15-hydroxy-7-{[6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]-4,5-bis(sulfooxy)oxan-2-yl]oxy}-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid sodium

• ChemBase ID: 131382
• Molecular Formular: C30H46NaO16S2
• Molecular Mass: 749.79641
• Monoisotopic Mass: 749.21249667
• SMILES: CC(C)CC(=O)OC1C(C(C(OC1OC1CC(C2CCC34CC(CCC3C2(C1)C)C(=C)C4O)C(=O)O)CO)OS(=O)(=O)O)OS(=O)(=O)O.[Na]
• Canonical SMILES: OCC1OC(OC2CC(C(=O)O)C3C(C2)(C)C2CCC4CC2(CC3)C(O)C4=C)C(C(C1OS(=O)(=O)O)OS(=O)(=O)O)OC(=O)CC(C)C.[Na]
• InChI: InChI=1S/C30H46O16S2.Na/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)
• InChIKey: MWTGRZFZHYKRDI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 15-hydroxy-7-{[6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]-4,5-bis(sulfooxy)oxan-2-yl]oxy}-9-methyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid sodium
• IUPAC Traditional name: 15-hydroxy-7-{[6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]-4,5-bis(sulfooxy)oxan-2-yl]oxy}-9-methyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid sodium
• Synonyms: Atractyloside sodium salt

Database IDs

• CAS Number: 100938-11-2
• MDL Number: MFCD00171231
• PubChem SID: 162225660
• PubChem CID: 71308433

CALCULATED PROPERTIES

• Acid pKa: -2.2891104
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -4.325271
• LogD (pH = 7.4): -5.9470906
• Log P: -1.6925069
• Molar Refractivity: 161.2185 cm^3
• Polarizability: 67.14618 Å^3
• Polar Surface Area: 249.72 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

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: 36/37/39-45
• 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

DETAILS

Sigma Aldrich - A8521

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