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Human Metabolome Database Version 2.5

 

Showing metabocard for 11-Dehydro-thromboxane B2 (HMDB04242)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 16:03:00
Update Date 2009-08-19 14:25:45
Accession Number HMDB04242
Secondary Accession Numbers Not Available
Common Name 11-Dehydro-thromboxane B2
Description 11-Dehydro-thromboxane B2, a stable thromboxane metabolite, is a full agonist of chemoattractant receptor-homologous molecule expressed on TH2 cells (CRTH2) in human eosinophils and basophils. Given its production in the allergic lung, antagonism of the 11-dehydro- thromboxane B2/CRTH2axis may be of therapeutic relevance. (PMID 14668348) 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.
Synonyms
  1. 11-dehydro-thromboxane
  2. 11-dehydrothromboxane
  3. 11-dehydrothromboxane B2
  4. 11-dehydroTXB2
  5. 11-keto-thromboxane
Chemical IUPAC Name 7-[(2S,3S,4S)-4-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-6-oxo-oxan-3-yl]hept-5-enoic acid
Chemical Formula C20H32O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Prostanoids
Sub Class
  • Thromboxanes
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • carboxylic acid ester
  • lactone
  • alkene
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 368.465
Monoisotopic Molecular Weight 368.219879
Isomeric SMILES CCCCC[C@H](O)C=C[C@H]1OC(=O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O
Canonical SMILES CCCCCC(O)C=CC1OC(=O)CC(O)C1CC=CCCCC(O)=O
KEGG Compound ID C05964 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04242 Link Image
Metagene Link HMDB04242 Link Image
METLIN ID 7037 Link Image
PubChem Compound 440862 Link Image
PubChem Substance 11121182 Link Image
ChEBI ID 28667 Link Image
CAS Registry Number 67910-12-7
InChI Identifier InChI=1/C20H32O6/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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4+,13-12+/t15-,16-,17-,18+/m0/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.103 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 4.00 [Predicted by ALOGPS]; 3.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Platelet —
Concentrations (Normal)
Biofluid Blood
Value 0.0027 (0.0021-0.0035) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Reinke M: Monitoring thromboxane in body fluids: a specific ELISA for 11-dehydrothromboxane B2 using a monoclonal antibody. Am J Physiol. 1992 May;262(5 Pt 1):E658-62. [PubMed Link Image]
Biofluid Blood
Value 0.00280 +/- 0.00068 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Oxygenated lipids were quantified by Theresa L. Pedersen and John W. Newman at the USDA’s Western Human Nutrition Research Center, Davis, CA, and Lipomics Technologies, Inc.
References
  • Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. [PubMed Link Image]
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed Link Image]
Biofluid Urine
Value 0.000165 +/- 0.0000544 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Angina
Comments stable angina
References
  • Koike T, Hattori A, Igarashi Y, Matsubara T, Tamura Y, Yamazoe M, Izumi T, Shibata A: [Elevation of 11-dehydro-thromboxane B2 levels in unstable angina] J Cardiol. 1991;21(4):899-904. [PubMed Link Image]
Biofluid Urine
Value 0.006 +/- 0.00076 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Concentrations (Abnormal)
Biofluid Urine
Value 0.0000733 +/- 0.0000266 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Angina
Comments unstable angina
References
  • Koike T, Hattori A, Igarashi Y, Matsubara T, Tamura Y, Yamazoe M, Izumi T, Shibata A: [Elevation of 11-dehydro-thromboxane B2 levels in unstable angina] J Cardiol. 1991;21(4):899-904. [PubMed Link Image]
Biofluid Urine
Value 0.01 +/- 0.0015 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Condition Normal
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition References
Angina
  • Koike T, Hattori A, Igarashi Y, Matsubara T, Tamura Y, Yamazoe M, Izumi T, Shibata A: [Elevation of 11-dehydro-thromboxane B2 levels in unstable angina] J Cardiol. 1991;21(4):899-904. [PubMed Link Image]
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 Link Image]
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
General References
  1. De Cristofaro R, Rocca B, Vitacolonna E, Falco A, Marchesani P, Ciabattoni G, Landolfi R, Patrono C, Davi G: Lipid and protein oxidation contribute to a prothrombotic state in patients with type 2 diabetes mellitus. J Thromb Haemost. 2003 Feb;1(2):250-6. [PubMed Link Image]
  2. Davi G, Ciabattoni G, Consoli A, Mezzetti A, Falco A, Santarone S, Pennese E, Vitacolonna E, Bucciarelli T, Costantini F, Capani F, Patrono C: In vivo formation of 8-iso-prostaglandin f2alpha and platelet activation in diabetes mellitus: effects of improved metabolic control and vitamin E supplementation. Circulation. 1999 Jan 19;99(2):224-9. [PubMed Link Image]
  3. Foulon I, Bachir D, Galacteros F, Maclouf J: Increased in vivo production of thromboxane in patients with sickle cell disease is accompanied by an impairment of platelet functions to the thromboxane A2 agonist U46619. Arterioscler Thromb. 1993 Mar;13(3):421-6. [PubMed Link Image]
  4. Koudstaal PJ, Ciabattoni G, van Gijn J, Nieuwenhuis HK, de Groot PG, Sixma JJ, Patrono C: Increased thromboxane biosynthesis in patients with acute cerebral ischemia. Stroke. 1993 Feb;24(2):219-23. [PubMed Link Image]
  5. Rebuzzi AG, Natale A, Bianchi C, Albanese S, Lanza GA, Coppola E, Ciabattoni G: Importance of reperfusion on thromboxane A2 metabolite excretion after thrombolysis. Am Heart J. 1992 Mar;123(3):560-6. [PubMed Link Image]
  6. Clarke MW, Ward NC, Wu JH, Hodgson JM, Puddey IB, Croft KD: Supplementation with mixed tocopherols increases serum and blood cell gamma-tocopherol but does not alter biomarkers of platelet activation in subjects with type 2 diabetes. Am J Clin Nutr. 2006 Jan;83(1):95-102. [PubMed Link Image]
  7. Cipollone F, Mezzetti A, Porreca E, Di Febbo C, Nutini M, Fazia M, Falco A, Cuccurullo F, Davi G: Association between enhanced soluble CD40L and prothrombotic state in hypercholesterolemia: effects of statin therapy. Circulation. 2002 Jul 23;106(4):399-402. [PubMed Link Image]
  8. Wang Z, Ciabattoni G, Creminon C, Lawson J, Fitzgerald GA, Patrono C, Maclouf J: Immunological characterization of urinary 8-epi-prostaglandin F2 alpha excretion in man. J Pharmacol Exp Ther. 1995 Oct;275(1):94-100. [PubMed Link Image]
  9. Cipollone F, Ganci A, Panara MR, Greco A, Cuccurullo F, Patrono C, Patrignani P: Effects of nabumetone on prostanoid biosynthesis in humans. Clin Pharmacol Ther. 1995 Sep;58(3):335-41. [PubMed Link Image]
  10. Morrow JD, Oates JA, Roberts LJ 2nd, Zackert WE, Mitchell TA, Lazarus G, Guzzo C: Increased formation of thromboxane in vivo in humans with mastocytosis. J Invest Dermatol. 1999 Jul;113(1):93-7. [PubMed Link Image]
  11. Maclouf J, Lellouche F, Martinuzzo M, Said P, Carreras LO: Increased production of platelet-derived thromboxane in patients with lupus anticoagulant. Agents Actions Suppl. 1992;37:27-33. [PubMed Link Image]
  12. Williams PC, Coffey MJ, Coles B, Sanchez S, Morrow JD, Cockcroft JR, Lewis MJ, O'Donnell VB: In vivo aspirin supplementation inhibits nitric oxide consumption by human platelets. Blood. 2005 Oct 15;106(8):2737-43. Epub 2005 Jun 21. [PubMed Link Image]