4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one octahydrate

• ChemBase ID: 102671
• Molecular Formular: C29H60O20
• Molecular Mass: 728.7747
• Monoisotopic Mass: 728.36779432
• SMILES: O=C1OCC(=C1)[C@H]1CC[C@@]2(O)[C@]1(C)C[C@@H](O)[C@H]1[C@H]2CC[C@]2(O)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)C[C@@H](O)[C@]12CO.O.O.O.O.O.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]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O.O.O.O.O.O.O.O.O
• InChI: InChI=1S/C29H44O12.8H2O/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;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1
• InChIKey: TYBARJRCFHUHSN-DMJRSANLSA-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,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one octahydrate; 4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-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 octahydrate
• IUPAC Traditional name: ouabain octahydrate
• Synonyms: G-Strophanthin; Acocantherine; OUABAIN OCTAHYDRATE; 1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside); Ouabain octahydrate

Database IDs

• CAS Number: 11018-89-6
• EC Number: 211-139-3
• MDL Number: MFCD00149240
• Beilstein Number: 101712
• PubChem SID: 24278610; 162089830
• PubChem CID: 6364534

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: ethanol: soluble10 mg/mL; H2O: soluble10 mg/mL (cold); H2O: soluble50 mg/mL (hot)
• Apperance: white powder
• Melting Point: 260°C
• Optical Rotation: [α]25/D -31 to -32.5° in H2O(lit.)
• Absorption Wavelength: ε1mM/220 nm, H2O 15.5

Safety Information

• Storage Condition: 2-8°C, Protect from light
• RTECS: RN3850000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544; 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; II
• Australian Hazchem: 2XE
• Risk Statements: 23/25-33; R:25
• Safety Statements: 45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301 + H331-H373
• GHS Precautionary statements: P261-P301 + P310-P311
• RID/ADR: UN 1544 6.1/PG 1

Pharmacology Properties

• Gene Information: human ... ATIC(471)rat ... Atp1b1(25650)

Product Information

• Purity: ≥95% (HPLC)
• Impurities: ~8 mol/mol water

DETAILS

MP Biomedicals - 02102541

Crystalline
Octahydrate
An inhibitor of sodium-potassium-ion-dependent ATPase.

Sigma Aldrich - O3125

Caution
Aqueous solutions can be autoclaved.
Biochem/physiol Actions
Cardiac glycoside, inhibits Na(+)/K(+) ATPase, 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. Ouabain resistance is associated with appearance of Na(+)/K(+) ATPase isoforms with low binding affinity.

REFERENCES

• J. Pharmacol. Exp. Ther. , 189, 434 (1974).