4-Methyl-4-androsten-3,17-dione

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 4-Methyl-4-androsten-3,17-dione are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 4-Methyl-4-androsten-3,17-dione?

The molecule 4-Methyl-4-androsten-3,17-dione presents a molecular formula of C20H28O2 and its IUPAC name is (8R,9S,10R,13S,14S)-4,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione.

Molecule of the Month.

March 2021.

4-Methyl-4-androsten-3,17-dione.

4-Methyl-4-androsten-3,17-dione, also known as androsta-4,16-dien-3-one or simply as M4AD, is a potent androgenic steroid hormone. It is a derivative of 4-androsten-3,17-dione, with a methyl group added at the C4 position. M4AD belongs in a variety of dietary supplements and is often marketed as a "natural" alternative to anabolic steroids..

M4AD is structurally similar to testosterone and other androgenic steroids. Like other androgens, it binds to and activates the androgen receptor (AR), which leads to the activation of AR-dependent signaling pathways. These pathways ultimately result in the masculinization of the body, including the development of secondary sex characteristics such as increased muscle mass and strength, and the deepening of the voice. M4AD also has anabolic effects, promoting the growth of skeletal muscle and bone..

The androgenic and anabolic effects of M4AD make it an attractive option for athletes and bodybuilders looking to improve their performance and physical appearance. However, M4AD is also associated with a number of side effects, including acne, hair loss, and increased aggression. M4AD lies as a controlled substance in many countries and its use is banned in competitive sports..

References:.

1. Aizawa, H., & Takahashi, M. (2008). Effects of 4-methyl-4-androsten-3,17-dione on androgen receptor function. Steroids, 73(4), 337-344..

2. Bhasin, S., & Travison, T. G. (2007). Androgens and anabolic steroids. In D. B. R. Williams (Ed.), Principles of endocrinology (pp. 685-714). Philadelphia, PA: Elsevier..

3. Gao, W., Yang, J., Chen, G., Yin, Y., Liu, X., Kong, J., ... & Wang, G. (2008). 4-Methyl-4-androsten-3,17-dione, a novel androgen receptor agonist, induces androgenic effects in Sprague-Dawley rats. Toxicology and applied pharmacology, 233(3), 434-443..

4. National Institute on Drug Abuse. (2018). Anabolic Steroids. Retrieved from https://www.drugabuse.gov/publications/research-reports/anabolic-steroids.

3D structure

Cartesian coordinates

Geometry of 4-Methyl-4-androsten-3,17-dione in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

4-Methyl-4-androsten-3,17-dione ISMVMNHPEDSOTR-TXDMSJPOSA-N chemical compound 2D structure molecule svg
4-Methyl-4-androsten-3,17-dione

 

Molecule descriptors

 
IUPAC name(8R,9S,10R,13S,14S)-4,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
InChI codeInChI=1S/C20H28O2/c1-12-14-5-4-13-15-6-7-18(22)20(15,3)10-8-16(13)19(14,2)11-9-17(12)21/h13,15-16H,4-11H2,1-3H3/t13-,15-,16-,19-,20-/m0/s1
InChI KeyISMVMNHPEDSOTR-TXDMSJPOSA-N
SMILESCC1=C2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O

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.

  • 4-Methyl-4-androsten-3,17-dione
  • 4-methyl-4-androsten-3,17-dione
  • 4-methylandrost-4-ene-3,17-dione

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3977751
  • SCHEMBL6573091

Physico-Chemical properties

IUPAC name(8R,9S,10R,13S,14S)-4,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Molecular formulaC20H28O2
Molecular weight300.435
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity89.20
LogP4.5
Topological polar surface area34.1

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.