sodium 6-{[(2S,4S,5R,6S,13R,16S,18R)-4-(acetyloxy)-2,6,13,17,17-pentamethyl-6-(4-methylpentyl)-8-oxo-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-1(20)-en-16-yl]oxy}-5-({5-[(4-{[3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-4-hydroxy-6-methyl-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxyoxan-3-yl sulfate

• ChemBase ID: 154767
• Molecular Formular: C60H95NaO29S
• Molecular Mass: 1335.43367
• Monoisotopic Mass: 1334.5577423
• SMILES: CC1C(C(C(C(O1)OC1C(C(COC1O[C@H]1CC[C@]2([C@H](C1(C)C)CC=C1C2CCC23[C@]1(C[C@@H]([C@@H]2[C@](OC3=O)(C)CCCC(C)C)OC(=O)C)C)C)OS(=O)(=O)[O-])O)OC1C(C(C(CO1)O)O)O)O)OC1C(C(C(CO1)O)OC1C(C(C(C(O1)CO)O)OC)O)O.[Na+]
• Canonical SMILES: OCC1OC(OC2C(O)COC(C2O)OC2C(C)OC(C(C2O)OC2OCC(C(C2O)O)O)OC2C(OCC(C2O)OS(=O)(=O)[O-])O[C@H]2CC[C@]3([C@H](C2(C)C)CC=C2C3CCC34[C@@]2(C)C[C@@H]([C@@H]4[C@](OC3=O)(C)CCCC(C)C)OC(=O)C)C)C(C(C1O)OC)O.[Na+]
• InChI: InChI=1S/C60H96O29S.Na/c1-25(2)12-11-17-59(9)49-32(81-27(4)62)20-58(8)29-13-14-35-56(5,6)36(16-18-57(35,7)28(29)15-19-60(49,58)55(72)88-59)83-53-47(39(67)34(24-79-53)89-90(73,74)75)87-54-48(86-50-40(68)37(65)30(63)22-77-50)41(69)44(26(3)80-54)84-51-42(70)45(31(64)23-78-51)85-52-43(71)46(76-10)38(66)33(21-61)82-52;/h13,25-26,28,30-54,61,63-71H,11-12,14-24H2,1-10H3,(H,73,74,75);/q;+1/p-1/t26?,28?,30?,31?,32-,33?,34?,35-,36-,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?,47?,48?,49+,50?,51?,52?,53?,54?,57+,58-,59-,60?;/m0./s1
• InChIKey: JVAXTYZSDXFKMH-RYKXRNEYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 6-{[(2S,4S,5R,6S,13R,16S,18R)-4-(acetyloxy)-2,6,13,17,17-pentamethyl-6-(4-methylpentyl)-8-oxo-7-oxapentacyclo[10.8.0.0^2,^9.0^5,^9.0^1^3,^1^8]icos-1(20)-en-16-yl]oxy}-5-({5-[(4-{[3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-4-hydroxy-6-methyl-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxyoxan-3-yl sulfate
• IUPAC Traditional name: sodium 6-{[(2S,4S,5R,6S,13R,16S,18R)-4-(acetyloxy)-2,6,13,17,17-pentamethyl-6-(4-methylpentyl)-8-oxo-7-oxapentacyclo[10.8.0.0^2,^9.0^5,^9.0^1^3,^1^8]icos-1(20)-en-16-yl]oxy}-5-({5-[(4-{[3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl)oxy]-4-hydroxy-6-methyl-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxyoxan-3-yl sulfate
• Synonyms: Frondoside A hydrate

Database IDs

• CAS Number: 127367-76-4(anhydrous)
• PubChem SID: 162248905
• PubChem CID: 71311967

CALCULATED PROPERTIES

• Acid pKa: -2.000051
• H Acceptors: 26
• H Donor: 10
• LogD (pH = 5.5): -1.801717
• LogD (pH = 7.4): -1.8017385
• Log P: -1.2772856
• Molar Refractivity: 300.8472 cm^3
• Polarizability: 125.00238 Å^3
• Polar Surface Area: 422.86 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C60H95O29S·Na · xH2O

DETAILS

Sigma Aldrich - F0808

Biochem/physiol Actions
Frondoside A is a bioactive triterpenoid saponin from sea cucumber; and an immunostimulant. Frondoside A is an extremely potent inducer of apoptosis, and although it does activate caspaces, it can induce apoptosis in HL-60 cells through a mechanism distinct from extrinsic and intrinsic apoptosis pathways. It potentially valuable for cancers that are resistent to other apoptosis inducers, such as pancreatic cancer.