N-{4-[(2R,4R,6S)-4-{[(diphenyl-1,3-oxazol-2-yl)sulfanyl]methyl}-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl}-N'-hydroxyoctanediamide hydrate

• ChemBase ID: 153251
• Molecular Formular: C41H45N3O8S
• Molecular Mass: 739.8763
• Monoisotopic Mass: 739.29273642
• SMILES: c1ccc(cc1)c1c(oc(n1)SC[C@H]1C[C@H](O[C@H](O1)c1ccc(cc1)NC(=O)CCCCCCC(=O)NO)c1ccc(cc1)CO)c1ccccc1.O
• Canonical SMILES: ONC(=O)CCCCCCC(=O)Nc1ccc(cc1)[C@H]1O[C@@H](CSc2nc(c(o2)c2ccccc2)c2ccccc2)C[C@H](O1)c1ccc(cc1)CO.O
• InChI: InChI=1S/C41H43N3O7S.H2O/c45-26-28-17-19-29(20-18-28)35-25-34(27-52-41-43-38(30-11-5-3-6-12-30)39(51-41)31-13-7-4-8-14-31)49-40(50-35)32-21-23-33(24-22-32)42-36(46)15-9-1-2-10-16-37(47)44-48;/h3-8,11-14,17-24,34-35,40,45,48H,1-2,9-10,15-16,25-27H2,(H,42,46)(H,44,47);1H2/t34-,35+,40+;/m1./s1
• InChIKey: FXNUQEWFGFQQBB-BCQYVYEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(2R,4R,6S)-4-{[(diphenyl-1,3-oxazol-2-yl)sulfanyl]methyl}-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl}-N'-hydroxyoctanediamide hydrate
• IUPAC Traditional name: N-{4-[(2R,4R,6S)-4-{[(diphenyl-1,3-oxazol-2-yl)sulfanyl]methyl}-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl}-N'-hydroxyoctanediamide hydrate
• Synonyms: N1-[4-[(2R,4R,6S)-4-[[(4,5-diphenyl-2-oxazolyl)thio]methyl]-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl]-N8-hydroxy-octanediamide; Tubacin

Database IDs

• CAS Number: 537049-40-4
• PubChem SID: 162247390
• PubChem CID: 71311621

CALCULATED PROPERTIES

• Acid pKa: 8.907536
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 7.520268
• LogD (pH = 7.4): 7.5072083
• Log P: 7.520437
• Molar Refractivity: 201.8303 cm^3
• Polarizability: 80.55252 Å^3
• Polar Surface Area: 143.15 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C41H43N3O7S

DETAILS

Sigma Aldrich - SML0065

Biochem/physiol Actions
Tubacin is a selective inhibitor of histone deacetylase 6 (HDAC6), a predominantly cytoplasmic class II histone deacetylase that is involved in many cellular processes, including degradation of misfolded proteins, cell migration, and cell-cell interaction. Tubacin selectively inhibit HDAC6-mediated alpha -tubulin deacetylation.