(1S,2R,5S,7R,10R,11S,14R,15R)-5-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-15-methyl-14-[5-oxo-2,5-dihydro(2H3)furan-3-yl]tetracyclo[8.7.0.02,7.011,15]heptadecane-2-carbaldehyde

• ChemBase ID: 176279
• Molecular Formular: C30H44O9
• Molecular Mass: 548.66496
• Monoisotopic Mass: 548.29853299
• SMILES: C1[C@@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@@]2([C@](CC1)([C@H](CC2)C1=CC(=O)OC1)C)O)C=O)O[C@@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)OC)O)C
• Canonical SMILES: CO[C@H]1[C@H](O)[C@H](O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C=O)O[C@H]([C@@H]1O)C
• InChI: InChI=1S/C30H44O9/c1-16-24(33)26(36-3)25(34)27(38-16)39-19-6-10-29(15-31)18(13-19)4-5-22-21(29)7-9-28(2)20(8-11-30(22,28)35)17-12-23(32)37-14-17/h12,15-16,18-22,24-27,33-35H,4-11,13-14H2,1-3H3/t16-,18+,19-,20+,21-,22+,24-,25-,26+,27-,28+,29+,30-/m0/s1
• InChIKey: PMTSPAGBAFCORP-HBUONDEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,7R,10R,11S,14R,15R)-5-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-15-methyl-14-[5-oxo-2,5-dihydro(^2H₃)furan-3-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-2-carbaldehyde
• IUPAC Traditional name: (1S,2R,5S,7R,10R,11S,14R,15R)-5-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-15-methyl-14-[5-oxo(^2H₃)furan-3-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-2-carbaldehyde
• Synonyms: (3β,5β)-3-[(6-Deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide-d3; Cannogenin α-L-Thevetoside-d3; Encordin-d3; Peruvosid-d3; Peruvoside-d3

Database IDs

• PubChem SID: 164232189
• PubChem CID: 71751492

CALCULATED PROPERTIES

• Acid pKa: 7.182633
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 2.0107133
• LogD (pH = 7.4): 1.5972767
• Log P: 2.0196319
• Molar Refractivity: 140.0532 cm^3
• Polarizability: 56.244003 Å^3
• Polar Surface Area: 131.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P227572

Labelled Peruvoside (P227570). Peruvoside is a cardiac glycoside with the same inotropic and chronotropic effects on heart function as Ouabain (O714500).

REFERENCES

• Ballica, R., et al.: Biotech. Bioeng., 41, 1075 (1993)
• Chattopadhyay, S., et al.: J. Biosci. Bioeng., 93, 215 (1993)
• Dong, H., et al.: Enzyme Microb. Technol., 31, 116 (1993)