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Record Information
Creation Date2006-05-22 15:12:44 UTC
Update Date2017-03-02 21:27:14 UTC
Secondary Accession Numbers
  • HMDB05070
Metabolite Identification
Common NameThromboxane B2
DescriptionThromboxanes. A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin). -- Pubchem. 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.
b2, ThromboxaneMeSH
Chemical FormulaC20H34O6
Average Molecular Weight370.4804
Monoisotopic Molecular Weight370.23553882
IUPAC Name(5Z)-7-[(2R,3S,4S)-4,6-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl]hept-5-enoic acid
Traditional Namethromboxane B2
CAS Registry Number54397-85-2
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentThromboxanes
Alternative Parents
  • Thromboxane
  • Long-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Oxane
  • Unsaturated fatty acid
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.25 mg/mLALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.18 m3·mol-1ChemAxon
Polarizability42.26 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
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
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Bladder
  • Epidermis
  • Lung
  • Muscle
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
Acetaminophen Action PathwaySMP00710Not Available
Acetylsalicylic Acid PathwaySMP00083Not Available
Antipyrine Action PathwaySMP00692Not Available
Antrafenine Action PathwaySMP00693Not Available
Arachidonic Acid MetabolismSMP00075map00590
Bromfenac PathwaySMP00102Not Available
Carprofen Action PathwaySMP00694Not Available
Celecoxib PathwaySMP00096Not Available
Diclofenac PathwaySMP00093Not Available
Diflunisal PathwaySMP00289Not Available
Etodolac PathwaySMP00084Not Available
Etoricoxib Action PathwaySMP00695Not Available
Fenoprofen Action PathwaySMP00696Not Available
Flurbiprofen Action PathwaySMP00697Not Available
Ibuprofen PathwaySMP00086Not Available
Indomethacin PathwaySMP00104Not Available
Ketoprofen PathwaySMP00085Not Available
Ketorolac PathwaySMP00098Not Available
Leukotriene C4 Synthesis DeficiencySMP00353Not Available
Lornoxicam Action PathwaySMP00700Not Available
Lumiracoxib Action PathwaySMP00699Not Available
Magnesium salicylate Action PathwaySMP00698Not Available
Mefanamic Acid PathwaySMP00109Not Available
Meloxicam PathwaySMP00106Not Available
Nabumetone PathwaySMP00114Not Available
Naproxen PathwaySMP00120Not Available
Nepafenac Action PathwaySMP00702Not Available
Oxaprozin PathwaySMP00113Not Available
Phenylbutazone Action PathwaySMP00701Not Available
Piroxicam PathwaySMP00077Not Available
Rofecoxib PathwaySMP00087Not Available
Salicylate-sodium Action PathwaySMP00708Not Available
Salicylic Acid Action PathwaySMP00709Not Available
Salsalate Action PathwaySMP00707Not Available
Sulindac PathwaySMP00094Not Available
Suprofen PathwaySMP00101Not Available
Tenoxicam Action PathwaySMP00706Not Available
Tiaprofenic Acid Action PathwaySMP00705Not Available
Tolmetin Action PathwaySMP00704Not Available
Trisalicylate-choline Action PathwaySMP00703Not Available
Valdecoxib PathwaySMP00116Not Available
Normal Concentrations
BloodDetected and Quantified0.00019 +/- 0.00007 uMAdult (>18 years old)Female
BloodDetected and Quantified0.00041 +/- 0.00018 uMAdult (>18 years old)Female
BloodDetected and Quantified0.00554 +/- 0.00235 uMAdult (>18 years old)Female
BloodDetected and Quantified0.01080 +/- 0.00370 uMAdult (>18 years old)Female
BloodDetected and Quantified0.48196 +/- 0.14576 uMAdult (>18 years old)Female
BloodDetected and Quantified0.0214 +/- 0.0409 uMAdult (>18 years old)Both
BloodDetected and Quantified0.000865 +/- 0.00018 uMAdult (>18 years old)Both
BloodDetected and Quantified0.95 +/- 0.24 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000919 +/- 0.0016 uMAdult (>18 years old)Both
BloodDetected and Quantified3.7E-5 +/- 7E-6 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00085 +/- 0.00015 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0024 +/- 0.00094 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0526 (0.0395-0.0658) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.027 +/- 0.048 uMAdult (>18 years old)Both
Ischemic heart disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.000267 uMChildren (1-13 years old)Not Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00220 (0.000583-0.00451) uMChildren (1-13 years old)Not Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00264 uMChildren (1-13 years old)Not Specifiedgunshot wound details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000107 uMNot SpecifiedNot SpecifiedHIV-Seropositive, Dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000467 +/- 0.000243 uMNot SpecifiedNot Specifiedhydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00172 (0.000945-0.00248) uMChildren (1-13 years old)Not SpecifiedHypoxia/Ischemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00289 (0.000594-0.00711) uMChildren (1-13 years old)Not Specifiedmeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0117 +/- 0.00177 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage with cerebral vasospasm details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0155 +/- 0.00243 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage without cerebral vasospasm details
Cerebrospinal Fluid (CSF)Detected and Quantified3.322e-05 uMNot SpecifiedNot SpecifiedHIV-Seropositive (Neurologically normal) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000032 +/- 0.00001 uMAdult (>18 years old)BothIntracranial tumours details
Associated Disorders and Diseases
Disease References
Brain tumors
  1. Walker V, Pickard JD, Smythe PJ, Perry S: Eicosanoid production by brain tumours in vivo--evidence for intracranial compartmentation. J Neurooncol. 1991 Dec;11(3):259-62. [PubMed:1823345 ]
Ischemic heart disease
  1. Renda G, Tacconelli S, Capone ML, Sacchetta D, Santarelli F, Sciulli MG, Zimarino M, Grana M, D'Amelio E, Zurro M, Price TS, Patrono C, De Caterina R, Patrignani P: Celecoxib, ibuprofen, and the antiplatelet effect of aspirin in patients with osteoarthritis and ischemic heart disease. Clin Pharmacol Ther. 2006 Sep;80(3):264-74. [PubMed:16952493 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023130
KNApSAcK IDNot Available
Chemspider ID4446261
KEGG Compound IDC05963
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThromboxane B2
NuGOwiki LinkHMDB03252
Metagene LinkHMDB03252
PubChem Compound5283137
PDB IDNot Available
ChEBI ID28728
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Laitinen O, Seppala E, Nissila M, Vapaatalo H: Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6. [PubMed:6589104 ]
  2. Janssen PL, Meyboom S, van Staveren WA, de Vegt F, Katan MB: Consumption of ginger (Zingiber officinale roscoe) does not affect ex vivo platelet thromboxane production in humans. Eur J Clin Nutr. 1996 Nov;50(11):772-4. [PubMed:8933126 ]
  3. Turi S, Bereczki C, Torday C, Havass Z, Nemeth M: The effects of bicarbonate and acetate haemodialysis on platelet cyclic AMP concentration, thromboxane B2 release and aggregation. Pediatr Nephrol. 1991 May;5(3):327-31. [PubMed:1651098 ]
  4. Vissinger H, Husted SE, Kristensen SD, Nielsen HK: Platelet-derived growth factor release and antiplatelet treatment with low-dose acetylsalicylic acid. Angiology. 1993 Aug;44(8):633-8. [PubMed:8342880 ]
  5. Pace-Asciak CR, Rounova O, Hahn SE, Diamandis EP, Goldberg DM: Wines and grape juices as modulators of platelet aggregation in healthy human subjects. Clin Chim Acta. 1996 Mar 15;246(1-2):163-82. [PubMed:8814965 ]
  6. Zahavi M, Zahavi J: Concomitant in vitro platelet hypofunction and increased thromboxane B2 (TXB2) generation and enhanced in vivo platelet activation. A distinct syndrome in thrombosis? Eur J Haematol. 1997 Oct;59(4):266-7. [PubMed:9338626 ]
  7. Nyyssonen K, Seppanen K, Salonen JT: High-performance liquid chromatographic assay of platelet-produced thromboxane B2. J Chromatogr. 1993 Jan 29;612(1):27-32. [PubMed:8454699 ]
  8. Anfossi G, Trovati M, Mularoni E, Massucco P, Cavalot F, Mattiello L, Emanuelli G: Effects of diltiazem on thromboxane B2 production from platelet-rich plasma and whole blood. Prostaglandins Leukot Essent Fatty Acids. 1991 Nov;44(3):149-54. [PubMed:1808624 ]
  9. Fuse S, Tomita H, Chiba S: Plasma thromboxane B2 concentration in patients with ventricular septal defect and pulmonary hypertension. Jpn Circ J. 1998 Mar;62(3):193-7. [PubMed:9583446 ]
  10. Tewes KS, Tsikas D, Gutzki FM, Frolich JC: Measurement of thromboxane B2 in platelet-rich human plasma by gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry following extractive pentafluorobenzyl esterification. Anal Biochem. 1998 Jul 15;261(1):121-4. [PubMed:9683522 ]
  11. de Meijer A, Vollaard H, de Metz M, Verbruggen B, Thomas C, Novakova I: Meloxicam, 15 mg/day, spares platelet function in healthy volunteers. Clin Pharmacol Ther. 1999 Oct;66(4):425-30. [PubMed:10546927 ]
  12. Mistakopulo NF, Shoshiashvili VD, Saltanov AI, Kushlinskii NE, Ivshina AV, Madzhuga AI, Liakina LT, Ukrainets AM, Zabotina TN, Kadagidze ZG: [The effect of indomethacin and leukinferon on the level of blood plasma thromboxane B2, platelet aggregation and the immune system of patients with endometrial cancer in the perioperative period] Anesteziol Reanimatol. 1992 Mar-Apr;(2):14-8. [PubMed:1416192 ]
  13. Fuse S, Kamiya T: Plasma thromboxane B2 concentration in pulmonary hypertension associated with congenital heart disease. Circulation. 1994 Dec;90(6):2952-5. [PubMed:7994842 ]


General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:
Uniprot ID:
Molecular weight: