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Substance Name: Ouabain
RN: 630-60-4
UNII: 5ACL011P69
InChIKey: LPMXVESGRSUGHW-HBYQJFLCSA-N

Note

  • 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.

Molecular Formula

  • C29-H44-O12

Molecular Weight

  • 584.6546
 

Classification Codes

Classification Codes

  • Cardiotonic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Protective Agents

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 100/10000 lb
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Names and Synonyms

Results Name

  • Ouabain

Name of Substance

  • Ouabain
  • Ouabain anhydrous

MeSH Heading

  • Ouabain

Synonyms

  • 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11alpha,14,19-pentahydroxycard-20(22)-enolide
  • 5-18-05-00625 (Beilstein Handbook Reference)
  • Acocantherin
  • Astrobain
  • BRN 0101712
  • Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxy-, (1beta,3beta,5beta,11alpha)-
  • CCRIS 965
  • EINECS 211-139-3
  • g-Strophanthin
  • g-Strophicor
  • Gratibain
  • Gratus strophanthin
  • HSDB 3519
  • Kombetin
  • NSC 25485
  • Ouabagenin L-rhamnoside
  • Ouabagenin-L-rhamnosid
  • Ouabagenin-L-rhamnosid [German]
  • Ouabain
  • Ouabaine
  • Oubain
  • Purostrophan
  • Quabain
  • Rectobaina
  • Solufantina
  • Strodival
  • Strophalen
  • Strophoperm
  • Strophosan
  • Uabaina
  • Uabanin
  • UNII-5ACL011P69

Systematic Names

  • 3-(6-Deoxy-alpha-L-mannopyranosyloxy)-1,5,11a,14,19-pentahydroxycard-20(22)-enolide
  • Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxy-, (1beta,3beta,5beta,11alpha)-
  • Ouabain

Superlist Name

  • Ouabain

Registry Numbers

CAS Registry Number

  • 630-60-4

FDA UNII

  • 5ACL011P69

Other Registry Number

  • 36-06-6

System Generated Number

  • 0000630604

Structure Descriptors

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

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 100ug/kg (0.1mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965.
cat LD50 intravenous 100ug/kg (0.1mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 35, Pg. 316, 1936.
cat LDLo intraduodenal 820ug/kg (0.82mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958.
cat LDLo oral 5mg/kg (5mg/kg)   Farmacognosia. Vol. 13, Pg. 375, 1953.
cat LDLo subcutaneous 150ug/kg (0.15mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973.
cat LDLo unreported 90ug/kg (0.09mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 471, 1964.
dog LDLo intravenous 54ug/kg (0.054mg/kg) CARDIAC: CHANGE IN RATE Journal of Pharmacology and Experimental Therapeutics. Vol. 179, Pg. 447, 1971.
dog LDLo oral 1500ug/kg (1.5mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
dog LDLo subcutaneous 100ug/kg (0.1mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973.
frog LD50 intravenous 250ug/kg (0.25mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 231, 1965.
frog LD50 parenteral 370ug/kg (0.37mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 995, 1957.
frog LDLo subcutaneous 400ug/kg (0.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973.
guinea pig LD50 intraperitoneal 210ug/kg (0.21mg/kg)   Acta Biologica et Medica Germanica. Vol. 12, Pg. 434, 1964.
guinea pig LD50 intravenous 228ug/kg (0.228mg/kg)   Acta Biologica et Medica Germanica. Vol. 12, Pg. 434, 1964.
guinea pig LD50 oral 8280ug/kg (8.28mg/kg)   United States Patent Document. Vol. #4230702,
guinea pig LD95 intraduodenal 3340ug/kg (3.34mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958.
guinea pig LDLo intraarterial 40ug/kg (0.04mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
guinea pig LDLo intramuscular 220ug/kg (0.22mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 52, Pg. 1, 1934.
guinea pig LDLo subcutaneous 100ug/kg (0.1mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973.
monkey LDLo intravenous 102ug/kg (0.102mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 13, Pg. 412, 1963.
mouse LD50 intracrebral 69ug/kg (0.069mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Pharmacological Research Communications. Vol. 6, Pg. 417, 1974.
mouse LD50 intraperitoneal 11mg/kg (11mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965.
mouse LD50 intravenous 2200ug/kg (2.2mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 118, Pg. 756, 1965.
mouse LD50 oral 5mg/kg (5mg/kg)   Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.
mouse LD50 subcutaneous 5mg/kg (5mg/kg)   Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.
pigeon LDLo intramuscular 330ug/kg (0.33mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909.
pigeon LDLo intravenous 183ug/kg (0.183mg/kg) CARDIAC: CHANGE IN RATE

GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 126, Pg. 412, 1960.
pigeon LDLo oral 14mg/kg (14mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909.
rabbit LD50 intravenous 252ug/kg (0.252mg/kg)   Pharmacological Research Communications. Vol. 13, Pg. 571, 1981.
rabbit LDLo intramuscular 1mg/kg (1mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909.
rabbit LDLo oral 7mg/kg (7mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909.
rabbit LDLo subcutaneous 100ug/kg (0.1mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973.
rat LD50 intravenous 14mg/kg (14mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 44, 1971.
rat LD50 unreported 125mg/kg (125mg/kg)   Toxicology and Applied Pharmacology. Vol. 22, Pg. 336, 1972.
rat LDLo subcutaneous 50mg/kg (50mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 200 deg C   EXP
log P (octanol-water) -2.00E+00 (none)   EXP
Water Solubility 1.03E+04 mg/L 25 EST
Vapor Pressure 6.08E-26 mm Hg 25 EST
Henry's Law Constant 1.77E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.63E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.