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

• ChemBase ID: 156114
• 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)/t15-,16-,17-,18+,20?/m0/s1
• InChIKey: XNRNNGPBEPRNAR-YLQJXANPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(2R,3S,4S)-4,6-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(2R,3S,4S)-4,6-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl]hept-5-enoic acid
• Synonyms: (5Z,9α,11RS,13E,15S)-9,11,15-Trihydroxythromboxa-5,13-dien-1-oic acid; TXB2; Thromboxane B2

Database IDs

• CAS Number: 54397-85-2
• MDL Number: MFCD00135258
• PubChem SID: 162250252
• PubChem CID: 71312271

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

Safety Information

• 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

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C20H34O6

DETAILS

Sigma Aldrich - 89227

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