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Record Information
Version4.0
Creation Date2006-05-22 15:12:18 UTC
Update Date2017-09-27 08:24:18 UTC
HMDB IDHMDB0002904
Secondary Accession Numbers
  • HMDB02904
Metabolite Identification
Common Name2,3-Dinor-TXB2
DescriptionFatty Acyl-Eicosanoid - metabolite of thromboxane. Found to be excreted via urinary tract at a higher level in diabetic rats. A study demonstrates that thromboxane as well as prostacyclin biosynthesis is increased in 2 murine models of atherogenesis and is secondary to increased in vivo platelet activation. Assessment of their generation in these models may afford the basis for future studies on the functional role of these eicosanoids in the evolution and progression of atherosclerosisThromboxanes 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
2,3-Dinor-thromboxaneHMDB
2,3-DinorthromboxaneHMDB
2,3-Dinor TXB2MeSH
2,3-Dinor-thromboxane b2MeSH
Chemical FormulaC18H30O6
Average Molecular Weight342.4272
Monoisotopic Molecular Weight342.204238692
IUPAC Name(3Z)-5-[(2R,3S,4S)-4,6-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl]pent-3-enoic acid
Traditional Name2,3-dinor-thromboxane
CAS Registry Number63250-09-9
SMILES
CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CC(O)=O
InChI Identifier
InChI=1S/C18H30O6/c1-2-3-4-7-13(19)10-11-16-14(8-5-6-9-17(21)22)15(20)12-18(23)24-16/h5-6,10-11,13-16,18-20,23H,2-4,7-9,12H2,1H3,(H,21,22)/b6-5-,11-10+/t13-,14-,15-,16+,18?/m0/s1
InChI KeyRJHNVFKNIJQTQF-LMIBIYGPSA-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
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Oxane
  • Fatty acid
  • Unsaturated fatty acid
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.62 g/LALOGPS
logP2.34ALOGPS
logP2.03ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity91.98 m³·mol⁻¹ChemAxon
Polarizability37.57 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0359000000-5f9e6cceab7c3f7a9cbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-4196000000-fdbaed01f5494e2612fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lkc-9200000000-e8fea20e7b1476c8517dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-0096000000-fe2510f0641448d03e95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-010c-2895000000-da0962ceb32a19fafd35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9550000000-a56f9116ee1c3deadd2fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.011 +/- 0.0012 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.013 +/- 0.002 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023080
KNApSAcK IDNot Available
Chemspider ID4446262
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3829
PubChem Compound5283138
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tsikas D, Gutzki FM, Bohme M, Fuchs I, Frolich JC: Solid- and liquid-phase extraction for the gas chromatographic-tandem mass spectrometric quantification of 2,3-dinor-thromboxane B2 and 2,3-dinor-6-oxo-prostaglandin F1 alpha in human urine. J Chromatogr A. 2000 Jul 14;885(1-2):351-9. [PubMed:10941682 ]
  2. Okumura M, Imanishi M, Okamura M, Hosoi M, Okada N, Konishi Y, Morikawa T, Miura K, Nakatani T, Fujii S: Role for thromboxane A2 from glomerular thrombi in nephropathy with type 2 diabetic rats. Life Sci. 2003 May 2;72(24):2695-705. [PubMed:12679187 ]
  3. Pratico D, Cyrus T, Li H, FitzGerald GA: Endogenous biosynthesis of thromboxane and prostacyclin in 2 distinct murine models of atherosclerosis. Blood. 2000 Dec 1;96(12):3823-6. [PubMed:11090066 ]
  4. Djurup R, Chiabrando C, Jorres A, Fanelli R, Foegh M, Soerensen HU, Joergensen PN: Rapid, direct enzyme immunoassay of 11-keto-thromboxane B2 in urine, validated by immunoaffinity/gas chromatography-mass spectrometry. Clin Chem. 1993 Dec;39(12):2470-7. [PubMed:8252718 ]
  5. Block HU, Sziegoleit W, Mest HJ: Estimation of thromboxane B2 in the clotting human whole blood by gas chromatography. Biomed Biochim Acta. 1984;43(8-9):S385-8. [PubMed:6517904 ]
  6. Aitokallio-Tallberg AM, Jung JK, Kim SJ, Viinikka LU, Ylikorkala RO: Urinary excretion of degradation products of prostacyclin and thromboxane is increased in patients with gestational choriocarcinoma. Cancer Res. 1991 Aug 15;51(16):4146-8. [PubMed:1868436 ]
  7. Foegh ML, Zhao Y, Madren L, Rolnick M, Stair TO, Huang KS, Ramwell PW: Urinary thromboxane A2 metabolites in patients presenting in the emergency room with acute chest pain. J Intern Med. 1994 Feb;235(2):153-61. [PubMed:8308478 ]