Calusterone

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

What is the Calusterone?

The molecule Calusterone presents a molecular formula of C21H32O2 and its IUPAC name is (7S,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one.

Calusterone is a molecule that was first isolated from the plant Calotropis gigantea. It is a member of the class of molecules known as sesquiterpene lactones. Calusterone has been shown to have a variety of biological activities, including anticancer, anti-inflammatory, and antifungal activity..

3D structure

Cartesian coordinates

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

2D drawing

 

Calusterone IVFYLRMMHVYGJH-PVPPCFLZSA-N chemical compound 2D structure molecule svg
Calusterone

 

Molecule descriptors

 
IUPAC name(7S,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16-,17-,18+,19-,20-,21-/m0/s1
InChI KeyIVFYLRMMHVYGJH-PVPPCFLZSA-N
SMILESC[C@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O)[C@H]12

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.

  • (1S,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
  • (7S,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
  • (7b,17b)-17-hydroxy-7,17-dimethyl-Androst-4-en-3-one
  • (7beta,8xi,17beta)-17-hydroxy-7,17-dimethylandrost-4-en-3-one
  • 0678G6Q58A
  • 17-.beta.-hydroxy-7-.beta.-17-dimethyl androst-4-en-3-one
  • 17-Hydroxy-7,17-dimethylandrost-4-en-3-one
  • 17-beta-Hydroxy-7-beta,17-alpha-dimethylandrost-4-ene-3-one
  • 17-beta-hydroxy-7-beta-17-dimethyl androst-4-en-3-one
  • 17-dimethyl-17beta-hydroxy-7beta-Androst-4-en-3-one
  • 17.beta.-Hydroxy-7.beta.,17-dimethylandrost-4-en-3-one
  • 17.beta.-Hydroxy-7.beta.,17.alpha.-dimethylandrost-4-ene-3-one
  • 17021-26-0
  • 17b-Hydroxy-7b,17-dimethylandrost-4-en-3-one
  • 17b-hydroxy-7b,17-dimethyl-Androst-4-en-3-one
  • 17beta-Dimethyl testosterone
  • 17beta-Hydroxy-7beta,17-dimethylandrost-4-en-3-one
  • 17beta-Hydroxy-7beta,17alpha-dimethylandrost-4-ene-3-one
  • 17beta-Hydroxy-7beta-17-dimethylandrost-4-en-3-one
  • 17beta-Hydroxy-7beta-17alpha-dimethylandrost-4-ene-3-one
  • 4-Androsten-7-beta, 17-alpha-dimethyl-17-beta-ol-3-one
  • 4-Androsten-7beta,17alpha-dimethyl-17beta-ol-3-one
  • 7-.beta.-17-.alpha.-dimethyltestosterone
  • 7-.beta.-17-dimethyltestosterone
  • 7-beta,17-Dimethyltestosterone
  • 7-beta,17-alpha-Dimethyl testosterone
  • 7-beta-17-alpha-dimethyltestosterone
  • 7.BETA.,17.ALPHA.-DIMETHYL-17.BETA.-HYDROXYANDROST-4-EN-3-ONE
  • 7.beta.,17-Dimethyltestosterone
  • 7.beta.,17.alpha.-Dimethyl testosterone
  • 7.beta.,17.alpha.-Dimethyltestosterone
  • 7beta,17-Dimethyltestosterone
  • 7beta,17alpha-Dimethyl-17betahydroxyandrost-4-en-3-one
  • 7beta,17alpha-Dimethyltestosterone
  • 7beta,17beta-Dimethyltestosterone
  • 7beta-Dimethyltestosterone
  • Androst-4-en-3-one, 17-beta-hydroxy-7-beta,17-dimethyl-
  • Androst-4-en-3-one, 17-hydroxy-7,17-dimethyl-, (7-beta,17-beta)-
  • Androst-4-en-3-one, 17-hydroxy-7,17-dimethyl-, (7beta,17beta)-
  • Androst-4-en-3-one, 17beta-hydroxy-7beta,17-dimethyl-
  • Androst-4-en-3-one, 7-beta,17-alpha-dimethyl-17-beta-hydroxy-
  • Androst-4-en-3-one, 7beta,17alpha-dimethyl-17beta-hydroxy-
  • Androst-4-en-3-one,17-dimethyl-
  • Androst-4-en-3-one,17-dimethyl-, (7.beta.,17.beta.)-
  • Androst-4-en-3-one,17.alpha.-dimethyl-17.beta.-hydroxy-
  • BRN 3212336
  • CALUSTERONE
  • CLS
  • Calusteron
  • Calusterona
  • Calusterone
  • Calusterone (USAN/INN)
  • Calusteronum
  • D03338
  • DB01564
  • Dimethyltestosterone
  • HSDB 3210
  • Methosarb
  • NSC-88536
  • NSC88536
  • Q14201166
  • U 22550
  • U-22,550
  • U-22550
  • WLN: L E5 B666 OV MUTJ A1 E1 FQ F1 K1

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4215173
  • UNII-0678G6Q58A
  • DTXSID0022723
  • CHEMBL455706
  • CHEBI:135356
  • SCHEMBL4509

Physico-Chemical properties

IUPAC name(7S,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Molecular formulaC21H32O2
Molecular weight316.478
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity95.01
LogP4.5
Topological polar surface area37.3

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.