tamoxifen N-beta-D-glucosiduronic acid

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

What is the tamoxifen N-beta-D-glucosiduronic acid?

The molecule tamoxifen N-beta-D-glucosiduronic acid presents a molecular formula of C32H38NO7+ and its IUPAC name is [(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-dimethylazanium.

Tamoxifen is a synthetic hormone that is used to treat breast cancer. It is a member of the class of drugs known as selective estrogen receptor modulators (SERMs). Tamoxifen works by binding to the estrogen receptor and blocking the effects of estrogen on breast tissue. This can prevent the growth of breast cancer cells..

Tamoxifen was first synthesized in 1962 by ICI Pharmaceuticals. It was approved for use in the United States in 1977. Tamoxifen is typically taken orally, but it can also be given intravenously. The most common side effects of tamoxifen are hot flashes, vaginal dryness, and nausea..

Tamoxifen is generally well-tolerated. However, there are some potential risks associated with its use. These include an increased risk of blood clots, stroke, and endometrial cancer. Tamoxifen may also increase the risk of developing certain types of breast cancer..

Despite these potential risks, tamoxifen is still considered an effective treatment for breast cancer. It is often used as a first-line treatment for hormone-positive breast cancer. Tamoxifen may also be used to prevent breast cancer in women who are at high risk for the disease..

3D structure

Cartesian coordinates

Geometry of tamoxifen N-beta-D-glucosiduronic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

tamoxifen N-beta-D-glucosiduronic acid UKFQQYJAYUAYES-DTMHFWPESA-O chemical compound 2D structure molecule svg
tamoxifen N-beta-D-glucosiduronic acid

 

Molecule descriptors

 
IUPAC name[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-dimethylazanium
InChI codeInChI=1S/C32H37NO7/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)39-20-19-33(2,3)31-29(36)27(34)28(35)30(40-31)32(37)38/h5-18,27-31,34-36H,4,19-20H2,1-3H3/p+1/b26-25-/t27-,28-,29+,30-,31+/m0/s1
InChI KeyUKFQQYJAYUAYES-DTMHFWPESA-O
SMILESCC/C(=C(\c1ccccc1)c1ccc(OCC[N+](C)(C)[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)cc1)c1ccccc1

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.

  • N-(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)-N,N-dimethyl-beta-D-glucopyranuronosylaminium
  • Q26997414
  • Tamoxifen-N-glucuronide
  • [(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-dimethylazanium
  • tamoxifen N-beta-D-glucosiduronic acid
  • tamoxifen N-glucuronide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC64622628
  • DTXSID101343474
  • CHEBI:32663

Physico-Chemical properties

IUPAC name[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-dimethylazanium
Molecular formulaC32H38NO7+
Molecular weight548.647
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity152.27
LogP3.4
Topological polar surface area116.5

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.