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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:24:06 UTC
HMDB IDHMDB0001452
Secondary Accession Numbers
  • HMDB01452
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
ValueSource
(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoateChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acidChEBI
9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-Oic acidChEBI
TXA-2ChEBI
TXA2ChEBI
(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoateGenerator
(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9α,11α-epoxy-15-hydroxythromboxa-5,13-dienoateGenerator
(5Z,13E)-(15S)-9α,11α-epoxy-15-hydroxythromboxa-5,13-dienoic acidGenerator
(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-OateGenerator
(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-OateGenerator
(5Z,9α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-OateGenerator
(5Z,9α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acidGenerator
9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-OateGenerator
(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoateHMDB
(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoic acidHMDB
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoateHMDB
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoic acidHMDB
(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoateHMDB
(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoateHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acidHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-OateHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-Oic acidHMDB
7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoateHMDB
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 acidHMDB
CidHMDB
Rabbit aorta contracting substanceHMDB
RCSHMDB
a2, ThromboxaneMeSH
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
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
DescriptionThis compound belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentThromboxanes
Alternative Parents
Substituents
  • Thromboxane
  • Long-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Meta-dioxane
  • Fatty acid
  • Oxane
  • Unsaturated fatty acid
  • Secondary alcohol
  • Oxetane
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Hepatobiliary disorders:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

    Element:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

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 Solubility0.047 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity97.67 m³·mol⁻¹ChemAxon
Polarizability39.99 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
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
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 (1985). 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