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Record Information
Version3.6
Creation Date2006-05-22 15:12:44 UTC
Update Date2014-08-05 20:16:53 UTC
HMDB IDHMDB03252
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.
Structure
Thumb
Synonyms
  1. TXB2
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
SMILES
CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,20-22,25H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4-,13-12+/t15-,16-,17-,18+,20?/m0/s1
InChI KeyXNRNNGPBEPRNAR-JQBLCGNGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassThromboxanes
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Heterocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Hemiacetal
  • Oxane
  • 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
  • Extracellular
  • Membrane (predicted from logP)
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 Solubility0.25ALOGPS
logP3.18ALOGPS
logP2.92ChemAxon
logS-3.2ALOGPS
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
Spectra
SpectraNot 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
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00019 +/- 0.00007 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.00041 +/- 0.00018 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.00554 +/- 0.00235 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.01080 +/- 0.00370 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.48196 +/- 0.14576 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0214 +/- 0.0409 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000865 +/- 0.00018 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.95 +/- 0.24 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000919 +/- 0.0016 uMAdult (>18 years old)Not Specified
Normal
details
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.027 +/- 0.048 uMAdult (>18 years old)Both
Ischemic heart disease
details
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
Normal
  1. Farker K, Schweer H, Vollandt R, Nassr N, Nagel U, Seyberth HW, Hoffmann A, Oettel M: Measurements of urinary prostaglandins in young ovulatory women during the menstrual cycle and in postmenopausal women. Prostaglandins. 1997 Sep;54(3):655-64. Pubmed: 9373880
  2. Viinikka L, Ylikorkala O: Measurement of thromboxane B2 in human plasma or serum by radioimmunoassay. Prostaglandins. 1980 Oct;20(4):759-66. Pubmed: 7465865
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
METLIN ID422
PubChem Compound5283137
PDB IDNot Available
ChEBI ID28728
References
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

Transporters

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:
SLCO2B1
Uniprot ID:
O94956
Molecular weight:
76697.9