disodium (2R,3R,4R,5R,6R)-6-{[(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}-2-(hydroxymethyl)-5-[(3-methylbutanoyl)oxy]-4-(sulfonatooxy)oxan-3-yl sulfate

• ChemBase ID: 160887
• Molecular Formular: C30H44Na2O16S2
• Molecular Mass: 770.7703
• Monoisotopic Mass: 770.18661589
• SMILES: [C@H]1(C[C@H]([C@@H]2[C@@](C1)([C@H]1[C@]3(CC2)[C@H](C(=C)[C@@H](CC1)C3)O)C)C(=O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)CC(C)C)OS(=O)(=O)[O-])OS(=O)(=O)[O-])CO.[Na+].[Na+]
• Canonical SMILES: OC[C@@H]1O[C@@H](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.[Na+].[Na+]
• InChI: InChI=1S/C30H46O16S2.2Na/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: NFANIWBAUMYKQE-FNAJZLPOSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R,3R,4R,5R,6R)-6-{[(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}-2-(hydroxymethyl)-5-[(3-methylbutanoyl)oxy]-4-(sulfonatooxy)oxan-3-yl sulfate
• IUPAC Traditional name: disodium (2R,3R,4R,5R,6R)-6-{[(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}-2-(hydroxymethyl)-5-[(3-methylbutanoyl)oxy]-4-(sulfonatooxy)oxan-3-yl sulfate
• Synonyms: (2β,4α,15α)-15-Hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-β-D-glucopyranosyl]oxy]-19-norkaur-16-en-18-oic Acid Disodium Salt; Atractylic Acid Disodium Salt; Atractylin Sodium Salt; Sodium Atractylate; Atractyloside Disodium Salt Discontinued

Database IDs

• CAS Number: 100938-11-2
• PubChem SID: 162255022
• PubChem CID: 71313526

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: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 218-220°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A794530

A specific inhibitor of the adenine nucleotide translocase (ANT), which is a mitochondrial ADP/ATP carrier. It is also a proapoptotic ligand of ANT that induces pore formation by ANT, and results in permeabilization of the mitochondria membrane. Studies o

REFERENCES

• Qin, Z.H. et al.: J. Biol. Chem., 276, 8079 (2001)
• Chang, N.S. et al.: J. Biol. Chem., 276, 3361 (2001)
• Ziegler, M. et al.: J. Biol. Chem., 268, 25320 (2001)
• Marzo, I. et al.: Science, 281, 2027 (2001)
• Vieira, H.L. et al.: Cell Death Differ., 7, 1146