ContaminantDB: Ouabain

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:49:16 UTC

Update Date

2026-05-14 16:57:45 UTC

Accession Number

CHEM002978

Identification

Common Name

Ouabain

Class

Small Molecule

Description

Ouabain is only found in individuals that have used or taken this drug. It is 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. Ouabain inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Ouabain also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Cardiotonic Agent
Drug
Enzyme Inhibitor
Ester
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(alpha-L-Rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide	ChEBI
g-Strophanthin	ChEBI
Ouabagenin L-rhamnoside	ChEBI
Ouabagenin-L-rhamnosid	ChEBI
Ouabain anhydrous	ChEBI
Ouabaine	ChEBI
Oubain	ChEBI
Strodival	ChEBI
Ouabain octahydrate	Kegg
3-(a-L-Rhamnopyranosyloxy)-1b,5b,11a,14,19-pentahydroxy-5b-card-20(22)-enolide	Generator
3-(Α-L-rhamnopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide	Generator
Ouabain octahydric acid	Generator
Ouabain, octahydrate	HMDB
Strophanthin g	HMDB
Strophanthin-g	HMDB
K, Acolongifloroside	HMDB
Acocantherin	HMDB
Acolongifloroside K	HMDB
g Strophanthin	HMDB

Chemical Formula

C₂₉H₄₄O₁₂

Average Molecular Mass

584.653 g/mol

Monoisotopic Mass

584.283 g/mol

CAS Registry Number

630-60-4

IUPAC Name

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

Traditional Name

ouabain

SMILES

[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

InChI Identifier

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Phenylpropane
Phenylmethylamine
Benzylamine
Aralkylamine
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tertiary amine (CHEBI:3238 )
naphthalenes (CHEBI:3238 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	200°C
Boiling Point	Not Available
Solubility	1.03E+004 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	4.61 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.83 m³·mol⁻¹	ChemAxon
Polarizability	59.93 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-004u-2506409000-f6e6b4b9ec8f6ae25647	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Ouabain,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0001390000-515c0bf892e88276ad0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0fe0-0009610000-dc8e1eef3a28a5855b6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05n0-0109100000-18145b0f69be1294b917	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ap0-0319000000-844262be839a6875a5c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0937000000-d3967c7a1a1193cb4588	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0009510000-d4f2fe6db619b2bc004f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05n0-0109100000-f3754de74f018c89b58b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-002f-3900000000-8897e7140ac63158291a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-05n0-0109100000-821248f465b912b2bcc7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-0319000000-0e7880936c0facd0d79f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-004l-3900000000-89ad74e5219fbfd397f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0fe0-0009610000-8dcd97b10be26bc2f192	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-0937000000-16b6a57d6c5d7d02fcbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-002f-3900000000-7a66faf4065ad077157b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0fe0-0009610000-dc8e1eef3a28a5855b6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0001390000-515c0bf892e88276ad0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-05n0-0109100000-18145b0f69be1294b917	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-0319000000-844262be839a6875a5c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-054o-2900000000-642b0d4e1b611573c54f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-0000490000-ba806aa277f179583eec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0101930000-7f40284ce7a78f730699	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1112910000-f68efe23826a53a2145e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-015i-0000590000-b6bd31b640d6b6350b74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-1101940000-a2d91864bf2df81659a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-2005900000-252c65c11aeae5b683b8	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Ouabain inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Ouabain also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of atrial fibrillation and flutter and heart failure

Minimum Risk Level

Not Available