heptasodium [(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,37R,39R,40R,41R,43R,45R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis[(sulfonatooxy)methyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl sulfate

• ChemBase ID: 169865
• Molecular Formular: C42H63Na7O56S7
• Molecular Mass: 1849.29941
• Monoisotopic Mass: 1847.9410777
• SMILES: [C@H]12O[C@H]3[C@@H]([C@@H]([C@H](O[C@H]3COS(=O)(=O)[O-])O[C@H]3C([C@@H]([C@H](O[C@H]3COS(=O)(=O)[O-])O[C@H]3C([C@@H]([C@H](O[C@H]3COS(=O)(=O)[O-])O[C@H]3[C@@H]([C@@H]([C@H](O[C@H]3COS(=O)(=O)[O-])O[C@H]3C([C@@H]([C@H](O[C@H]3COS(=O)(=O)[O-])O[C@H]3C([C@@H]([C@H](O[C@H]3COS(=O)(=O)[O-])O[C@H]([C@@H](O1)COS(=O)(=O)[O-])C([C@@H]2O)O)O)O)O)O)O)O)O)O)O)O)O)O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: OC1[C@@H]2O[C@H]3O[C@@H](COS(=O)(=O)[O-])[C@H](C([C@@H]3O)O)O[C@H]3O[C@@H](COS(=O)(=O)[O-])[C@H]([C@@H]([C@@H]3O)O)O[C@H]3O[C@@H](COS(=O)(=O)[O-])[C@H](C([C@@H]3O)O)O[C@H]3O[C@H]([C@@H](O[C@H]4O[C@H]([C@@H](O[C@H]5O[C@H]([C@@H](O[C@H]([C@H]1O)O[C@H]2COS(=O)(=O)[O-])C(O)[C@@H]5O)COS(=O)(=O)[O-])[C@H](O)[C@@H]4O)COS(=O)(=O)[O-])C(O)[C@@H]3O)COS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C42H70O56S7.7Na/c43-15-22(50)36-85-8(1-78-99(57,58)59)29(15)92-37-23(51)16(44)31(10(86-37)3-80-101(63,64)65)94-39-25(53)18(46)33(12(88-39)5-82-103(69,70)71)96-41-27(55)20(48)35(14(90-41)7-84-105(75,76)77)98-42-28(56)21(49)34(13(91-42)6-83-104(72,73)74)97-40-26(54)19(47)32(11(89-40)4-81-102(66,67)68)95-38-24(52)17(45)30(93-36)9(87-38)2-79-100(60,61)62;;;;;;;/h8-56H,1-7H2,(H,57,58,59)(H,60,61,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77);;;;;;;/q;7*+1/p-7/t8-,9-,10-,11-,12-,13-,14-,15-,16?,17?,18?,19?,20-,21?,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-;;;;;;;/m1......./s1
• InChIKey: TZBDYIAUDQVKGF-RVUWIZOGSA-G

NAMES AND DATABASE IDS

Names

• IUPAC name: heptasodium [(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,37R,39R,40R,41R,43R,45R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis[(sulfonatooxy)methyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.2^3,^6.2^8,^1^1.2^1^3,^1^6.2^1^8,^2^1.2^2^3,^2^6.2^2^8,^3^1]nonatetracontan-5-yl]methyl sulfate
• IUPAC Traditional name: heptasodium [(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,37R,39R,40R,41R,43R,45R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis[(sulfonatooxy)methyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.2^3,^6.2^8,^1^1.2^1^3,^1^6.2^1^8,^2^1.2^2^3,^2^6.2^2^8,^3^1]nonatetracontan-5-yl]methyl sulfate
• Synonyms: Heptakis(6-O-sulfo)-β-cyclodextrin Heptasodium Salt; 6-O-Sulfo-β-cyclodextrin Sodium Salt; Hs-β-CD

Database IDs

• CAS Number: 197587-31-8
• PubChem SID: 162263997
• PubChem CID: 71317201

CALCULATED PROPERTIES

• Acid pKa: -2.8339024
• H Acceptors: 49
• H Donor: 14
• LogD (pH = 5.5): -28.645718
• LogD (pH = 7.4): -28.645744
• Log P: -24.919851
• Molar Refractivity: 288.9838 cm^3
• Polarizability: 130.98828 Å^3
• Polar Surface Area: 877.45 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Colourless Crystalline Solid
• Melting Point: >210°C (dec)

Safety Information

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

DETAILS

Toronto Research Chemicals - H281125

A β-Cyclodextrin derivative that inhibits anthrax lethal toxin. Chiral selector for capillary electrophorese, CE1.

REFERENCES

• Friedlander, A., et al.: J. Biol. Chem., 261, 7123 (1986)
• Finkelstein, A., et al.: Toxicology, 87, 29 (1986)
• Benson, E., et al.: Biochemistry, 37, 3941 (1986)
• Brossier, F., et al.: Toxicon, 39, 1747 (1986)