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

• ChemBase ID: 134200
• Molecular Formular: C20H34O6
• Molecular Mass: 370.48036
• Monoisotopic Mass: 370.23553881
• SMILES: CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC(O1)O)O)C/C=C\CCCC(=O)O)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]hept-5-enoic acid
• IUPAC Traditional name: thromboxane B2
• Synonyms: TXB2; Thromboxane B2; (5Z,9α,11RS,13E,15S)-9,11,15-Trihydroxythromboxa-5,13-dien-1-oic acid; Thromboxane B2; 8-(1-Hydroxy-3-oxopropyl)-9,12-dihydroxy-5,10-heptadecadienoic Acid Hemiacetal; (5Z,9α,13E,15S)9,11,15-Trihydroxythromboxa-5,13-dien-1-oic Acid; (5Z)-7-[(2R,3S,4S)-Tetrahydro-4,6-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]-2H-pyran-3-yl]-5-heptenoic Acid

Database IDs

• CAS Number: 54397-85-2
• MDL Number: MFCD00135258
• PubChem SID: 162228477; 24899894
• PubChem CID: 5283137

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

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 85-87°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - T0516

Biochem/physiol Actions
Prostaglandin derivative that is released during anaphylaxis; induces arterial contraction and platelet aggregation. Review of endogenous thromboxane B2 in risk analysis for development of thrombogenic disorders.1

Toronto Research Chemicals - T405600

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 11-dehydro TBX2 (D230555)

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)