OBN

OUABAIN

Created:	1999-07-08
Last modified:	2011-06-04

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9 entries where OBN is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	85
Chiral Atom Count	15
Bond Count	90
Aromatic Bond Count	0

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Chemical Component Summary
Name	OUABAIN
Systematic Name (OpenEye OEToolkits)	4-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
Formula	C₂₉ H₄₄ O₁₂
Molecular Weight	584.652
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C1OCC(=C1)C4CCC5(O)C3CCC6(O)CC(OC2OC(C(O)C(O)C2O)C)CC(O)C6(CO)C3C(O)CC45C
SMILES	CACTVS	3.341	C[CH]1O[CH](O[CH]2C[CH](O)[C]3(CO)[CH]4[CH](O)C[C]5(C)[CH](CC[C]5(O)[CH]4CC[C]3(O)C2)C6=CC(=O)OC6)[CH](O)[CH](O)[CH]1O
SMILES	OpenEye OEToolkits	1.5.0	CC1C(C(C(C(O1)OC2CC(C3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
Canonical SMILES	CACTVS	3.341	C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
InChI	InChI	1.03	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	InChI	1.03	LPMXVESGRSUGHW-HBYQJFLCSA-N

Drug Info: DrugBank

DrugBank ID	DB01092
Name	Ouabain
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.
Synonyms	G-Strophanthin Ouabaine Ouabagenin L-Rhamnoside Oubain Ouabain anhydrous 3-(α-L-rhamnopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide Ouabain Ouabagenin-L-rhamnosid
Indication	For the treatment of atrial fibrillation and flutter and heart failure
Categories	Carbohydrates Cardanolides Cardenolides Cardiac Glycosides Cardiac Therapy Cardiotonic Agents Cardiovascular Agents Compounds used in a research, industrial, or household setting Enzyme Inhibitors Fused-Ring Compounds Glycosides OAT3/SLC22A8 Inhibitors OATP1B1/SLCO1B1 Inhibitors OATP1B1/SLCO1B1 Substrates OATP1B3 substrates Protective Agents Steroids Strophanthins Strophanthus Glycosides
ATC-Code	C01AC01
CAS number	630-60-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium/potassium-transporting ATPase subunit alpha-1	MGKGVGRDKYEPAAVSEQGDKKGKKGKKDRDMDELKKEVSMDDHKLSLDE...	unknown	inhibitor
Sodium/potassium-transporting ATPase subunit alpha-2	MGRGAGREYSPAATTAENGGGKKKQKEKELDELKKEVAMDDHKLSLDELG...	unknown	inhibitor
Sodium/potassium-transporting ATPase subunit alpha-3	MGDKKDDKDSPKKNKGKERRDLDDLKKEVAMTEHKMSVEEVCRKYNTDCV...	unknown	inhibitor
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	substrate,inhibitor
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	inhibitor
Solute carrier organic anion transporter family member 4C1	MKSAKGIENLAFVPSSPDILRRLSASPSQIEVSALSSDPQRENSQPQELQ...	unknown	substrate
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	substrate
Solute carrier organic anion transporter family member 1C1	MDTSSKENIQLFCKTSVQPVGRPSFKTEYPSSEEKQPCCGELKVFLCALS...	unknown	substrate
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	substrate,inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682