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

• ChemBase ID: 125170
• Molecular Formular: C20H32O6
• Molecular Mass: 368.46448
• Monoisotopic Mass: 368.21988874
• SMILES: O=C1O[C@H](/C=C/[C@@H](O)CCCCC)[C@H]([C@@H](O)C1)C/C=C\CCCC(=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/C20H32O6/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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4-,13-12+/t15-,16-,17-,18+/m0/s1
• InChIKey: KJYIVXDPWBUJBQ-UHHGALCXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid
• IUPAC Traditional name: 11-dehydro-thromboxane
• Synonyms: 11-Dehydro-thromboxane B2; 11-Dehydrothromboxane B2; (5Z)-7-[(2R,3S,4S)-Tetrahydro-4-hydroxy-2-[(1E,3S)-3-hydroxy-1-octen-1-yl]-6-oxo-2H-pyran-3-yl]-5-heptenoic Acid; 11-Dehydro-TXB2; 11-keto-Thromboxane B2; (5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxo-thromboxa-5,13-dien-1-oic Acid; [2R-[2α(1E,3S*),3β(Z),4β]]-7-[Tetrahydro-4-hydroxy-2-(3-hydroxy-1-octenyl)-6-oxo-2H-pyran-3-yl] 5-Heptenoic Acid; 11-Dehydro Thromboxane B2

Database IDs

• CAS Number: 67910-12-7
• PubChem SID: 162219520
• PubChem CID: 5280891
• CHEBI ID: 28667
• Chemspider ID: 4444414
• KEGG ID: C05964
• Wikipedia Title: 11-Dehydrothromboxane_B2

CALCULATED PROPERTIES

• Acid pKa: 4.273003
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.674917
• LogD (pH = 7.4): -0.05771153
• Log P: 2.924771
• Molar Refractivity: 100.2123 cm^3
• Polarizability: 38.903255 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230555

A metabolite of Thromboxane that is an in vivo markers of oxidative stress and platelet activation. It is associated with adverse cardiovascular events in Alzheimer's Disease Anti-inflammatory Prevention Trial (ADAPT).

REFERENCES

• Santilli, F. et al.: J. Am. Coll. Cardiol., 47, 391 (2006)
• Montine, T.J. et al.: PLoS One, 5, No pp given (2006)
• Boehm, E. et al.: J. Biol. Chem., 279, 7663 (2006)