Amorolfina

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

What is the Amorolfina?

The molecule Amorolfina presents a molecular formula of C21H35NO and its IUPAC name is (2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine.

Amorolfina is a molecule that was first isolated from the fungus Amorpha niger. This molecule has been shown to have antifungal activity against a variety of pathogenic fungi, including Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans. Amorolfina has also been shown to have antibacterial activity against Gram-positive bacteria, such as Staphylococcus aureus. In addition, Amorolfina has been shown to have anticancer activity against a variety of cancer cell lines, including breast, colon, and lung cancer cells..

3D structure

Cartesian coordinates

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

2D drawing

 

Amorolfina MQHLMHIZUIDKOO-OKZBNKHCSA-N chemical compound 2D structure molecule svg
Amorolfina

 

Molecule descriptors

 
IUPAC name(2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine
InChI codeInChI=1S/C21H35NO/c1-7-21(5,6)20-10-8-19(9-11-20)12-16(2)13-22-14-17(3)23-18(4)15-22/h8-11,16-18H,7,12-15H2,1-6H3/t16-,17-,18+/m0/s1
InChI KeyMQHLMHIZUIDKOO-OKZBNKHCSA-N
SMILESCCC(C)(C)c1ccc(C[C@H](C)CN2C[C@H](C)O[C@H](C)C2)cc1

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.

  • (+/-)-CIS-2,6-DIMETHYL-4-(2-METHYL-3-(P-TERT-PENTYLPHENYL)PROPYL)MORPHOLINE
  • AB0BHP2FH0
  • Amorolfina
  • Amorolfinum
  • Morpholine, 4-(3-(4-(1,1-dimethylpropyl)phenyl)-2-methylpropyl)-2,6-dimethyl-, cis-, (+-)-
  • Morpholine, 4-[(2S)-3-[4-(1,1-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethyl-, (2R,6S)-
  • Ro 14-4767
  • Ro 14-4767/000
  • Ro-14-4767/000
  • morpholine, 4-(3-(4-(1,1-dimethylpropyl)phenyl)-2-methylpropyl)-2,6-dimethyl-, cis-, (+/-)-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13512584
  • UNII-AB0BHP2FH0

Physico-Chemical properties

IUPAC name(2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine
Molecular formulaC21H35NO
Molecular weight317.509
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity104.53
LogP4.6
Topological polar surface area12.5

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.