dipotassium (3R,4R,5R,6R)-2-{[(1R,4R,5R,7R,9R,10S,13R,15S)-5-carboxy-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecan-7-yl]oxy}-6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]-5-(sulfonatooxy)oxan-4-yl sulfate

• ChemBase ID: 130936
• Molecular Formular: C30H44K2O16S2
• Molecular Mass: 802.98736
• Monoisotopic Mass: 802.13449069
• SMILES: CC(C)CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](OC1O[C@@H]1C[C@H]([C@H]2CC[C@@]34C[C@H](CC[C@H]3[C@@]2(C1)C)C(=C)[C@@H]4O)C(=O)O)CO)OS(=O)(=O)[O-])OS(=O)(=O)[O-].[K+].[K+]
• Canonical SMILES: OC[C@H]1OC(O[C@@H]2C[C@@H](C(=O)O)[C@@H]3[C@](C2)(C)[C@@H]2CC[C@H]4C[C@@]2(CC3)[C@@H](O)C4=C)[C@@H]([C@H]([C@@H]1OS(=O)(=O)[O-])OS(=O)(=O)[O-])OC(=O)CC(C)C.[K+].[K+]
• InChI: InChI=1S/C30H46O16S2.2K/c1-14(2)9-22(32)44-25-24(46-48(39,40)41)23(45-47(36,37)38)20(13-31)43-28(25)42-17-10-18(27(34)35)19-7-8-30-11-16(15(3)26(30)33)5-6-21(30)29(19,4)12-17;;/h14,16-21,23-26,28,31,33H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37,38)(H,39,40,41);;/q;2*+1/p-2/t16-,17-,18-,19-,20-,21+,23-,24+,25-,26+,28?,29-,30-;;/m1../s1
• InChIKey: IUCNQFHEWLYECJ-TUJNHLRFSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: dipotassium (3R,4R,5R,6R)-2-{[(1R,4R,5R,7R,9R,10S,13R,15S)-5-carboxy-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecan-7-yl]oxy}-6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]-5-(sulfonatooxy)oxan-4-yl sulfate
• IUPAC Traditional name: dipotassium (3R,4R,5R,6R)-2-{[(1R,4R,5R,7R,9R,10S,13R,15S)-5-carboxy-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecan-7-yl]oxy}-6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]-5-(sulfonatooxy)oxan-4-yl sulfate
• Synonyms: Atractyloside potassium salt

Database IDs

• CAS Number: 102130-43-8
• MDL Number: MFCD00078810
• PubChem SID: 24891150; 162225214
• PubChem CID: 16218958

CALCULATED PROPERTIES

• Acid pKa: -2.2891104
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): -4.325271
• LogD (pH = 7.4): -5.9470906
• Log P: -1.6925069
• Molar Refractivity: 158.9751 cm^3
• Polarizability: 66.91356 Å^3
• Polar Surface Area: 255.38 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble20 mg/mL

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23/24/25
• Safety Statements: 36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - A6882

Biochem/physiol Actions
An extremely toxic glycoside isolated from thistles. Inhibits oxidative phosphorylation by blocking the transfer of adenosine nucleotides through the mitochondrial membrane.