4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 175948
• Molecular Formular: C29H44O12
• Molecular Mass: 584.65246
• Monoisotopic Mass: 584.28327685
• SMILES: C1[C@@H](C[C@@]2([C@]([C@@H]1O)([C@@H]1[C@@H](CC2)[C@@]2([C@](C[C@H]1O)([C@H](CC2)C1=CC(=O)OC1)C)O)CO)O)O[C@H]1[C@H](C([C@H](C(O1)C)O)O)O
• Canonical SMILES: OC[C@@]12[C@H](O)C[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1[C@H](O)C[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@@H]1OC(C)[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13?,15-,16+,17+,18+,19+,21+,22-,23?,24-,25-,26+,27-,28+,29-/m0/s1
• InChIKey: LPMXVESGRSUGHW-KFIIUWQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-5H-furan-2-one
• Synonyms: (1β,3β,5β,11α)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide Octahydrate; g-Strophanthin Octahydrate; Ouabain Octahydrate

Database IDs

• CAS Number: 11018-89-6
• PubChem SID: 164231858
• PubChem CID: 71232391

CALCULATED PROPERTIES

• Acid pKa: 7.181447
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -2.7907462
• LogD (pH = 7.4): -3.204898
• Log P: -2.781806
• Molar Refractivity: 140.8338 cm^3
• Polarizability: 56.89489 Å^3
• Polar Surface Area: 206.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 90-92°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O714500

A cardiac glycoside that inhibits Na(+)/K(+) ATPase. It regulates transcription of MDR (increase, Pgp) and MRP (increase MRP1 and decrease CFTR, cyctic fibrosis transport receptor or cAMP-activated Cl- channel) genes, also alters localization of MRP1.

REFERENCES

• Padilha, A.S. et al.: Clin. Exp. Pharmacol. Physiol., 35, 801 (2008)
• Blaustein, M.P. et al.: Clin. Exp. Hypertens. 20, 691 (2008)
• van Huysse, J.W. et al.: Clin. Exp. Hypertens. 20, 657 (2008)