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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 15:03:00 UTC
Update Date2017-12-07 01:53:38 UTC
HMDB IDHMDB0004242
Secondary Accession Numbers
  • HMDB04242
Metabolite Identification
Common Name11-Dehydro-thromboxane B2
Description11-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.
Structure
Thumb
Synonyms
ValueSource
11-dehydro-ThromboxaneHMDB
11-dehydro-TXB2HMDB
11-DehydrothromboxaneHMDB
11-Dehydrothromboxane b2HMDB
11-DehydroTXB2HMDB
11-keto-ThromboxaneHMDB
11-keto-Thromboxane b2MeSH
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid
Traditional Name(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid
CAS Registry Number67910-12-7
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/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
InChI KeyKJYIVXDPWBUJBQ-SOGWKEBJSA-N
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
Substituents
  • Thromboxane
  • Long-chain fatty acid
  • Delta valerolactone
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Delta_valerolactone
  • Unsaturated fatty acid
  • Oxane
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

    Element:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 Solubility0.1 g/LALOGPS
logP4ALOGPS
logP2.92ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.21 m³·mol⁻¹ChemAxon
Polarizability41.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-8694000000-b3e1575c156ad43560a4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-3503590000-33e79e5366d8cf9dd7ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0029000000-14e5a0b6b8a0ad2b4202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kh9-3179000000-f322c721c2db5ce99c1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l0m-9040000000-cd3172ac0337835ae861View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0069000000-46a20251644a343285c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05bb-2197000000-44ea48cdcb64f0e36817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9342000000-b6b00743b4251325d4d1View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Platelet
Pathways
NameSMPDB/PathwhizKEGG
Suprofen PathwayPw000258Pw000258 greyscalePw000258 simpleNot Available
Tenoxicam Action PathwayPw000683Pw000683 greyscalePw000683 simpleNot Available
Tiaprofenic Acid Action PathwayPw000682Pw000682 greyscalePw000682 simpleNot Available
Tolmetin Action PathwayPw000681Pw000681 greyscalePw000681 simpleNot Available
Trisalicylate-choline Action PathwayPw000680Pw000680 greyscalePw000680 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00280 +/- 0.00068 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0027 (0.0021-0.0035) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.006 +/- 0.00076 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.01 +/- 0.0015 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0000733 +/- 0.0000266 umol/mmol creatinineAdult (>18 years old)Both
Angina
details
UrineDetected and Quantified0.000165 +/- 0.0000544 umol/mmol creatinineAdult (>18 years old)Both
Angina
details
Associated Disorders and Diseases
Disease References
Angina
  1. 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:1844445 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023347
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05964
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7037
PubChem Compound53477781
PDB IDNot Available
ChEBI ID28667
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:7554708 ]
  2. 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:16400056 ]
  3. 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:12871497 ]
  4. 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:9892587 ]
  5. 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:8443146 ]
  6. 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:8421822 ]
  7. 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:1539506 ]
  8. 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:12135935 ]
  9. 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:7562601 ]
  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:10417625 ]
  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:1632300 ]
  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:15972451 ]
  13. Bohm E, Sturm GJ, Weiglhofer I, Sandig H, Shichijo M, McNamee A, Pease JE, Kollroser M, Peskar BA, Heinemann A: 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. J Biol Chem. 2004 Feb 27;279(9):7663-70. Epub 2003 Dec 10. [PubMed:14668348 ]