Ouabain

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ouabain are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ouabain?

The molecule Ouabain presents a molecular formula of C5H4N4O2 and its IUPAC name is 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.

Ouabain is a natural compound found in the plant Strophanthus gratus, which is native to Africa. It is a white, crystalline substance with a bitter taste and a pungent smell. Ouabain has been used for centuries in traditional medicine to treat a variety of ailments, including heart conditions and hypertension..

Ouabain has a number of medicinal properties, including cardiovascular effects. It is commonly used to treat heart conditions, such as heart failure and atrial fibrillation, by increasing the force of contraction of the heart muscle and increasing the heart rate. It is also used to treat hypertension, or high blood pressure, by constricting the blood vessels and increasing blood pressure..

Ouabain has been studied for its potential therapeutic benefits in a number of conditions, including stroke, diabetes, and cancer. It has been shown to have antioxidant and anti-inflammatory properties and may be useful in the treatment of these and other conditions..

Ouabain is available in the form of a supplement and can be taken orally or applied topically to the skin. It is generally well-tolerated, but it can cause side effects in some people, including nausea, vomiting, and dizziness. It may also interact with certain medications, such as blood thinners and blood pressure medications, so it is important to inform your healthcare provider of all medications you are taking..

Summary

From all the above, this molecule is a natural compound found in the plant Strophanthus gratus that has a number of medicinal properties, including cardiovascular effects. It is commonly used to treat heart conditions and hypertension and has been studied for its potential therapeutic benefits in a number of conditions. Ouabain is available in the form of a supplement and can be taken orally or applied topically to the skin. It is generally well-tolerated, but it can cause side effects in some people and may interact with certain medications. It is important to inform your healthcare provider of all medications you are taking before taking ouabain..

3D structure

Cartesian coordinates

Geometry of Ouabain in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Ouabain LRFVTYWOQMYALW-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Ouabain

 

Molecule descriptors

 
IUPAC name3-[(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
InChI codeInChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
InChI KeyLRFVTYWOQMYALW-UHFFFAOYSA-N
SMILESO=c1[nH]c(=O)c2[nH]cnc2[nH]1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXYCARD-20(22)-ENOLIDE
  • (1alpha,3beta,5beta,11alpha,17alpha)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide
  • 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
  • 3-(alpha-L-rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide
  • 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
  • 3-[(6-Deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11.alpha.,14,19-pentahydroxycard-20(22)-enolide
  • 3a3y
  • 3n23
  • 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,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-[(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
  • 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)
  • 5ACL011P69
  • 630-60-4
  • Acocantherin
  • Acocantherine
  • Astrobain
  • BDBM50286739
  • BPBio1_000664
  • BRN 0101712
  • BSPBio_000602
  • C01443
  • 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.)-
  • CCG-205024
  • CCG-208243
  • CCRIS 965
  • Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxy-, (1beta,3beta,5beta,11alpha)-
  • 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.)-
  • Cardiac glycoside
  • D00112
  • DB01092
  • DSSTox_CID_23765
  • DSSTox_GSID_43765
  • DSSTox_RID_80072
  • EU-0100943
  • Epitope ID:161502
  • G-Strophanthin
  • G-Strophanthin (JAN)
  • G-Strophicor
  • GTPL4826
  • Gratibain
  • Gratus strophanthin
  • HMS2089J19
  • HMS2235A07
  • HMS3262N08
  • HSDB 3519
  • Kombetin
  • LP00943
  • Lopac0_000943
  • MLS000069786
  • NCGC00013319-01
  • NCGC00015769-17
  • NCGC00015769-32
  • NCGC00017394-02
  • NCGC00017394-07
  • NCGC00017394-11
  • NCGC00163473-01
  • NCGC00255970-01
  • NCGC00261628-01
  • NCGC00263656-01
  • NSC 25485
  • NSC-25485
  • O 3125
  • OBN
  • Opera_ID_395
  • Ouabagenin L-rhamnoside
  • Ouabagenin-L-rhamnosid
  • Ouabain
  • Ouabain anhydrous
  • Ouabain octahydrate
  • Ouabain, Octahydrate
  • 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
  • Ouabaine
  • Oubain
  • Prestwick0_000471
  • Prestwick1_000471
  • Prestwick2_000471
  • Prestwick3_000471
  • Purostrophan
  • Q285911
  • Quabain
  • REGID_for_CID_439501
  • Rectobaina
  • SDCCGSBI-0050917.P002
  • SMP1_000142
  • SMR000058492
  • SR-01000076047
  • SR-01000076047-1
  • SR-01000076047-5
  • SR-01000721848
  • SR-01000721848-2
  • SR-01000721848-4
  • Solufantina
  • Strodival
  • Strophalen
  • Strophanthin-G
  • Strophantin-g
  • Strophoperm
  • Strophosan
  • Uabaina
  • Uabanin
  • cid_439501
  • ouabain

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC8143614
  • CAS-630-60-4
  • UNII-5ACL011P69
  • AKOS024285581
  • BRD-K35708212-331-03-1
  • DTXSID0043765
  • CHEMBL222863
  • CHEBI:472805
  • Tox21_110024
  • Tox21_112057
  • Tox21_301547
  • Tox21_500943
  • Tox21_112057_1
  • EINECS 211-139-3
  • SPBio_002541
  • SCHEMBL15433

Physico-Chemical properties

IUPAC name3-[(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
Molecular formulaC5H4N4O2
Molecular weight152.111
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity37.34
LogP-1.1
Topological polar surface area94.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.