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Term:ouabain
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Accession:CHEBI:472805 term browser browse the term     term annotations  view annotations
Definition:A multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+(/K)+)-ATPase (sodium pump).
Synonyms:exact_synonym: 3-(6-deoxy-alpha-L-mannopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide
 related_synonym: 3-(alpha-L-rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide;   C29H44O12;   G-Strophanthin;   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;   Ouabagenin L-Rhamnoside;   Ouabagenin-L-rhamnosid;   Ouabain anhydrous;   Ouabaine;   Oubain;   Strodival;   [H][C@@]12CC[C@]3(O)C[C@H](C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]1(C)[C@H](CC[C@]21O)C1=CC(=O)OC1)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
 alt_id: CHEBI:44461;   CHEBI:7805
 xref_casrn: 630-60-4
 xref: Beilstein:101712 "Beilstein Registry Number";   ChEMBL:472805 "ChEMBL COMPOUND";   ChemIDplus:630-60-4 "CAS Registry Number";   CiteXplore:10438974 "PubMed citation";   DrugBank:DB01092 "DrugBank";   KEGG COMPOUND:630-60-4 "CAS Registry Number";   KEGG COMPOUND:C01443 "KEGG COMPOUND";   KEGG DRUG:D00112 "KEGG DRUG"
 xref_mesh: MESH:D010042
 xref: PDBeChem:OBN "PDBeChem"
Parent Terms Term With Siblings Child Terms
(17Z)-protosta-17(20),24-dien-3beta-ol
(24R)-11alpha,20,24-trihydroxyecdysone
(24R)-24-methylcycloart-25-en-3beta-ol
(25R)-11alpha,20,26-trihydroxyecdysone
(25S)-11alpha,20,26-trihydroxyecdysone
(2R,3S,2'R)-nadolol + 
(S)-timolol (anhydrous) + 
(S)-timolol hemihydrate
(S)-timolol maleate
(Z)-24-ethylidenelophenol
11alpha-hydroxyprogesterone +
11beta,17alpha,21-trihydroxypregnenolone
12-O-acetyldigoxin
16,17-didehydropregnenolone
16-O-acetylgitoxin
16alpha-hydroxydehydroepiandrosterone
16alpha-hydroxypregnenolone
17alpha,21-dihydroxypregnenolone
17alpha-hydroxypregnenolone 
17beta-estradiol + 
17beta-hydroxy-17-methylestra-4,9,11-trien-3-one 
17beta-hydroxy-5alpha-androstan-3-one 
19-hydroxytestosterone
2,22,25-trideoxyecdysone
2-(4-hydroxyphenyl)ethanol + 
2-deoxyecdysone
2-hydroxy-17beta-estradiol 
2-methoxy-17beta-estradiol + 
2-O-alpha-L-rhamnosyl-alpha-L-rhamnosyl-3-hydroxydecanoyl-3-hydroxydecanoic acid
20,22-dihydrodigoxigenin
21-hydroxypregnenolone
24-methylidenelophenol
25-deoxyecdysone
3'''-O-acetyldigitoxin
3,21-dioxoolean-18-en-28-oic acid
3-epi-digoxigenin
3beta,6beta-dihydroxy-5beta-cholan-24-oic acid
3beta-hydroxy-4alpha-methyl-5alpha-cholest-7-ene-4beta-carboxylic acid
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylic acid
3beta-hydroxy-5alpha-cholest-8(14)-en-15-one 
3beta-hydroxy-5alpha-cholestan-15-one
3beta-hydroxy-5beta-pregnan-20-one
3beta-hydroxysteroid dehydrogenase inhibitor +
3beta-sterol + 
4-aminobutyrate transaminase inhibitor + 
4-aminofolic acid
4-carboxy-4-methylzymosterol
4-methylzymosterol
4alpha-methyl-5alpha-cholest-7-en-3beta-ol
4beta-(hydroxymethyl)-4alpha-methyl-5alpha-cholest-7-en-3beta-ol
5,6alpha-epoxy-5alpha-cholestan-3beta-ol 
5,6beta-epoxy-5alpha-cholestan-3beta-ol
5,6beta-epoxy-5beta-cholestan-3beta-ol
5-enolpyruvylshikimate-3-phosphate synthase inhibitor +
5alpha-androstane-3beta,17alpha-diol
5alpha-androstane-3beta,17beta-diol
5alpha-cholest-8(14)-en-3beta,15beta-diol
5alpha-cholestan-3beta,15beta-diol
5alpha-cholestane-3beta,5,6beta-triol
5alpha-reductase inhibitor + 
5beta-androstane-3beta,17beta-diol
6,7-didehydro-17beta-estradiol
6-dehydrotestosterone +
6-deoxoteasterone
6-deoxycathasterone
6-methoxyluteolin 7-alpha-L-rhamnoside
6beta-hydroxytestosterone 
7,8-didehydro-17beta-estradiol
9-fluoro-17-methyl-5beta-androstane-3alpha,11beta,17beta-triol
acebutolol 
acebutolol hydrochloride
acetohydroxyacid synthase inhibitor +
acetyl-CoA carboxylase inhibitor +
acetylcholinesterase inhibitor + 
acetylstrophanthidin
acid ceramidase inhibitor + 
acid--amino-acid ligase inhibitor + 
aconitase inhibitor +
acovenoside A
acyl-CoA:cholesterol acyltransferase inhibitor +
adenosine + 
adenosine deaminase inhibitor + 
adonitoxigenin +
adonitoxin
affinity label +
agigenin +
ajugalactone
alcohol dehydrogenase inhibitor + 
alcohol oxidase inhibitor + 
aldehyde dehydrogenase inhibitor + 
aldose reductase inhibitor + 
alkaline phosphatase inhibitor + 
alpha-amylase inhibitor + 
alpha-glucosidase inhibitor + 
alpha-glucoside hydrolase inhibitor + 
alpha-L-Rhap-(1->2)-[alpha-L-Rhap-(1->2)-alpha-D-Galp-(1->3)-beta-D-GlcpNAc-(1->4)]-alpha-L-Rhap-(1->2)-alpha-L-Rhap-(1->1')-[alpha-L-Rhap-(1->3')]-D-glucitol
alpha-L-Rhap-(1->3)-D-glucitol
alpha-L-Rhap-(1->3)-D-ribitol
alpha-L-Rhap-(1->4)-D-ribitol
alprenolol + 
anabolic androgenic steroid + 
anaplastic lymphoma kinase inhibitor +
androgen + 
androst-5-ene-3beta,17beta-diol 
androstane-3alpha,17beta-diol +
angiotensin-converting enzyme inhibitor + 
antiogenin +
antioside
arachidonoylethanolamide amidohydrolase inhibitor +
arbutamine
arginine decarboxylase inhibitor +
arogenate dehydrogenase inhibitor +
aromatase inhibitor + 
aromatic-L-amino-acid decarboxylase inhibitor + 
astilbin
atenolol + 
atovaquone
atropine + 
bafilomycin A1 
beclomethasone dipropionate
benzaldehyde 
bepridil + 
beta-lactamase inhibitor + 
betamethasone + 
betamethasone valerate 
bevantolol + 
bevantolol hydrochloride +
bipindogenin +
bisoprolol + 
boldenone 
bretylium +
bretylium tosylate
bucladesine 
bufalin 
C21-steroid hormone + 
Ca(2+)-transporting ATPase inhibitor + 
calotropone
cannogenin +
carbachol 
carbonic anhydrase inhibitor + 
carnitine palmitoyltransferase-1 inhibitor + 
carteolol 
carteolol hydrochloride
castanospermine
catechol O-methyltransferase inhibitor +
cathasterone +
cellulose synthesis inhibitor + 
chitin synthase inhibitor +
cholinesterase inhibitor + 
chymotrypsin inhibitor +
cinalukast
circumdatin H
clidinium +
clidinium bromide
coagulation factor Xa inhibitor +
convallasaponin A
convallatoxin
corticosteroid hormone + 
cyasterone
cyclooxygenase inhibitor + 
cyclopropane fatty acid synthase inhibitor + 
cystathionine-beta-synthase inhibitor + 
cytochrome c oxidase inhibitor
cytochrome P450 17-alpha-hydroxylase/C17,20-lyase inhibitor +
danazol 
dehydroepiandrosterone + 
Delta(1)-dihydrotestosterone
desipramine + 
deslanoside
desogestrel 
diacylglycerol O-acyltransferase inhibitor
diamine oxidase inhibitor
diazoxide 
dicoumarol 
dienogest 
diginatigenin +
diginatin
digitalin
digitogenin +
digitoxigenin + 
digitoxigenin 3-O-[beta-D-glucosyl-(1->4)-alpha-L-acofrioside]
digitoxin + 
digoxigenin + 
digoxigenin 3,12-diacetate
digoxigenin monodigitoxoside
digoxin + 
dihydrodigitoxin
dihydrofolate reductase inhibitor + 
dihydroorotate dehydrogenase inhibitor + 
dihydropteroate synthetase inhibitor +
dipeptidase inhibitor +
disopyramide + 
DNA adenine methyltransferase inhibitor + 
DNA ligase (ATP) inhibitor
DNA polymerase inhibitor + 
DNA synthesis inhibitor + 
dobutamine + 
dobutamine hydrochloride
dofetilide 
dopamine + 
EI-1511-5
EI-1625-2
elaeodendroside U
elaeodendroside V
elaeodendroside W
electron-transport chain inhibitor + 
encainide +
encainide hydrochloride
enprofylline
epiandrosterone
erysimoside
erythromycin estolate 
esculeogenin A
esmolol +
esmolol hydrochloride
esomeprazol + 
estramustine + 
estriol + 
estriol 3-O-(beta-D-glucuronide) 
estrogen + 
ethacrynic acid 
ethynodiol +
etonogestrel 
evomonoside
farnesyl pyrophosphate synthetase inhibitor + 
fatty acid synthase inhibitor + 
fatty acid synthesis inhibitor + 
felodipine 
fluoxymesterone 
fosmidomycin
fructose-bisphosphatase inhibitor + 
fulvestrant 
fusidic acid 
gemcitabine +
gemcitabine hydrochloride
geranylgeranyl diphosphate synthase inhibitor +
geranylgeranyltransferase type I inhibitor +
gitaloxin
gitoxigenin +
gitoxigenin 3-acetate
gitoxin +
glucosylceramidase inhibitor + 
glucosylceramide synthase inhibitor +
glutamate synthase inhibitor +
glutaminase inhibitor +
glutamine synthetase inhibitor +
glyburide 
glyceraldehyde-3-phosphate dehydrogenase inhibitor +
glycinamide ribonucleotide formyltransferase inhibitor + 
glycoside hydrolase inhibitor + 
glycyphyllin
golgi alpha-mannosidase II inhibitor +
halosterol B
hellebrigenin +
heparanase inhibitor
histone deacetylase inhibitor + 
HIV-1 integrase inhibitor +
HIV-1 RNase H inhibitor +
HPPD inhibitor +
hydroxymethylglutaryl-CoA reductase inhibitor + 
hydroxypregnenolone + 
indoleamine 2,3-dioxygenase inhibitor +
inokosterone
inosine monophosphate dehydrogenase inhibitor + 
inositol phosphorylceramide synthase inhibitor +
isoprenaline 
kidjoranin-3-O-alpha-diginopyranosyl-(1->4)-beta-cymaropyranoside
kidjoranin-3-O-beta-digitoxopyranoside
L-rhamnosyl-3-hydroxydecanoyl-3-hydroxydecanoic acid
leukocyte elastase inhibitor +
levonorgestrel 
levosimendan
lidocaine + 
lidocaine hydrochloride +
lidocaine hydrochloride monohydrate
lipid kinase inhibitor + 
lipoxygenase inhibitor + 
lokundjoside
losartan 
magnesium sulfate + 
makisterone B
matrix metalloproteinase inhibitor +
mestranol 
metholone +
methyltestosterone 
metipranolol 
metipranolol hydrochloride
metolazone
metyrapone 
mexiletine + 
mexiletine hydrochloride
microbial collagenase inhibitor +
milrinone 
monoamine oxidase inhibitor + 
montelukast + 
moricizine + 
moricizine hydrochloride
mytatrienediol
N-acetylglucosamine phosphotransferase inhibitor + 
N-acetylprocainamide
N-acetylserotonin methyltransferase inhibitor +
Na(+)/K(+)-transporting ATPase inhibitor +
NAD(P)H:quinone oxidoreductase inhibitor + 
nadolol 
NADPH oxidase inhibitor + 
nandrolone + 
neoastilbin
neriifolin
nitisinone 
nitric oxide synthase inhibitor + 
norethisterone 
O-propanoyl-L-carnitine
O-propanoylcarnitine +
oleandrigenin
oleandrigenin monodigitoxoside
oleandrin
oligo-1,6-glucosidase inhibitor + 
ortho-iodosylbenzoic acid
ouabagenin
ouabain 
A multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+(/K)+)-ATPase (sodium pump).
oxandrolone
oxolinic acid
P450 inhibitor + 
palmitic acid + 
penicillin binding protein 3 inhibitor + 
pennogenin +
peptidase inhibitor + 
peptide deformylase inhibitor +
phenylalanine ammonia-lyase inhibitor +
phenylephrine + 
phosphatidylinositol-specific phospholipase C inhibitor + 
phosphodiesterase inhibitor + 
phospholipase A2 inhibitor + 
phosphonopyruvate hydrolase inhibitor +
phosphoprotein phosphatase inhibitor + 
phytoene dehydrogenase inhibitor + 
pimobendan 
podecdysone B
poly(ADP-ribose) polymerase inhibitor + 
polypodine B
ponasterone A 
poststerone
practolol 
pregnenolone + 
procainamide + 
procainamide hydrochloride
propafenone 
propafenone hydrochloride
propranolol + 
protease inhibitor + 
protein farnesyltransferase inhibitor + 
protein kinase inhibitor + 
protein serine/threonine phosphatase inhibitor + 
protein synthesis inhibitor + 
protein tyrosine phosphatase inhibitor +
proton pump inhibitor + 
purine nucleoside phosphorylase inhibitor + 
pyrimidine synthesis inhibitor + 
quinidine + 
retinoic acid synthase inhibitor + 
reverse transcriptase inhibitor + 
rhodexin A
riboflavin synthetase inhibitor +
RNA polymerase inhibitor + 
sarmentogenin +
scillaren A
scillarenin +
serine endopeptidase inhibitor + 
serine hydroxymethyltransferase inhibitor + 
serine palmitoyltransferase inhibitor + 
shidasterone
sialyltransferase inhibitor +
Sir2 inhibitor + 
sotalol 
sotalol hydrochloride
sphingosine N-acyltransferase inhibitor +
squalene monooxygenase inhibitor +
sterol methyltransferase inhibitor +
strophanthidin +
strospeside
sucrose alpha-glucosidase inhibitor + 
sulmazole
tankyrase inhibitor +
teasterone +
testosterone + 
thioredoxin reductase inhibitor + 
thrombin inhibitor + 
thymidylate synthase inhibitor + 
tibolone 
tirucalla-7,24-dien-3beta-ol
tocainide
tomatidine +
topoisomerase inhibitor + 
transglutaminase-2 inhibitor +
triacylglycerol lipase inhibitor + 
trilostane
tryptophan synthase inhibitor +
tyrosinase inhibitor + 
tyrosine 3-monooxygenase inhibitor +
urease inhibitor + 
valproic acid + 
verapamil + 
voriconazole
xanthine oxidase inhibitor + 
zanamivir
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