6-[(2R,4R,5S)-2-(2-chlorophenyl)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid

• ChemBase ID: 155027
• Molecular Formular: C22H23ClO5
• Molecular Mass: 402.86802
• Monoisotopic Mass: 402.12340152
• SMILES: c1ccc(c(c1)[C@H]1[C@H](CO[C@H](O1)c1ccccc1Cl)C/C=C\CCC(=O)O)O
• Canonical SMILES: OC(=O)CC/C=C\C[C@H]1CO[C@H](O[C@H]1c1ccccc1O)c1ccccc1Cl
• InChI: InChI=1S/C22H23ClO5/c23-18-11-6-4-9-16(18)22-27-14-15(8-2-1-3-13-20(25)26)21(28-22)17-10-5-7-12-19(17)24/h1-2,4-7,9-12,15,21-22,24H,3,8,13-14H2,(H,25,26)/t15-,21+,22+/m0/s1
• InChIKey: WHUIENZXNGAHQI-ITEAAPOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(2R,4R,5S)-2-(2-chlorophenyl)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid
• IUPAC Traditional name: 6-[(2R,4R,5S)-2-(2-chlorophenyl)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid
• Synonyms: (4Z)-rel-; 4(Z)-6-(2-o-chlorophenyl-4-o-hydroxyphenyl-1,3-dioxan-cis-5-yl) hexenoic acid; 4-Hexenoic acid; 6-[(2R,4R,5S)-2-(2-chlorophenyl)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]-; ICI 192605

Database IDs

• CAS Number: 117621-64-4
• MDL Number: MFCD00673936
• PubChem SID: 162249165
• PubChem CID: 6438399

CALCULATED PROPERTIES

• Acid pKa: 4.0264807
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.6368988
• LogD (pH = 7.4): 1.968539
• Log P: 5.121083
• Molar Refractivity: 107.5745 cm^3
• Polarizability: 41.74702 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H410
• GHS Precautionary statements: P273-P501
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H23ClO5

DETAILS

Sigma Aldrich - I2536

Biochem/physiol Actions
ICI 192605 is a potent thromboxane A2 receptor antagonist. It inhibits platelet aggregation and can reverse the effects of vasoconstrictors such as TXA2 or PGD2. ICI 192605 can reverse vasoconstriction induced by inhibition of NO production by L-NEMA, which leads to an increase in TXA2 release.