3-ethyl-2-[3-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)prop-1-en-1-yl]-1,3-benzothiazol-3-ium iodide

• ChemBase ID: 153909
• Molecular Formular: C23H25IN2S
• Molecular Mass: 488.42747
• Monoisotopic Mass: 488.07831781
• SMILES: CC[n+]1c2ccccc2sc1/C=C/C=C\1/C(c2ccccc2N1C)(C)C.[I-]
• Canonical SMILES: CC[n+]1c(/C=C/C=C/2\N(C)c3c(C2(C)C)cccc3)sc2c1cccc2.[I-]
• InChI: InChI=1S/C23H25N2S.HI/c1-5-25-19-13-8-9-14-20(19)26-22(25)16-10-15-21-23(2,3)17-11-6-7-12-18(17)24(21)4;/h6-16H,5H2,1-4H3;1H/q+1;/p-1
• InChIKey: TWBRXRGFFUATNI-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-2-[3-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)prop-1-en-1-yl]-1,3-benzothiazol-3-ium iodide
• IUPAC Traditional name: 3-ethyl-2-[3-(1,3,3-trimethylindol-2-ylidene)prop-1-en-1-yl]-1,3-benzothiazol-3-ium iodide
• Synonyms: 2-[3-(1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-3-ethyl-benzothiazolium iodide; AC-93253 iodide; AC-93253

Database IDs

• CAS Number: 108527-83-9
• MDL Number: MFCD03769029
• PubChem SID: 162248048; 24724406
• PubChem CID: 56845487

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5483102
• LogD (pH = 7.4): 1.5484195
• Log P: 1.5484208
• Molar Refractivity: 124.6955 cm^3
• Polarizability: 43.906986 Å^3
• Polar Surface Area: 7.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: dark purple solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H25N2SI

DETAILS

Sigma Aldrich - A9605

Biochem/physiol Actions
AC-93253 is a potent, cell permeable, subtype selective RAR (RARα) agonist. EC50 = 6.3 μM. AC-93253 has high selectivity; 89% for RARα vs 67% for RARβ1, 35% for RARβ2, and 11% for RARγ.