(5Z)-7-[(2R,3S,4S)-4,6-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl](3,3,4,4-2H4)hept-5-enoic acid

• ChemBase ID: 178596
• Molecular Formular: C20H34O6
• Molecular Mass: 370.48036
• Monoisotopic Mass: 370.23553881
• SMILES: [C@@H]1(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@H](CCCCC)O)OC(C[C@@H]1O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
• InChI: InChI=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
• InChIKey: XNRNNGPBEPRNAR-JQBLCGNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(2R,3S,4S)-4,6-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl](3,3,4,4-^2H₄)hept-5-enoic acid
• IUPAC Traditional name: thromboxane B2-d4
• Synonyms: 8-(1-Hydroxy-3-oxopropyl)-9,12-dihydroxy-5,10-heptadecadienoic Acid Hemiacetal-d4; (5Z,9α,13E,15S)9,11,15-Trihydroxythromboxa-5,13-dien-1-oic Acid-d4; TXB2-d4; (5Z)-7-[(2R,3S,4S)-Tetrahydro-4,6-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]-2H-pyran-3-yl]-5-heptenoic Acid-d4; Thromboxane B2-d4

Database IDs

• PubChem SID: 164234506
• PubChem CID: 16061116

CALCULATED PROPERTIES

• Acid pKa: 4.273003
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.6731305
• LogD (pH = 7.4): -0.05950255
• Log P: 2.9229848
• Molar Refractivity: 101.1844 cm^3
• Polarizability: 39.44585 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T405602

The labelled analogue of an inactive metabolite/product of Thromboxane A2 (TBXA2): a compound involved in platelet activation and aggregation in case of a wound. Urinary analysis of TXB2 accurately reflects intrarenal TXA2 synthesis while measurement of 1

REFERENCES

• Needleman, P. et al.: Nature, 261, 558 (1976)
• Patrono, C. et al.: J Clin. Invest., 77, 590 (1976)
• Patrono, C. et al.: Adv. Prostaglandin Thromboxane Leukot. Res., 11, 493 (1976)