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Record Information
Version3.6
Creation Date2006-05-22 15:12:18 UTC
Update Date2016-02-11 01:05:52 UTC
HMDB IDHMDB02904
Secondary Accession NumbersNone
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
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 KeyInChIKey=RJHNVFKNIJQTQF-LMIBIYGPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentThromboxanes
Alternative Parents
Substituents
  • Thromboxane
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Oxane
  • Saccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity91.98 m3·mol-1ChemAxon
Polarizability37.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB02904
Metagene LinkHMDB02904
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. [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. [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. [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. [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. [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. [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. [8308478 ]