5-alpha-Dihydrotestosterone glucuronide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 5-alpha-Dihydrotestosterone glucuronide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 5-alpha-Dihydrotestosterone glucuronide?

The molecule 5-alpha-Dihydrotestosterone glucuronide presents a molecular formula of C7H15Cl2N2O2P and its IUPAC name is (2S,3S,4S,5R,6R)-6-[[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

5-alpha-Dihydrotestosterone glucuronide (5α-DHTG) is a molecule that is produced in the body when testosterone is metabolized by the enzyme 5α-reductase. 5α-DHTG is a potent androgen that has been shown to bind to androgen receptors with high affinity and to stimulate androgen receptor signaling. 5α-DHTG is also a potent agonist of the G protein-coupled receptor 30 (GPR30), which is thought to be involved in the regulation of cell proliferation and differentiation. 5α-DHTG has been shown to stimulate proliferation of prostate cancer cells and to promote the growth of facial and body hair in men..

3D structure

Cartesian coordinates

Geometry of 5-alpha-Dihydrotestosterone glucuronide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

5-alpha-Dihydrotestosterone glucuronide CMSMOCZEIVJLDB-CQSZACIVSA-N chemical compound 2D structure molecule svg
5-alpha-Dihydrotestosterone glucuronide

 

Molecule descriptors

 
IUPAC name(2S,3S,4S,5R,6R)-6-[[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI codeInChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)/t14-/m1/s1
InChI KeyCMSMOCZEIVJLDB-CQSZACIVSA-N
SMILESO=[P@]1(N(CCCl)CCCl)NCCCO1

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.

  • (2S,3S,4S,5R,6R)-6-[[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  • (5alpha,17beta)-3-oxoandrostan-17-yl beta-D-glucopyranosiduronic acid
  • .BETA.-D-GLUCOPYRANOSIDURONIC ACID, (5.ALPHA.,17.BETA.)-3-OXOANDROSTAN-17-YL
  • 17.BETA.-HYDROXY-5.ALPHA.-ANDROSTAN-3-ONE GLUCURONIDE
  • 17beta-hydroxy-5alpha-androstan-3-one glucuronide
  • 2VVB2958E5
  • 3-oxo-5alpha-androstan-17beta-yl beta-D-glucopyranosiduronic acid
  • 42037-24-1
  • 5-a-Dihydrotestosterone glucuronide
  • 5-alpha-ANDROSTAN-17-beta-OL-3-ONE GLUCOSIDURONATE
  • 5-alpha-Dihydrotestosterone glucuronide
  • 5.ALPHA.-DIHYDROTESTOSTERONE GLUCURONIDE
  • 5.ALPHA.-DIHYDROTESTOSTERONE-O-GLUCURONIDE
  • 5alpha-Dihydrotestosterone glucuronide
  • 5alpha-dihydrotestosterone 17-(beta-D-glucuronide)
  • 5alpha-dihydrotestosterone 17-O-(beta-D-glucuronic acid)
  • 5alpha-dihydrotestosterone 17-O-(beta-D-glucuronide)
  • 5alpha-dihydrotestosterone 17-beta-glucuronide
  • 5alpha-dihydrotestosterone-17G
  • Dihydrotestosterone 17-Glucuronide
  • Dihydrotestosterone glucuronide
  • LMST05010041
  • Q27161610
  • Stanolone glucuronate
  • stanolone 17-glucuronide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC40164488
  • DTXSID801305053
  • CHEBI:89417

Physico-Chemical properties

IUPAC name(2S,3S,4S,5R,6R)-6-[[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC7H15Cl2N2O2P
Molecular weight261.086
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity62.60
LogP2.2
Topological polar surface area51.4

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.