(1S,2S,5S,10R,11S,14R,15R)-5-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-2-carbaldehyde

• ChemBase ID: 179885
• Molecular Formular: C34H48O14
• Molecular Mass: 680.73652
• Monoisotopic Mass: 680.30440622
• SMILES: [C@@]12([C@@]([C@@H](C3=CC(=O)OC3)CC2)(CC[C@@H]2[C@@]3(C(=C[C@@H](O[C@H]4[C@@H]([C@H]([C@H](O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CO4)O)O)CC3)CC[C@@H]12)C=O)C)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@H]2CC[C@]3(C(=C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C=O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C34H48O14/c1-32-7-5-20-21(34(32,43)9-6-19(32)16-10-24(37)44-13-16)3-2-17-11-18(4-8-33(17,20)15-36)46-30-28(41)26(39)23(14-45-30)48-31-29(42)27(40)25(38)22(12-35)47-31/h10-11,15,18-23,25-31,35,38-43H,2-9,12-14H2,1H3/t18-,19+,20-,21+,22+,23+,25+,26-,27-,28+,29+,30-,31-,32+,33+,34-/m0/s1
• InChIKey: HFXNSSUZFCOFIY-XOHMQVQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,10R,11S,14R,15R)-5-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-2-carbaldehyde
• IUPAC Traditional name: (1S,2S,5S,10R,11S,14R,15R)-5-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-2-carbaldehyde
• Synonyms: Securidaside; Hyrcanoside

Database IDs

• CAS Number: 15001-93-1
• PubChem SID: 164235795
• PubChem CID: 10055345

CALCULATED PROPERTIES

• Acid pKa: 7.1826286
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -1.0694963
• LogD (pH = 7.4): -1.4829395
• Log P: -1.0605774
• Molar Refractivity: 163.9925 cm^3
• Polarizability: 66.00956 Å^3
• Polar Surface Area: 221.9 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Na-K ATPase inhibitor

Product Information

• Biological Source: Constit. of Coronilla hyrcana and Securigera securidaca
• Application(s): Cardiant; Cardioglycoside

REFERENCES

• Bagirov, R.B. et al., Khim. Prir. Soedin., 1966, 2, 251; Chem. Nat. Compd. (Engl. Transl.), 1966, 2, 202, (isol)
• Hemlrec, J.A. et al., J. Nat. Prod., 1979, 42, 293, (isol)
• Zatula, V.V. et al., Khim. Prir. Soedin., 1965, 1, 153; 1966, 2, 438; 1969, 5, 127; 128; Chem. Nat. Compd. (Engl. Transl.), 1965, 1, 117; 1966, 2, 359; 1969, 5, 110; 111, (isol, struct)