LIPID MAPS

Structure Database (LMSD)

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Common Name

TXB2-d4

Systematic Name

9S,11,15S-trihydroxy-thromboxa-5Z,13E-dien-1-oic acid-d4

Synonyms

Thromboxane B2-d4

LM ID

LMFA03030010

Formula

C₂₀H₃₀D₄O₆

Exact Mass

Calculate m/z

374.260648

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Thromboxane B2-d4 (TXB2-d4) is intended for use as an internal standard for the quantification of TXB2 by GC- or LC-MS. TXB2 is a non-enzymatically derived, stable, inactive metabolite of TXA2, which is highly unstable.^1,2,3 Serum levels of TXB2 positively correlate with platelet COX-1 activation.^4,5 Urinary levels of TXB2 reflect intrarenal TXA2 synthesis, while its metabolites, 11-dehydro TXB2 and 2,3-dinor TXB2 , reflect systemic TXA2 secretion.^2,6,7

This information has been provided by Cayman Chemical

References

1. Needleman, P., Moncada, S., Bunting, S., et al. Identification of an enzyme in platelet microsomes which generates thromboxane A2 from prostaglandin endoperoxides. Nature 261(5561), 558-560 (1976).

2. Lawson, J.A., Patrono, C., Ciabattoni, G., et al. Long-lived enzymatic metabolites of thromboxane B2 in the human circulation. Anal. Biochem. 155(1), 198-205 (1986).

3. Patrono, C., Ciabattoni, G., Pugliese, F., et al. Estimated rate of thromboxane secretion into the circulation of normal humans. J. Clin. Invest. 77(2), 590-594 (1986).

4. Patrono, C., Ciabattoni, G., Patrignani, P., et al. Evidence for a renal origin of urinary thromboxane B2 in health and disease. Adv. Prostaglandin Thromboxane Leukot. Res. 11, 493-498 (1983).

5. Uyama, O., Matsumoto, M., Fujisawa, A., et al. Plasma concentrations of thromboxane B2 in patients with hypertension or cerebrovascular disease. Prostaglandins Med. 7(3), 199-207 (1981).

6. Arantes, F.B.B., Menezes, F.R., Franci, A., et al. Influence of direct thrombin inhibitor and low molecular weight heparin on platelet function in patients with coronary artery disease: A prospective interventional trial. Adv. Ther. 37(1), 420-430 (2020).

7. Ferroni, P., Riondino, S., Vazzana, N., et al. Biomarkers of platelet activation in acute coronary syndromes. Thromb. Haemost. 108(6), 1109-1123 (2012).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

XNRNNGPBEPRNAR-LCGOHBJFSA-N

InChi (Click to copy)

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/i5D2,8D2

SMILES (Click to copy)

C(O)(=O)CC([2H])([2H])C([2H])([2H])/C=C\C[C@H]1[C@@H](O)CC(O)O[C@@H]1/C=C/[C@@H](O)CCCCC