyl cyclase. Isoform 2 inhibits adenylyl cyclase
Gene Name:
TBXA2R
Uniprot ID:
P21731
Molecular weight:
37430.7
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q53F23
Molecular weight:
60648.9