Human Metabolome Database Version 3.5

Showing metabocard for Thromboxane B2 (HMDB03252)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:44 -0600
Update Date 2013-02-08 17:12:23 -0700
HMDB ID HMDB03252
Secondary Accession Numbers
  • HMDB05070
Metabolite Identification
Common Name Thromboxane B2
Description Thromboxanes. 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. TXB2
Chemical Formula C20H34O6
Average Molecular Weight 370.4804
Monoisotopic Molecular Weight 370.23553882
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 IUPAC Name thromboxane B2
CAS Registry Number 54397-85-2
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 Key XNRNNGPBEPRNAR-JQBLCGNGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Thromboxanes
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Heterocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Hemiacetal
  • Oxane
  • 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
  • Extracellular
  • Membrane (predicted from logP)
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 0.25 g/L ALOGPS
LogP 3.18 ALOGPS
LogP 2.92 ChemAxon
LogS -3.18 ALOGPS
pKa (strongest acidic) 4.27 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 107.22 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 101.18 ChemAxon
Polarizability 42.26 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Epidermis
  • Prostate
  • Adipose Tissue
  • Lung
  • Nerve Cells
  • Platelet
  • Spleen
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
0.00019 +/- 0.00007 uM Adult (>18 years old) Female Comment Normal
Blood Detected and Quantified
0.00041 +/- 0.00018 uM Adult (>18 years old) Female Comment Normal
Blood Detected and Quantified
0.00554 +/- 0.00235 uM Adult (>18 years old) Female Comment Normal
Blood Detected and Quantified
0.01080 +/- 0.00370 uM Adult (>18 years old) Female Comment Normal
Blood Detected and Quantified
0.48196 +/- 0.14576 uM Adult (>18 years old) Female Comment Normal
Blood Detected and Quantified
0.0214 +/- 0.0409 uM Adult (>18 years old) Both Comment Normal
Blood Detected and Quantified
0.865 +/- 0.18 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.95 +/- 0.24 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.919 +/- 1.6 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
3.7E-5 +/- 7E-6 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.00085 +/- 0.00015 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.0024 +/- 0.00094 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.0526 (0.0395-0.0658) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.027 +/- 0.048 uM Adult (>18 years old) Both Comment Ischemic heart disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000267 uM Children (1-13 year old) Not Specified closed head
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00220 (0.000583-0.00451) uM Children (1-13 year old) Not Specified closed head
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00264 uM Children (1-13 year old) Not Specified gunshot wound
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000107 uM Not Specified Not Specified HIV-Seropositive, Dementia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000467 +/- 0.000243 uM Not Specified Not Specified hydrocephalus
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00172 (0.000945-0.00248) uM Children (1-13 year old) Not Specified hypoxic/ischemic
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00289 (0.000594-0.00711) uM Children (1-13 year old) Not Specified meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0117 +/- 0.00177 uM Not Specified Not Specified subarachnoid hemorrhage with cerebral vasospasm
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0155 +/- 0.00243 uM Not Specified Not Specified subarachnoid hemorrhage without cerebral vasospasm
Cerebrospinal Fluid (CSF) Detected and Quantified 3.322e-05 uM Not Specified Not Specified HIV-Seropositive (Neurologically normal)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000032 +/- 0.00001 uM Adult (>18 years old) Both Intracranial tumours
Associated Disorders and Diseases
Disease References
Brain tumors
  • 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 Link_out
      Ischemic heart disease
      • 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 Link_out
          Normal
          • 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 Link_out
          • Viinikka L, Ylikorkala O: Measurement of thromboxane B2 in human plasma or serum by radioimmunoassay. Prostaglandins. 1980 Oct;20(4):759-66. Pubmed: 7465865 Link_out
              Associated OMIM IDs None
              DrugBank ID Not Available
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB023130
              KNApSAcK ID Not Available
              Chemspider ID 4446261 Link_out
              KEGG Compound ID C05963 Link_out
              BioCyc ID Not Available
              BiGG ID Not Available
              Wikipedia Link Thromboxane B2 Link_out
              NuGOwiki Link HMDB03252 Link_out
              Metagene Link HMDB03252 Link_out
              METLIN ID 422 Link_out
              PubChem Compound 5283137 Link_out
              PDB ID Not Available
              ChEBI ID 28728 Link_out
              References
              Synthesis Reference Not Available
              Material Safety Data Sheet (MSDS) Download (PDF)
              General References
              1. 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 Link_out
              2. 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 Link_out
              3. 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 Link_out
              4. 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 Link_out
              5. 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 Link_out
              6. 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 Link_out
              7. 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 Link_out
              8. 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 Link_out
              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 Link_out
              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 Link_out
              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 Link_out
              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 Link_out
              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 Link_out

              Transporters
              Name: Solute carrier organic anion transporter family member 2B1
              Reactions: Not Available
              Gene Name: SLCO2B1
              Uniprot ID: O94956 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA