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^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 963
• Molecular Formular: C29H44O12
• Molecular Mass: 584.65246
• Monoisotopic Mass: 584.28327685
• SMILES: O[C@@]12[C@H]3[C@@H]([C@@]4([C@](O)(CC3)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)C[C@H]4O)CO)[C@H](O)C[C@@]1([C@H](CC2)C1=CC(=O)OC1)C
• 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
• 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-HBYQJFLCSA-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^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 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
• IUPAC Traditional name: ouabain
• Brand Name: Acocantherin; Astrobain; G-Strophicor; Gratibain; Gratus Strophanthin; Kombetin; Purostrophan; Rectobaina; Solufantina; Strodival; Strophalen; Strophoperm; Strophosan; Uabaina; Uabanin
• Synonyms: Ouabain Octahydrate; Ouabain, Octahydrate; Ouabaine; G-Strophanthin; Ouabagenin L-Rhamnoside; Strophanthin G; Strophanthin-G; Ouabain

Database IDs

• CAS Number: 630-60-4
• PubChem SID: 160964426; 46505479
• PubChem CID: 439501
• CHEBI ID: 472805
• ATC CODE: C01AC01
• CHEMBL: 447086
• Chemspider ID: 388599
• DrugBank ID: DB01092
• KEGG ID: D00112
• Unique Ingredient Identifier: 5ACL011P69
• Wikipedia Title: Ouabain

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -1.03
• LOG S: -2.1
• Solubility (Water): 4.61e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.03E+004 mg/L
• Hydrophobicity(logP): -1.2

DETAILS

MP Biomedicals - 05218018

MP Biomedicals Rare Chemical collection

DrugBank - DB01092

• Drug Groups: approved
• Description: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like digitalis. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-exchanging ATPase. [PubChem]
• Indication: For the treatment of atrial fibrillation and flutter and heart failure
• Pharmacology: Ouabain, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.
• Affected Organisms: Humans and other mammals
• Protein Binding: 60%
• References: Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. [Pubmed] ; Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. [Pubmed] ; Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. [Pubmed] ; Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. [Pubmed] ; Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. Pubmed
• Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. Pubmed
• Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. Pubmed
• Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. Pubmed
• Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. Pubmed