(2R,3R,4S,5S,6R)-2-(auriosulfanyl)-6-(hydroxymethyl)oxane-3,4,5-triol hydrate

• ChemBase ID: 153860
• Molecular Formular: C6H13AuO6S
• Molecular Mass: 410.19537
• Monoisotopic Mass: 410.00985214
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)S[Au])O)O)O)O.O
• Canonical SMILES: OC[C@H]1O[C@H](S[Au])[C@@H]([C@H]([C@@H]1O)O)O.O
• InChI: InChI=1S/C6H12O5S.Au.H2O/c7-1-2-3(8)4(9)5(10)6(12)11-2;;/h2-10,12H,1H2;;1H2/q;+1;/p-1/t2-,3-,4+,5-,6-;;/m1../s1
• InChIKey: SGVIEHTYEMEDRR-PKXGBZFFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-(auriosulfanyl)-6-(hydroxymethyl)oxane-3,4,5-triol hydrate
• IUPAC Traditional name: aurothioglucose hydrate
• Synonyms: Gold thioglucose; Solganal; Solganol; Aurothioglucose hydrate

Database IDs

• CAS Number: 12192-57-3(anhydrous)
• EC Number: 235-365-7
• PubChem SID: 24724383; 162247999
• PubChem CID: 71311741

CALCULATED PROPERTIES

• Acid pKa: 12.513949
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.2418
• LogD (pH = 7.4): -2.2418034
• Log P: -2.2418
• Molar Refractivity: 41.2457 cm^3
• Polarizability: 24.687445 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (titration)
• Empirical Formula (Hill Notation): C6H11AuO5S · xH2O

DETAILS

Sigma Aldrich - A0606

Biochem/physiol Actions
Aurothioglucose, a gold compound used clinically to treat rheumatoid arthritis, has recently been found to be a potent PKCiota-Par6 interaction inhibitor, with an IC50 approximately 1 μM. Disruption of this interaction disrupts a rac1 signaling pathway that is required for transformed growth in non-small-cell lung cancer.