4-{[(4S,5R)-1-carboxy-4-hydroxynonadeca-6,8,10,13-tetraen-5-yl]sulfanyl}benzoic acid

• ChemBase ID: 155765
• Molecular Formular: C27H36O5S
• Molecular Mass: 472.63674
• Monoisotopic Mass: 472.22834525
• SMILES: CCCCC/C=C/C/C=C/C=C/C=C/[C@H]([C@H](CCCC(=O)O)O)Sc1ccc(cc1)C(=O)O
• Canonical SMILES: CCCCC/C=C/C/C=C/C=C/C=C/[C@H]([C@H](CCCC(=O)O)O)Sc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C27H36O5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(28)15-14-17-26(29)30)33-23-20-18-22(19-21-23)27(31)32/h6-7,9-13,16,18-21,24-25,28H,2-5,8,14-15,17H2,1H3,(H,29,30)(H,31,32)/t24-,25+/m0/s1
• InChIKey: PKJINWOACFYDQN-LOSJGSFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(4S,5R)-1-carboxy-4-hydroxynonadeca-6,8,10,13-tetraen-5-yl]sulfanyl}benzoic acid
• IUPAC Traditional name: 4-{[(4S,5R)-1-carboxy-4-hydroxynonadeca-6,8,10,13-tetraen-5-yl]sulfanyl}benzoic acid
• Synonyms: 6(R)-(4-Carboxyphenylthio)-5(S)-hydroxy-7(E),9(E),11(E),14(Z)-eicosatetraenoic acid; Bay u9773

Database IDs

• CAS Number: 134733-55-4
• MDL Number: MFCD00898723
• PubChem SID: 162249903; 24892151
• PubChem CID: 71312218

CALCULATED PROPERTIES

• Acid pKa: 3.795969
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 4.1276326
• LogD (pH = 7.4): 0.75481695
• Log P: 6.7735696
• Molar Refractivity: 140.8182 cm^3
• Polarizability: 52.692802 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >25 mg/mL; ethanol: >25 mg/mL
• Apperance: white oil

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -70°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C27H36O5S

DETAILS

Sigma Aldrich - B9680

Biochem/physiol Actions
Subtype-selective cysteinyl-leukotriene (Cys-Lt) antagonist.