Ouabain

Details

• Internal ID: d61f0a49-7d9a-4268-a286-8126e50a4d55
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(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-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): 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
• SMILES (Isomeric): 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=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
• InChI Key: LPMXVESGRSUGHW-HBYQJFLCSA-N
• Popularity: 26,268 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₂
• Molecular Weight: 584.70 g/mol
• Exact Mass: 584.28327683 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.51
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• G-Strophanthin
• Ouabaine
• Acocantherin
• Uabanin
• Oubain
• Purostrophan
• Gratus strophanthin
• Ouabain anhydrous
• 630-60-4
• Astrobain
• Gratibain
• Ouabain octahydrate
• Acocantherine
• Quabain
• Ouabagenin-L-rhamnosid
• Strophanthin-G
• Strophalen
• Kombetin
• Ouabagenin L-rhamnoside
• Strodival
• Uabaina
• Ouabain, Octahydrate
• Rectobaina
• Solufantina
• Strophoperm
• Strophosan
• G-Strophicor
• Strophanthin G
• Ouabagenin-L-rhamnosid [German]
• CHEBI:472805
• G-Strophanthin (JAN)
• UNII-5ACL011P69
• MLS000069786
• CHEMBL222863
• DTXSID0043765
• NSC-25485
• 5ACL011P69
• Acolongifloroside K
• C29H44O12.8H2O
• Strophantin-g
• SMR000058492
• Quabain octahydrate
• O 3125
• G-STROPHANTHIN [JAN]
• 3-(alpha-L-rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide
• 5-18-05-00625 (Beilstein Handbook Reference)
• Card-20(22)-enolide, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-, (1.beta.,3.beta.,5.beta.,11.alpha.)-
• CCRIS 965
• OBN
• DTXCID8023765
• HSDB 3519
• EINECS 211-139-3
• Ouabain (anhydrous)
• NSC 25485
• Cardiac glycoside
• BRN 0101712
• 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
• CAS-630-60-4
• SR-01000076047
• C29-H44-O12.8H2-O
• Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxy-, (1beta,3beta,5beta,11alpha)-
• 1ibg
• 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11alpha,14,19-pentahydroxycard-20(22)-enolide
• 3-(6-Deoxy-alpha-L-mannopyranosyloxy)-1,5,11a,14,19-pentahydroxycard-20(22)-enolide
• C29-H44-O12
• NCGC00163473-01
• 3-[(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-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXY-, (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-
• 3a3y
• Opera_ID_395
• OUABAIN [MI]
• Card-20(22)-enolide, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-, octahydrate, (1.beta.,3.beta.,5.beta.,11.alpha.)-
• OUABAIN [MART.]
• Prestwick0_000471
• Prestwick1_000471
• Prestwick2_000471
• Prestwick3_000471
• OUABAIN [WHO-DD]
• D0AR3J
• Epitope ID:161502
• G-STROPHANTHIN [MI]
• Lopac0_000943
• SCHEMBL15433
• BSPBio_000602
• SPBio_002541
• OUABAIN [EP MONOGRAPH]
• BPBio1_000664
• cid_439501
• GTPL4826
• OUABAIN ANHYDROUS [HSDB]
• REGID_for_CID_439501
• 3n23
• HMS2089J19
• HMS2235A07
• HMS3262N08
• (1-beta,3-beta,5-beta,11-alpha)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide
• Tox21_110024
• Tox21_112057
• Tox21_301547
• Tox21_500943
• BDBM50286739
• HB1140
• AKOS024285581
• Tox21_112057_1
• CCG-205024
• CCG-208243
• DB01092
• LP00943
• SDCCGSBI-0050917.P002
• SMP1_000142
• NCGC00013319-01
• NCGC00015769-17
• NCGC00015769-32
• NCGC00017394-02
• NCGC00017394-07
• NCGC00017394-11
• NCGC00255970-01
• NCGC00261628-01
• NCGC00263656-01
• EU-0100943
• C01443
• D00112
• EN300-19631221
• Q285911
• SR-01000721848
• SR-01000076047-1
• SR-01000076047-5
• SR-01000721848-2
• SR-01000721848-4
• BRD-K35708212-331-03-1
• 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11alpha,14,19-pentahydoxycard-20(22)-enolide
• (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXYCARD-20(22)-ENOLIDE
• 3-[(6-Deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11.alpha.,14,19-pentahydroxycard-20(22)-enolide
• 4-((1R,3S,5S,8R,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-tetrahydro-2H-pyran-2-yloxy)-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• 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-methyltetrahydro-2H-pyran-2-yl)oxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• 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-tetrahydro-2H-pyran-2-yloxy)-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• 4-((1R,3S,5S,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-methyltetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• 4-[(1R,3aS,3bR,5aS,7S,9R,9aR,9bS,10R,11aR)-3a,5a,9,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one
• 4-[(1R,3S,5S,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-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
• 4-[(R)-1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
• 4-[1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
• 4-[1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one(Ouabain)
• Ouabain4-[1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8248	82.48%
Caco-2	-	0.8744	87.44%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8382	83.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.7846	78.46%
CYP3A4 substrate	+	0.7236	72.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.9242	92.42%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5246	52.46%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9343	93.43%
Skin irritation	-	0.5648	56.48%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6927	69.27%
skin sensitisation	-	0.9189	91.89%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7525	75.25%
Acute Oral Toxicity (c)	I	0.8357	83.57%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	-	0.6075	60.75%
Glucocorticoid receptor binding	+	0.5721	57.21%
Aromatase binding	+	0.7113	71.13%
PPAR gamma	+	0.5574	55.74%
Honey bee toxicity	-	0.7156	71.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9498	94.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	63.1 nM; 125.9 nM; 50.1 nM; 63.1 nM; 50.1 nM; 50.1 nM	Potency; Potency; Potency; Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; via CMAUP
CHEMBL1293278	O75496	Geminin	112.2 nM; 112.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	39.8 nM; 100 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293249	Q13887	Kruppel-like factor 5	164.55 nM; 164.55 nM	IC50; IC50	via Super-PRED; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	158.5 nM; 115820.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	100 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	31.6 nM; 794.3 nM; 223.9 nM; 31.6 nM; 316.2 nM; 1122 nM	Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via Super-PRED; via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	125.9 nM; 29092.9 nM; 125.9 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	1154 nM	IC50	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	354.8 nM; 281.8 nM; 100 nM; 223.9 nM; 251.2 nM; 100 nM	Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via Super-PRED; via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM; 501.2 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.80%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.15%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.53%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.33%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.31%	96.77%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.38%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.34%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.32%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.10%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.29%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.77%	97.25%
CHEMBL1871	P10275	Androgen Receptor	88.35%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.77%	92.94%
CHEMBL2581	P07339	Cathepsin D	86.22%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.15%	81.11%
CHEMBL3038469	P24941	CDK2/Cyclin A	85.29%	91.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.54%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.43%	93.04%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.36%	92.88%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.21%	86.00%

Plants that contains it

• Acokanthera oppositifolia
• Acokanthera schimperi
• Arachniodes carvifolia
• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 439501
• NPASS: NPC83287
• ChEMBL: CHEMBL222863
• LOTUS: LTS0236422
• wikiData: Q285911