Thromboxane B2 (CHEM021688)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:04 UTC
Update Date2026-04-03 02:37:55 UTC
Accession NumberCHEM021688
Identification
Common NameThromboxane B2
ClassSmall Molecule
DescriptionA member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TXB2ChEBI
b2, ThromboxaneHMDB
Chemical FormulaC20H34O6
Average Molecular Mass370.480 g/mol
Monoisotopic Mass370.236 g/mol
CAS Registry Number54397-85-2
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 Namethromboxane B2
SMILESCCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
InChI IdentifierInChI=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 KeyXNRNNGPBEPRNAR-JQBLCGNGSA-N
Chemical Taxonomy
Description 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
  • Long-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Oxane
  • Unsaturated fatty acid
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP3.18ALOGPS
logP2.92ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.18 m³·mol⁻¹ChemAxon
Polarizability42.26 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6y-8898000000-de2ae12c86f74eb4a1f3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00kf-4500079000-16f7d857bfedfb2b9ef2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0911000000-8bc209cb114bb1917b0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-016r-0910000000-7e2600e44fee0ea8636eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0910000000-071d732845973c921adaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0920000000-457ff2b2fc3e77dae9c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-016r-0900000000-949c205efe6ebe79cc8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0900000000-58c0038e67eb610af9dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0900000000-78022e9724d72fe03fc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-2900000000-6141a0015f32b8b88e41Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0690-0900000000-3fc1a2ec184afc048db2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0239000000-9a9e5b4d919679eec445Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-2149000000-4330663714a6c7a5c3c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06du-9210000000-96175166f5a2af4d2062Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016s-0069000000-42550c760b9ebada3323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-11os-3598000000-e17f85b6dd865184b89fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9541000000-f13713eefad69561b2d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0009000000-e9a9bf86af8ea88c1ed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9m-9314000000-acb8a81c85f0c0eeb2c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9400000000-824736787ce880eeebafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-93e9a6bd1728415ca7e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1049000000-e337054bfdddde89caaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-7191000000-c2285e7becd7a28a17fbSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003252
FooDB IDFDB023130
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID422
PDB IDNot Available
Wikipedia LinkThromboxane_B2
Chemspider ID4446261
ChEBI ID28728
PubChem Compound ID5283137
Kegg Compound IDC05963
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24433337
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24786190
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7847191
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. Fuse S, Kamiya T: Plasma thromboxane B2 concentration in pulmonary hypertension associated with congenital heart disease. Circulation. 1994 Dec;90(6):2952-5.