Human Metabolome Database Version 3.5

Showing metabocard for Thromboxane A2 (HMDB01452)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:35 -0700
HMDB ID HMDB01452
Secondary Accession Numbers None
Metabolite Identification
Common Name Thromboxane A2
Description Thromboxane 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H32O5
Average Molecular Weight 352.4651
Monoisotopic Molecular Weight 352.224974134
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 IUPAC Name thromboxane A2
CAS Registry Number 57576-52-0
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 Key DSNBHJFQCNUKMA-SCKDECHMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Thromboxanes
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 Parent Thromboxanes
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
  • 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
Water Solubility 0.047 g/L ALOGPS
LogP 4.31 ALOGPS
LogP 4.08 ChemAxon
LogS -3.88 ALOGPS
pKa (strongest acidic) 4.27 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 75.99 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 97.67 ChemAxon
Polarizability 39.99 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not 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
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
0.00024 +/- 0.000036 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.00045 +/- 0.000047 uM Children (1-13 year old) Both Coronary heart disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0029 (0.00021-0.0136) uM Not Specified Not Specified Acute lymphoblastic leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00346 uM Not Specified Not Specified Bronchopulmonary dysplasia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00062 uM Not Specified Not Specified Burkitt's lymphoma
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00237 uM Not Specified Not Specified Head injury
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00057 (0.0005-0.00063) uM Not Specified Not Specified Lymphoblastic lymphoma
Urine Detected and Quantified 0.00078 +/- 0.00035 umol/mmol creatinine Adult (>18 years old) Both Hepatocellular carcinoma
Associated Disorders and Diseases
Disease References
Coronary heart disease
  • 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 Link_out
      Hepatocellular carcinoma
      • 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 Link_out
          Associated OMIM IDs
          • 114550 Link_out (Hepatocellular carcinoma)
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB022632
          KNApSAcK ID Not Available
          Chemspider ID 4444137 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 A2 Link_out
          NuGOwiki Link HMDB01452 Link_out
          Metagene Link HMDB01452 Link_out
          METLIN ID 6253 Link_out
          PubChem Compound 5280497 Link_out
          PDB ID Not Available
          ChEBI ID 15627 Link_out
          References
          Synthesis Reference Not 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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out

          Enzymes
          Name: Thromboxane-A synthase
          Reactions:
          Prostaglandin H2 unknown Thromboxane A2 details
          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
          Name: HCG14925, isoform CRA_a
          Reactions: Not Available
          Gene Name: Not Available
          Uniprot ID: Q53F23 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA